JPS641469B2 - - Google Patents
Info
- Publication number
- JPS641469B2 JPS641469B2 JP54132783A JP13278379A JPS641469B2 JP S641469 B2 JPS641469 B2 JP S641469B2 JP 54132783 A JP54132783 A JP 54132783A JP 13278379 A JP13278379 A JP 13278379A JP S641469 B2 JPS641469 B2 JP S641469B2
- Authority
- JP
- Japan
- Prior art keywords
- formula
- group
- nitrobenzyl
- chlorosulfinyl
- methyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- -1 penicillin sulfoxide ester Chemical class 0.000 claims description 164
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 77
- 238000000034 method Methods 0.000 claims description 51
- 229920000642 polymer Polymers 0.000 claims description 46
- 125000006503 p-nitrobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1[N+]([O-])=O)C([H])([H])* 0.000 claims description 43
- 238000004519 manufacturing process Methods 0.000 claims description 33
- 238000006243 chemical reaction Methods 0.000 claims description 27
- 150000001875 compounds Chemical class 0.000 claims description 24
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 claims description 23
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 21
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 20
- 239000003795 chemical substances by application Substances 0.000 claims description 19
- 229920002717 polyvinylpyridine Polymers 0.000 claims description 16
- WDRFYIPWHMGQPN-UHFFFAOYSA-N 2-chloroisoindole-1,3-dione Chemical group C1=CC=C2C(=O)N(Cl)C(=O)C2=C1 WDRFYIPWHMGQPN-UHFFFAOYSA-N 0.000 claims description 15
- 239000003960 organic solvent Substances 0.000 claims description 14
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 12
- FCZNNHHXCFARDY-WQRUCBPWSA-N (2s,5r,6r)-3,3-dimethyl-4,7-dioxo-6-[(2-phenylacetyl)amino]-4$l^{4}-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid Chemical compound N([C@H]1[C@@H]2N(C1=O)[C@H](C(S2=O)(C)C)C(O)=O)C(=O)CC1=CC=CC=C1 FCZNNHHXCFARDY-WQRUCBPWSA-N 0.000 claims description 11
- 125000006244 carboxylic acid protecting group Chemical group 0.000 claims description 11
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 11
- KDXFMMHNGFNJFA-UHFFFAOYSA-N 4-oxoazetidine-2-sulfinyl chloride Chemical compound ClS(=O)C1CC(=O)N1 KDXFMMHNGFNJFA-UHFFFAOYSA-N 0.000 claims description 9
- 125000000453 2,2,2-trichloroethyl group Chemical group [H]C([H])(*)C(Cl)(Cl)Cl 0.000 claims description 8
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 8
- 229920000075 poly(4-vinylpyridine) Polymers 0.000 claims description 8
- 150000001732 carboxylic acid derivatives Chemical group 0.000 claims description 7
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 7
- KFDVPJUYSDEJTH-UHFFFAOYSA-N 4-ethenylpyridine Chemical compound C=CC1=CC=NC=C1 KFDVPJUYSDEJTH-UHFFFAOYSA-N 0.000 claims description 6
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 6
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 5
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 5
- 125000002030 1,2-phenylene group Chemical group [H]C1=C([H])C([*:1])=C([*:2])C([H])=C1[H] 0.000 claims description 4
- 239000000460 chlorine Substances 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- ZIUHHBKFKCYYJD-UHFFFAOYSA-N n,n'-methylenebisacrylamide Chemical compound C=CC(=O)NCNC(=O)C=C ZIUHHBKFKCYYJD-UHFFFAOYSA-N 0.000 claims description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims description 4
- HEWUUUAOFGCFHK-UHFFFAOYSA-N 2-oxoazetidine-1-sulfinyl chloride Chemical compound ClS(=O)N1CCC1=O HEWUUUAOFGCFHK-UHFFFAOYSA-N 0.000 claims description 3
- 125000004217 4-methoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1OC([H])([H])[H])C([H])([H])* 0.000 claims description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 3
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 3
- 125000005982 diphenylmethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 3
- 125000004970 halomethyl group Chemical group 0.000 claims description 3
- 239000008096 xylene Substances 0.000 claims description 3
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims description 2
- TURITJIWSQEMDB-UHFFFAOYSA-N 2-methyl-n-[(2-methylprop-2-enoylamino)methyl]prop-2-enamide Chemical compound CC(=C)C(=O)NCNC(=O)C(C)=C TURITJIWSQEMDB-UHFFFAOYSA-N 0.000 claims description 2
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 2
- 125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 claims description 2
- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 claims description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 125000000623 heterocyclic group Chemical group 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- 125000004434 sulfur atom Chemical group 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 2
- 229910052794 bromium Inorganic materials 0.000 claims 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 72
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 47
- 229920001577 copolymer Polymers 0.000 description 38
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 35
- 229910021627 Tin(IV) chloride Inorganic materials 0.000 description 25
- 239000000047 product Substances 0.000 description 25
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 25
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 24
- MNFORVFSTILPAW-UHFFFAOYSA-N azetidin-2-one Chemical compound O=C1CCN1 MNFORVFSTILPAW-UHFFFAOYSA-N 0.000 description 23
- 238000004132 cross linking Methods 0.000 description 23
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 21
- 239000000725 suspension Substances 0.000 description 21
- 238000010992 reflux Methods 0.000 description 17
- 239000003446 ligand Substances 0.000 description 16
- 239000000203 mixture Substances 0.000 description 16
- 239000000706 filtrate Substances 0.000 description 15
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 15
- 238000001914 filtration Methods 0.000 description 14
- 125000006239 protecting group Chemical group 0.000 description 14
- 239000000243 solution Substances 0.000 description 13
- 238000010438 heat treatment Methods 0.000 description 12
- 239000002245 particle Substances 0.000 description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 11
- 239000003431 cross linking reagent Substances 0.000 description 11
- KGIGUEBEKRSTEW-UHFFFAOYSA-N 2-vinylpyridine Chemical compound C=CC1=CC=CC=N1 KGIGUEBEKRSTEW-UHFFFAOYSA-N 0.000 description 10
- 229930182555 Penicillin Natural products 0.000 description 10
- 150000002148 esters Chemical class 0.000 description 10
- 229940049954 penicillin Drugs 0.000 description 10
- 239000012429 reaction media Substances 0.000 description 10
- 239000007858 starting material Substances 0.000 description 10
- 238000003756 stirring Methods 0.000 description 10
- 229920006037 cross link polymer Polymers 0.000 description 9
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 9
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 9
- 239000002904 solvent Substances 0.000 description 9
- 150000003462 sulfoxides Chemical class 0.000 description 9
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 8
- 238000004821 distillation Methods 0.000 description 8
- XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical compound C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 description 8
- 239000002253 acid Substances 0.000 description 7
- 229940124587 cephalosporin Drugs 0.000 description 7
- 239000003153 chemical reaction reagent Substances 0.000 description 7
- 239000002002 slurry Substances 0.000 description 7
- 229930186147 Cephalosporin Natural products 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 239000003242 anti bacterial agent Substances 0.000 description 6
- 229940088710 antibiotic agent Drugs 0.000 description 6
- 150000001780 cephalosporins Chemical class 0.000 description 6
- 230000008961 swelling Effects 0.000 description 6
- 238000005406 washing Methods 0.000 description 6
- 150000003952 β-lactams Chemical class 0.000 description 6
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 5
- 125000003118 aryl group Chemical group 0.000 description 5
- 239000011324 bead Substances 0.000 description 5
- 239000000155 melt Substances 0.000 description 5
- 238000006116 polymerization reaction Methods 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- WIMGCNFCFYONPX-UHFFFAOYSA-N (4-nitrophenyl)methyl 2-[2-chlorosulfinyl-4-oxo-3-[(2-phenoxyacetyl)amino]azetidin-1-yl]-3-methylbut-3-enoate Chemical compound C=1C=C([N+]([O-])=O)C=CC=1COC(=O)C(C(=C)C)N(C1=O)C(S(Cl)=O)C1NC(=O)COC1=CC=CC=C1 WIMGCNFCFYONPX-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- JRNVZBWKYDBUCA-UHFFFAOYSA-N N-chlorosuccinimide Chemical compound ClN1C(=O)CCC1=O JRNVZBWKYDBUCA-UHFFFAOYSA-N 0.000 description 4
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 4
- 239000012320 chlorinating reagent Substances 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 229920005989 resin Polymers 0.000 description 4
- 239000011347 resin Substances 0.000 description 4
- 238000007363 ring formation reaction Methods 0.000 description 4
- 235000002639 sodium chloride Nutrition 0.000 description 4
- 239000011780 sodium chloride Substances 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- PTTPXKJBFFKCEK-UHFFFAOYSA-N 2-Methyl-4-heptanone Chemical compound CC(C)CC(=O)CC(C)C PTTPXKJBFFKCEK-UHFFFAOYSA-N 0.000 description 3
- 239000004971 Cross linker Substances 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- OGEBVIRSYGXOGZ-GELUPKEKSA-N O=S1C(C)(C)C(C(O)=O)N2C(=O)C[C@H]21 Chemical compound O=S1C(C)(C)C(C(O)=O)N2C(=O)C[C@H]21 OGEBVIRSYGXOGZ-GELUPKEKSA-N 0.000 description 3
- 230000002378 acidificating effect Effects 0.000 description 3
- 150000001408 amides Chemical class 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- AOESAXAWXYJFNC-UHFFFAOYSA-N bis(prop-2-enyl) propanedioate Chemical compound C=CCOC(=O)CC(=O)OCC=C AOESAXAWXYJFNC-UHFFFAOYSA-N 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 3
- 125000004185 ester group Chemical group 0.000 description 3
- 239000012442 inert solvent Substances 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- HRDXJKGNWSUIBT-UHFFFAOYSA-N methoxybenzene Chemical group [CH2]OC1=CC=CC=C1 HRDXJKGNWSUIBT-UHFFFAOYSA-N 0.000 description 3
- 239000000178 monomer Substances 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 3
- UBOXGVDOUJQMTN-UHFFFAOYSA-N 1,1,2-trichloroethane Chemical compound ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 description 2
- FCMUPMSEVHVOSE-UHFFFAOYSA-N 2,3-bis(ethenyl)pyridine Chemical compound C=CC1=CC=CN=C1C=C FCMUPMSEVHVOSE-UHFFFAOYSA-N 0.000 description 2
- HWSSEYVMGDIFMH-UHFFFAOYSA-N 2-[2-[2-(2-methylprop-2-enoyloxy)ethoxy]ethoxy]ethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCOCCOCCOC(=O)C(C)=C HWSSEYVMGDIFMH-UHFFFAOYSA-N 0.000 description 2
- KUDUQBURMYMBIJ-UHFFFAOYSA-N 2-prop-2-enoyloxyethyl prop-2-enoate Chemical compound C=CC(=O)OCCOC(=O)C=C KUDUQBURMYMBIJ-UHFFFAOYSA-N 0.000 description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
- SYBYTAAJFKOIEJ-UHFFFAOYSA-N 3-Methylbutan-2-one Chemical compound CC(C)C(C)=O SYBYTAAJFKOIEJ-UHFFFAOYSA-N 0.000 description 2
- APOAEMIYHVGWEZ-UHFFFAOYSA-N 4-chloroisoindole-1,3-dione Chemical compound ClC1=CC=CC2=C1C(=O)NC2=O APOAEMIYHVGWEZ-UHFFFAOYSA-N 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- QDHHCQZDFGDHMP-UHFFFAOYSA-N Chloramine Chemical class ClN QDHHCQZDFGDHMP-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 2
- 238000005727 Friedel-Crafts reaction Methods 0.000 description 2
- KWYHDKDOAIKMQN-UHFFFAOYSA-N N,N,N',N'-tetramethylethylenediamine Chemical compound CN(C)CCN(C)C KWYHDKDOAIKMQN-UHFFFAOYSA-N 0.000 description 2
- FZERHIULMFGESH-UHFFFAOYSA-N N-phenylacetamide Chemical compound CC(=O)NC1=CC=CC=C1 FZERHIULMFGESH-UHFFFAOYSA-N 0.000 description 2
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 2
- KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 125000002947 alkylene group Chemical group 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 2
- 239000003125 aqueous solvent Substances 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 238000010533 azeotropic distillation Methods 0.000 description 2
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- BRPQOXSCLDDYGP-UHFFFAOYSA-N calcium oxide Chemical compound [O-2].[Ca+2] BRPQOXSCLDDYGP-UHFFFAOYSA-N 0.000 description 2
- 239000000292 calcium oxide Substances 0.000 description 2
- ODINCKMPIJJUCX-UHFFFAOYSA-N calcium oxide Inorganic materials [Ca]=O ODINCKMPIJJUCX-UHFFFAOYSA-N 0.000 description 2
- 235000013877 carbamide Nutrition 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 150000001768 cations Chemical class 0.000 description 2
- 229920006026 co-polymeric resin Polymers 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 description 2
- 150000003997 cyclic ketones Chemical class 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- BGTOWKSIORTVQH-UHFFFAOYSA-N cyclopentanone Chemical compound O=C1CCCC1 BGTOWKSIORTVQH-UHFFFAOYSA-N 0.000 description 2
- ZZVUWRFHKOJYTH-UHFFFAOYSA-N diphenhydramine Chemical group C=1C=CC=CC=1C(OCCN(C)C)C1=CC=CC=C1 ZZVUWRFHKOJYTH-UHFFFAOYSA-N 0.000 description 2
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 2
- ICDQOGMPYSAZFB-UHFFFAOYSA-N ethyl n-chlorocarbamate Chemical class CCOC(=O)NCl ICDQOGMPYSAZFB-UHFFFAOYSA-N 0.000 description 2
- 239000004744 fabric Substances 0.000 description 2
- 150000008282 halocarbons Chemical class 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- 238000007327 hydrogenolysis reaction Methods 0.000 description 2
- 150000003949 imides Chemical class 0.000 description 2
- CDOSHBSSFJOMGT-UHFFFAOYSA-N linalool Chemical compound CC(C)=CCCC(C)(O)C=C CDOSHBSSFJOMGT-UHFFFAOYSA-N 0.000 description 2
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 2
- 235000019341 magnesium sulphate Nutrition 0.000 description 2
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 2
- 239000012299 nitrogen atmosphere Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- XNLICIUVMPYHGG-UHFFFAOYSA-N pentan-2-one Chemical compound CCCC(C)=O XNLICIUVMPYHGG-UHFFFAOYSA-N 0.000 description 2
- 229920002451 polyvinyl alcohol Polymers 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- JQWHASGSAFIOCM-UHFFFAOYSA-M sodium periodate Chemical compound [Na+].[O-]I(=O)(=O)=O JQWHASGSAFIOCM-UHFFFAOYSA-M 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 229940124530 sulfonamide Drugs 0.000 description 2
- 150000003456 sulfonamides Chemical class 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- 125000006000 trichloroethyl group Chemical group 0.000 description 2
- UAXOELSVPTZZQG-UHFFFAOYSA-N trimethyl acrylic acid Chemical compound CC(C)=C(C)C(O)=O UAXOELSVPTZZQG-UHFFFAOYSA-N 0.000 description 2
- 150000003672 ureas Chemical class 0.000 description 2
- 150000003673 urethanes Chemical class 0.000 description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
- 229920002554 vinyl polymer Polymers 0.000 description 2
- UQZAJTVPMYOIDG-UHFFFAOYSA-N (3-chlorophenyl) n-chloro-n-methylcarbamate Chemical compound CN(Cl)C(=O)OC1=CC=CC(Cl)=C1 UQZAJTVPMYOIDG-UHFFFAOYSA-N 0.000 description 1
- DXIXQMDZEZETJS-UHFFFAOYSA-N (4-methylphenyl) n-chlorocarbamate Chemical compound CC1=CC=C(OC(=O)NCl)C=C1 DXIXQMDZEZETJS-UHFFFAOYSA-N 0.000 description 1
- PTRQIKNYGHTICI-UHFFFAOYSA-N (4-nitrophenyl)methyl 2-[2-chlorosulfinyl-4-oxo-3-[(2-phenylacetyl)amino]azetidin-1-yl]-3-methylbut-3-enoate Chemical compound C=1C=C([N+]([O-])=O)C=CC=1COC(=O)C(C(=C)C)N(C1=O)C(S(Cl)=O)C1NC(=O)CC1=CC=CC=C1 PTRQIKNYGHTICI-UHFFFAOYSA-N 0.000 description 1
- SEPPVOUBHWNCAW-FNORWQNLSA-N (E)-4-oxonon-2-enal Chemical compound CCCCCC(=O)\C=C\C=O SEPPVOUBHWNCAW-FNORWQNLSA-N 0.000 description 1
- NWRZGFYWENINNX-UHFFFAOYSA-N 1,1,2-tris(ethenyl)cyclohexane Chemical compound C=CC1CCCCC1(C=C)C=C NWRZGFYWENINNX-UHFFFAOYSA-N 0.000 description 1
- FYADHXFMURLYQI-UHFFFAOYSA-N 1,2,4-triazine Chemical compound C1=CN=NC=N1 FYADHXFMURLYQI-UHFFFAOYSA-N 0.000 description 1
- UWMQSTWNWSCJFT-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;2-ethenylpyridine Chemical compound C=CC1=CC=CC=N1.C=CC1=CC=CC=C1C=C UWMQSTWNWSCJFT-UHFFFAOYSA-N 0.000 description 1
- PAAZPARNPHGIKF-UHFFFAOYSA-N 1,2-dibromoethane Chemical compound BrCCBr PAAZPARNPHGIKF-UHFFFAOYSA-N 0.000 description 1
- KOMNUTZXSVSERR-UHFFFAOYSA-N 1,3,5-tris(prop-2-enyl)-1,3,5-triazinane-2,4,6-trione Chemical compound C=CCN1C(=O)N(CC=C)C(=O)N(CC=C)C1=O KOMNUTZXSVSERR-UHFFFAOYSA-N 0.000 description 1
- MDBJCGQXJIHVHH-UHFFFAOYSA-N 1,3-dichloro-1,3-dicyclohexylurea Chemical compound C1CCCCC1N(Cl)C(=O)N(Cl)C1CCCCC1 MDBJCGQXJIHVHH-UHFFFAOYSA-N 0.000 description 1
- LYBJXVMKLFINFS-UHFFFAOYSA-N 1,3-dichloro-1,3-diphenylurea Chemical compound C=1C=CC=CC=1N(Cl)C(=O)N(Cl)C1=CC=CC=C1 LYBJXVMKLFINFS-UHFFFAOYSA-N 0.000 description 1
- FNCSJAFFQNJYRQ-UHFFFAOYSA-N 1,3-dichloro-1-(3-chlorophenyl)-3-methylurea Chemical compound CN(Cl)C(=O)N(Cl)C1=CC=CC(Cl)=C1 FNCSJAFFQNJYRQ-UHFFFAOYSA-N 0.000 description 1
- MJBAWHUBZXMVOC-UHFFFAOYSA-N 1,3-dichloro-1-(4-methylphenyl)-3-propan-2-ylurea Chemical compound CC(C)N(Cl)C(=O)N(Cl)C1=CC=C(C)C=C1 MJBAWHUBZXMVOC-UHFFFAOYSA-N 0.000 description 1
- HGUWAJIBWQYNAV-UHFFFAOYSA-N 1,3-dichloro-1-(4-methylphenyl)urea Chemical compound CC1=CC=C(N(Cl)C(=O)NCl)C=C1 HGUWAJIBWQYNAV-UHFFFAOYSA-N 0.000 description 1
- DZVQYJTYQVGELN-UHFFFAOYSA-N 1,3-dichloro-1-cyclohexyl-3-(4-nitrophenyl)urea Chemical compound C1=CC([N+](=O)[O-])=CC=C1N(Cl)C(=O)N(Cl)C1CCCCC1 DZVQYJTYQVGELN-UHFFFAOYSA-N 0.000 description 1
- PGAJRUFQINAARK-UHFFFAOYSA-N 1,3-dichloro-1-cyclohexyl-3-ethylurea Chemical compound CCN(Cl)C(=O)N(Cl)C1CCCCC1 PGAJRUFQINAARK-UHFFFAOYSA-N 0.000 description 1
- GOVGRIDEZYYAEV-UHFFFAOYSA-N 1,3-dichloro-1-methylurea Chemical compound CN(Cl)C(=O)NCl GOVGRIDEZYYAEV-UHFFFAOYSA-N 0.000 description 1
- OOUCRJBCRWRTKG-UHFFFAOYSA-N 1,3-dichloro-1-phenyl-3-propylurea Chemical compound CCCN(Cl)C(=O)N(Cl)C1=CC=CC=C1 OOUCRJBCRWRTKG-UHFFFAOYSA-N 0.000 description 1
- TUQCXXYUMOIHKA-UHFFFAOYSA-N 1,3-dichloro-1-phenylurea Chemical compound ClNC(=O)N(Cl)C1=CC=CC=C1 TUQCXXYUMOIHKA-UHFFFAOYSA-N 0.000 description 1
- CHAQCCZFQZMBCQ-UHFFFAOYSA-N 1,4-bis(prop-2-enyl)piperazine Chemical group C=CCN1CCN(CC=C)CC1 CHAQCCZFQZMBCQ-UHFFFAOYSA-N 0.000 description 1
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 1
- ADFIFDHDLIZVFW-UHFFFAOYSA-N 1-chloropiperidine-2,6-dione Chemical compound ClN1C(=O)CCCC1=O ADFIFDHDLIZVFW-UHFFFAOYSA-N 0.000 description 1
- MNZAKDODWSQONA-UHFFFAOYSA-N 1-dibutylphosphorylbutane Chemical compound CCCCP(=O)(CCCC)CCCC MNZAKDODWSQONA-UHFFFAOYSA-N 0.000 description 1
- ZSSWXNPRLJLCDU-UHFFFAOYSA-N 1-diethylphosphorylethane Chemical compound CCP(=O)(CC)CC ZSSWXNPRLJLCDU-UHFFFAOYSA-N 0.000 description 1
- SNZSAFILJOCMFM-UHFFFAOYSA-N 1-dipropylphosphorylpropane Chemical compound CCCP(=O)(CCC)CCC SNZSAFILJOCMFM-UHFFFAOYSA-N 0.000 description 1
- SBZMRQRLGDOPQJ-UHFFFAOYSA-N 2,2,2-trichloroethyl 2-(2-chlorosulfinyl-3-formamido-4-oxoazetidin-1-yl)-3-methylbut-3-enoate Chemical compound ClC(Cl)(Cl)COC(=O)C(C(=C)C)N1C(S(Cl)=O)C(NC=O)C1=O SBZMRQRLGDOPQJ-UHFFFAOYSA-N 0.000 description 1
- XRWSDTNCPCQCIW-UHFFFAOYSA-N 2,4-bis(ethenyl)-6-methylpyridine Chemical compound CC1=CC(C=C)=CC(C=C)=N1 XRWSDTNCPCQCIW-UHFFFAOYSA-N 0.000 description 1
- AYKSPIBLOMDDGD-UHFFFAOYSA-N 2-(chlorocarbamoyl)benzenesulfonic acid Chemical compound ClN=C(O)C1=CC=CC=C1S(O)(=O)=O AYKSPIBLOMDDGD-UHFFFAOYSA-N 0.000 description 1
- JEJIWKKGUFJLAF-UHFFFAOYSA-N 2-(hydroxymethyl)-2-methylpropane-1,3-diol;2-methylprop-2-enoic acid Chemical group CC(=C)C(O)=O.CC(=C)C(O)=O.CC(=C)C(O)=O.OCC(C)(CO)CO JEJIWKKGUFJLAF-UHFFFAOYSA-N 0.000 description 1
- HEDHCJIWNGIQLU-UHFFFAOYSA-N 2-[2-chlorosulfinyl-3-[[2-(4-methylphenoxy)acetyl]amino]-4-oxoazetidin-1-yl]-3-methyl-2-[(4-nitrophenyl)methyl]but-3-enoic acid Chemical compound CC1=CC=C(C=C1)OCC(=O)NC2C(N(C2=O)C(CC3=CC=C(C=C3)[N+](=O)[O-])(C(=C)C)C(=O)O)S(=O)Cl HEDHCJIWNGIQLU-UHFFFAOYSA-N 0.000 description 1
- 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 description 1
- AOPRXJXHLWYPQR-UHFFFAOYSA-N 2-phenoxyacetamide Chemical group NC(=O)COC1=CC=CC=C1 AOPRXJXHLWYPQR-UHFFFAOYSA-N 0.000 description 1
- SMTDFMMXJHYDDE-UHFFFAOYSA-N 2-prop-1-enylpyridine Chemical compound CC=CC1=CC=CC=N1 SMTDFMMXJHYDDE-UHFFFAOYSA-N 0.000 description 1
- 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 description 1
- YNJSNEKCXVFDKW-UHFFFAOYSA-N 3-(5-amino-1h-indol-3-yl)-2-azaniumylpropanoate Chemical compound C1=C(N)C=C2C(CC(N)C(O)=O)=CNC2=C1 YNJSNEKCXVFDKW-UHFFFAOYSA-N 0.000 description 1
- BXAAQNFGSQKPDZ-UHFFFAOYSA-N 3-[1,2,2-tris(prop-2-enoxy)ethoxy]prop-1-ene Chemical compound C=CCOC(OCC=C)C(OCC=C)OCC=C BXAAQNFGSQKPDZ-UHFFFAOYSA-N 0.000 description 1
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 1
- DPZYLEIWHTWHCU-UHFFFAOYSA-N 3-ethenylpyridine Chemical compound C=CC1=CC=CN=C1 DPZYLEIWHTWHCU-UHFFFAOYSA-N 0.000 description 1
- NZFIRLLOEUJXNX-UHFFFAOYSA-N 4-(chloroamino)-4-oxobutane-1-sulfonic acid Chemical compound ClN=C(O)CCCS(O)(=O)=O NZFIRLLOEUJXNX-UHFFFAOYSA-N 0.000 description 1
- FFOLJFOMOFZLPG-UHFFFAOYSA-N 4-ethenyl-2-methylpyridine Chemical compound CC1=CC(C=C)=CC=N1 FFOLJFOMOFZLPG-UHFFFAOYSA-N 0.000 description 1
- OHFQAZVYTLCHMK-UHFFFAOYSA-N 4-ethenyl-3-methylpyridine Chemical compound CC1=CN=CC=C1C=C OHFQAZVYTLCHMK-UHFFFAOYSA-N 0.000 description 1
- JTVRUPKOGWGRSQ-UHFFFAOYSA-N 4-ethenylpyridine;n-[(prop-2-enoylamino)methyl]prop-2-enamide Chemical compound C=CC1=CC=NC=C1.C=CC(=O)NCNC(=O)C=C JTVRUPKOGWGRSQ-UHFFFAOYSA-N 0.000 description 1
- 125000006181 4-methyl benzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])C([H])([H])* 0.000 description 1
- LLBZPESJRQGYMB-UHFFFAOYSA-N 4-one Natural products O1C(C(=O)CC)CC(C)C11C2(C)CCC(C3(C)C(C(C)(CO)C(OC4C(C(O)C(O)C(COC5C(C(O)C(O)CO5)OC5C(C(OC6C(C(O)C(O)C(CO)O6)O)C(O)C(CO)O5)OC5C(C(O)C(O)C(C)O5)O)O4)O)CC3)CC3)=C3C2(C)CC1 LLBZPESJRQGYMB-UHFFFAOYSA-N 0.000 description 1
- 125000004199 4-trifluoromethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C(F)(F)F 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- GTVMTEBICVETFJ-UHFFFAOYSA-N C(C(=C)C)(=O)O.C(C(=C)C)(=O)O.C(C(=C)C)(=O)O.C(O)C(CC)(CO)CO.C(C=C)(=O)O.C(C=C)(=O)O.C(C=C)(=O)O.C(O)C(CC)(CO)CO Chemical group C(C(=C)C)(=O)O.C(C(=C)C)(=O)O.C(C(=C)C)(=O)O.C(O)C(CC)(CO)CO.C(C=C)(=O)O.C(C=C)(=O)O.C(C=C)(=O)O.C(O)C(CC)(CO)CO GTVMTEBICVETFJ-UHFFFAOYSA-N 0.000 description 1
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- WHTNHYRHHHFFBV-UHFFFAOYSA-N ClNS(=O)=O Chemical class ClNS(=O)=O WHTNHYRHHHFFBV-UHFFFAOYSA-N 0.000 description 1
- 239000004641 Diallyl-phthalate Substances 0.000 description 1
- YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 description 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 1
- 238000005684 Liebig rearrangement reaction Methods 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical class CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
- WRQNANDWMGAFTP-UHFFFAOYSA-N Methylacetoacetic acid Chemical compound COC(=O)CC(C)=O WRQNANDWMGAFTP-UHFFFAOYSA-N 0.000 description 1
- NXTVQNIVUKXOIL-UHFFFAOYSA-N N-chlorotoluene-p-sulfonamide Chemical compound CC1=CC=C(S(=O)(=O)NCl)C=C1 NXTVQNIVUKXOIL-UHFFFAOYSA-N 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical group [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 1
- XAKBSHICSHRJCL-UHFFFAOYSA-N [CH2]C(=O)C1=CC=CC=C1 Chemical group [CH2]C(=O)C1=CC=CC=C1 XAKBSHICSHRJCL-UHFFFAOYSA-N 0.000 description 1
- 229960001413 acetanilide Drugs 0.000 description 1
- 238000005903 acid hydrolysis reaction Methods 0.000 description 1
- 150000003926 acrylamides Chemical class 0.000 description 1
- 229920006397 acrylic thermoplastic Polymers 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000003368 amide group Chemical group 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- 230000000845 anti-microbial effect Effects 0.000 description 1
- 239000000010 aprotic solvent Substances 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 150000008378 aryl ethers Chemical class 0.000 description 1
- NXZNZQNGYFJVAS-UHFFFAOYSA-N azetidine-1-sulfinyl chloride Chemical compound ClS(=O)N1CCC1 NXZNZQNGYFJVAS-UHFFFAOYSA-N 0.000 description 1
- NGTHFZSNYKQKND-UHFFFAOYSA-N azetidine-2-sulfinyl chloride Chemical compound ClS(=O)C1CCN1 NGTHFZSNYKQKND-UHFFFAOYSA-N 0.000 description 1
- 150000007514 bases Chemical class 0.000 description 1
- BZNUFTUGLKQALE-UHFFFAOYSA-N benzyl 2-[2-chlorosulfinyl-4-oxo-3-[(2-phenylacetyl)amino]azetidin-1-yl]-3-methylbut-3-enoate Chemical compound C=1C=CC=CC=1COC(=O)C(C(=C)C)N(C1=O)C(S(Cl)=O)C1NC(=O)CC1=CC=CC=C1 BZNUFTUGLKQALE-UHFFFAOYSA-N 0.000 description 1
- 230000001588 bifunctional effect Effects 0.000 description 1
- QUDWYFHPNIMBFC-UHFFFAOYSA-N bis(prop-2-enyl) benzene-1,2-dicarboxylate Chemical compound C=CCOC(=O)C1=CC=CC=C1C(=O)OCC=C QUDWYFHPNIMBFC-UHFFFAOYSA-N 0.000 description 1
- HABAXTXIECRCKH-UHFFFAOYSA-N bis(prop-2-enyl) butanedioate Chemical compound C=CCOC(=O)CCC(=O)OCC=C HABAXTXIECRCKH-UHFFFAOYSA-N 0.000 description 1
- 125000005997 bromomethyl group Chemical group 0.000 description 1
- 239000001110 calcium chloride Substances 0.000 description 1
- 229910001628 calcium chloride Inorganic materials 0.000 description 1
- 235000011148 calcium chloride Nutrition 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 235000013351 cheese Nutrition 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 238000002485 combustion reaction Methods 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- KDTAEYOYAZPLIC-UHFFFAOYSA-N coumarin 152 Chemical group FC(F)(F)C1=CC(=O)OC2=CC(N(C)C)=CC=C21 KDTAEYOYAZPLIC-UHFFFAOYSA-N 0.000 description 1
- SHQSVMDWKBRBGB-UHFFFAOYSA-N cyclobutanone Chemical compound O=C1CCC1 SHQSVMDWKBRBGB-UHFFFAOYSA-N 0.000 description 1
- CGZZMOTZOONQIA-UHFFFAOYSA-N cycloheptanone Chemical compound O=C1CCCCCC1 CGZZMOTZOONQIA-UHFFFAOYSA-N 0.000 description 1
- NLVXFGVZNJMFDC-UHFFFAOYSA-N cyclohexyl n,n-dichlorocarbamate Chemical compound ClN(Cl)C(=O)OC1CCCCC1 NLVXFGVZNJMFDC-UHFFFAOYSA-N 0.000 description 1
- DSJSTZRIFMQDHV-UHFFFAOYSA-N cyclohexyl n-chloro-n-(4-nitrophenyl)carbamate Chemical compound C1=CC([N+](=O)[O-])=CC=C1N(Cl)C(=O)OC1CCCCC1 DSJSTZRIFMQDHV-UHFFFAOYSA-N 0.000 description 1
- UJUFCZFKGZMCDF-UHFFFAOYSA-N cyclohexyl n-chloro-n-cyclohexylcarbamate Chemical compound C1CCCCC1OC(=O)N(Cl)C1CCCCC1 UJUFCZFKGZMCDF-UHFFFAOYSA-N 0.000 description 1
- 238000010908 decantation Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 238000007257 deesterification reaction Methods 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 239000002274 desiccant Substances 0.000 description 1
- 230000002542 deteriorative effect Effects 0.000 description 1
- 150000001990 dicarboxylic acid derivatives Chemical class 0.000 description 1
- HBGGXOJOCNVPFY-UHFFFAOYSA-N diisononyl phthalate Chemical compound CC(C)CCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCC(C)C HBGGXOJOCNVPFY-UHFFFAOYSA-N 0.000 description 1
- LRMLWYXJORUTBG-UHFFFAOYSA-N dimethylphosphorylmethane Chemical compound CP(C)(C)=O LRMLWYXJORUTBG-UHFFFAOYSA-N 0.000 description 1
- POLCUAVZOMRGSN-UHFFFAOYSA-N dipropyl ether Chemical compound CCCOCCC POLCUAVZOMRGSN-UHFFFAOYSA-N 0.000 description 1
- AFOSIXZFDONLBT-UHFFFAOYSA-N divinyl sulfone Chemical group C=CS(=O)(=O)C=C AFOSIXZFDONLBT-UHFFFAOYSA-N 0.000 description 1
- 238000007720 emulsion polymerization reaction Methods 0.000 description 1
- 150000002081 enamines Chemical class 0.000 description 1
- XYIBRDXRRQCHLP-UHFFFAOYSA-N ethyl acetoacetate Chemical compound CCOC(=O)CC(C)=O XYIBRDXRRQCHLP-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- PCGGNOFZZFFFLU-UHFFFAOYSA-N ethyl n,n-dichlorocarbamate Chemical compound CCOC(=O)N(Cl)Cl PCGGNOFZZFFFLU-UHFFFAOYSA-N 0.000 description 1
- CDPVPXHQPQQRFB-UHFFFAOYSA-N ethyl n-chloro-n-cyclohexylcarbamate Chemical compound CCOC(=O)N(Cl)C1CCCCC1 CDPVPXHQPQQRFB-UHFFFAOYSA-N 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 125000001188 haloalkyl group Chemical group 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 230000002140 halogenating effect Effects 0.000 description 1
- 230000026030 halogenation Effects 0.000 description 1
- 238000005658 halogenation reaction Methods 0.000 description 1
- 238000003621 hammer milling Methods 0.000 description 1
- 239000008241 heterogeneous mixture Substances 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 230000001788 irregular Effects 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 238000011031 large-scale manufacturing process Methods 0.000 description 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
- HXSLDKNUBFXDRG-UHFFFAOYSA-N methyl n,n-dichlorocarbamate Chemical compound COC(=O)N(Cl)Cl HXSLDKNUBFXDRG-UHFFFAOYSA-N 0.000 description 1
- WRWXAONSPQSLTH-UHFFFAOYSA-N methyl n-chlorocarbamate Chemical compound COC(=O)NCl WRWXAONSPQSLTH-UHFFFAOYSA-N 0.000 description 1
- 239000013081 microcrystal Substances 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 239000002808 molecular sieve Substances 0.000 description 1
- 125000006682 monohaloalkyl group Chemical group 0.000 description 1
- APZTZCAKUURTTG-UHFFFAOYSA-N n,3-dichloro-n-methylbenzenesulfonamide Chemical compound CN(Cl)S(=O)(=O)C1=CC=CC(Cl)=C1 APZTZCAKUURTTG-UHFFFAOYSA-N 0.000 description 1
- KZYWTQNZACMDPS-UHFFFAOYSA-N n,4-dichlorobenzamide Chemical compound ClNC(=O)C1=CC=C(Cl)C=C1 KZYWTQNZACMDPS-UHFFFAOYSA-N 0.000 description 1
- BLYOHBPLFYXHQA-UHFFFAOYSA-N n,n-bis(prop-2-enyl)prop-2-enamide Chemical compound C=CCN(CC=C)C(=O)C=C BLYOHBPLFYXHQA-UHFFFAOYSA-N 0.000 description 1
- ARGDYOIRHYLIMT-UHFFFAOYSA-N n,n-dichloro-4-methylbenzenesulfonamide Chemical compound CC1=CC=C(S(=O)(=O)N(Cl)Cl)C=C1 ARGDYOIRHYLIMT-UHFFFAOYSA-N 0.000 description 1
- ROVVHEKSEBLOOM-UHFFFAOYSA-N n,n-dichloroacetamide Chemical compound CC(=O)N(Cl)Cl ROVVHEKSEBLOOM-UHFFFAOYSA-N 0.000 description 1
- PJBJJXCZRAHMCK-UHFFFAOYSA-N n,n-dichlorobenzenesulfonamide Chemical compound ClN(Cl)S(=O)(=O)C1=CC=CC=C1 PJBJJXCZRAHMCK-UHFFFAOYSA-N 0.000 description 1
- DGRUXRBLCZEODA-UHFFFAOYSA-N n,n-dichlorocyclohexanesulfonamide Chemical compound ClN(Cl)S(=O)(=O)C1CCCCC1 DGRUXRBLCZEODA-UHFFFAOYSA-N 0.000 description 1
- GAWNGUCWYPXWOA-UHFFFAOYSA-N n,n-dichloromethanesulfonamide Chemical compound CS(=O)(=O)N(Cl)Cl GAWNGUCWYPXWOA-UHFFFAOYSA-N 0.000 description 1
- WIJTTWJQVXJEFE-UHFFFAOYSA-N n-(3-bromophenyl)-n-chlorobutanamide Chemical compound CCCC(=O)N(Cl)C1=CC=CC(Br)=C1 WIJTTWJQVXJEFE-UHFFFAOYSA-N 0.000 description 1
- OXZMJPQKHGOTGJ-UHFFFAOYSA-N n-[10-(prop-2-enoylamino)decyl]prop-2-enamide Chemical compound C=CC(=O)NCCCCCCCCCCNC(=O)C=C OXZMJPQKHGOTGJ-UHFFFAOYSA-N 0.000 description 1
- DHHIKEVWSRQXQP-UHFFFAOYSA-N n-chloro-4-methylbenzamide Chemical compound CC1=CC=C(C(=O)NCl)C=C1 DHHIKEVWSRQXQP-UHFFFAOYSA-N 0.000 description 1
- DTMXHYUPALBXFG-UHFFFAOYSA-N n-chloro-n,4-dimethylbenzenesulfonamide Chemical compound CN(Cl)S(=O)(=O)C1=CC=C(C)C=C1 DTMXHYUPALBXFG-UHFFFAOYSA-N 0.000 description 1
- KZOXUQBSBWDWQQ-UHFFFAOYSA-N n-chloro-n-(4-methylphenyl)propane-2-sulfonamide Chemical compound CC(C)S(=O)(=O)N(Cl)C1=CC=C(C)C=C1 KZOXUQBSBWDWQQ-UHFFFAOYSA-N 0.000 description 1
- NJTUFLWJRSZJPA-UHFFFAOYSA-N n-chloro-n-(4-nitrophenyl)cyclohexanesulfonamide Chemical compound C1=CC([N+](=O)[O-])=CC=C1N(Cl)S(=O)(=O)C1CCCCC1 NJTUFLWJRSZJPA-UHFFFAOYSA-N 0.000 description 1
- PMXQDTBJZLOVSV-UHFFFAOYSA-N n-chloro-n-cyclohexylacetamide Chemical compound CC(=O)N(Cl)C1CCCCC1 PMXQDTBJZLOVSV-UHFFFAOYSA-N 0.000 description 1
- RWVOAAWFMJRINI-UHFFFAOYSA-N n-chloro-n-cyclohexylbenzenesulfonamide Chemical compound C=1C=CC=CC=1S(=O)(=O)N(Cl)C1CCCCC1 RWVOAAWFMJRINI-UHFFFAOYSA-N 0.000 description 1
- YTYAPSXIGOPIOH-UHFFFAOYSA-N n-chloro-n-cyclohexylcyclohexanesulfonamide Chemical compound C1CCCCC1S(=O)(=O)N(Cl)C1CCCCC1 YTYAPSXIGOPIOH-UHFFFAOYSA-N 0.000 description 1
- YEXVRBUZIOSARW-UHFFFAOYSA-N n-chloro-n-cyclohexylethanesulfonamide Chemical compound CCS(=O)(=O)N(Cl)C1CCCCC1 YEXVRBUZIOSARW-UHFFFAOYSA-N 0.000 description 1
- FGJCTKGHKMARPX-UHFFFAOYSA-N n-chloro-n-ethyl-3-nitrobenzenesulfonamide Chemical compound CCN(Cl)S(=O)(=O)C1=CC=CC([N+]([O-])=O)=C1 FGJCTKGHKMARPX-UHFFFAOYSA-N 0.000 description 1
- XPTJWKPOBFHDHX-UHFFFAOYSA-N n-chloro-n-ethylbenzamide Chemical compound CCN(Cl)C(=O)C1=CC=CC=C1 XPTJWKPOBFHDHX-UHFFFAOYSA-N 0.000 description 1
- DQJKBIDVOSQVEV-UHFFFAOYSA-N n-chloro-n-methylacetamide Chemical compound CN(Cl)C(C)=O DQJKBIDVOSQVEV-UHFFFAOYSA-N 0.000 description 1
- WQJHFILPJKSLJW-UHFFFAOYSA-N n-chloro-n-phenylbenzenesulfonamide Chemical compound C=1C=CC=CC=1S(=O)(=O)N(Cl)C1=CC=CC=C1 WQJHFILPJKSLJW-UHFFFAOYSA-N 0.000 description 1
- RKLUHJIBJTXOQU-UHFFFAOYSA-N n-chloro-n-phenylpropanamide Chemical compound CCC(=O)N(Cl)C1=CC=CC=C1 RKLUHJIBJTXOQU-UHFFFAOYSA-N 0.000 description 1
- UFICRBPXWFJZFC-UHFFFAOYSA-N n-chloro-n-propylbenzenesulfonamide Chemical compound CCCN(Cl)S(=O)(=O)C1=CC=CC=C1 UFICRBPXWFJZFC-UHFFFAOYSA-N 0.000 description 1
- HSPSCWZIJWKZKD-UHFFFAOYSA-N n-chloroacetamide Chemical compound CC(=O)NCl HSPSCWZIJWKZKD-UHFFFAOYSA-N 0.000 description 1
- CHVZPRDGLWBEMJ-UHFFFAOYSA-N n-chlorobenzenesulfonamide Chemical compound ClNS(=O)(=O)C1=CC=CC=C1 CHVZPRDGLWBEMJ-UHFFFAOYSA-N 0.000 description 1
- QQZCYGRKEOWFAG-UHFFFAOYSA-N n-chlorocyclohexanecarboxamide Chemical compound ClNC(=O)C1CCCCC1 QQZCYGRKEOWFAG-UHFFFAOYSA-N 0.000 description 1
- KFKMOYYBYVVHQQ-UHFFFAOYSA-N n-chloromethanesulfonamide Chemical compound CS(=O)(=O)NCl KFKMOYYBYVVHQQ-UHFFFAOYSA-N 0.000 description 1
- UPSNOKIUEULXHF-UHFFFAOYSA-N n-chloropropanamide Chemical compound CCC(=O)NCl UPSNOKIUEULXHF-UHFFFAOYSA-N 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 150000004967 organic peroxy acids Chemical class 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
- 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 description 1
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
- DLRJIFUOBPOJNS-UHFFFAOYSA-N phenetole Chemical compound CCOC1=CC=CC=C1 DLRJIFUOBPOJNS-UHFFFAOYSA-N 0.000 description 1
- QRUSAMIBASLVND-UHFFFAOYSA-N phenyl n,n-dichlorocarbamate Chemical compound ClN(Cl)C(=O)OC1=CC=CC=C1 QRUSAMIBASLVND-UHFFFAOYSA-N 0.000 description 1
- WXVSGQIVJIHVKH-UHFFFAOYSA-N phenyl n-chloro-n-phenylcarbamate Chemical compound C=1C=CC=CC=1N(Cl)C(=O)OC1=CC=CC=C1 WXVSGQIVJIHVKH-UHFFFAOYSA-N 0.000 description 1
- LAIWRIKKCCMYIX-UHFFFAOYSA-N phenyl n-chloro-n-propylcarbamate Chemical compound CCCN(Cl)C(=O)OC1=CC=CC=C1 LAIWRIKKCCMYIX-UHFFFAOYSA-N 0.000 description 1
- FJVNNOMOBHNDRT-UHFFFAOYSA-N phenyl n-chlorocarbamate Chemical compound ClNC(=O)OC1=CC=CC=C1 FJVNNOMOBHNDRT-UHFFFAOYSA-N 0.000 description 1
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- CYAFWKWGHFXITJ-UHFFFAOYSA-N propan-2-yl n-chloro-n-(4-methylphenyl)carbamate Chemical compound CC(C)OC(=O)N(Cl)C1=CC=C(C)C=C1 CYAFWKWGHFXITJ-UHFFFAOYSA-N 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 230000008929 regeneration Effects 0.000 description 1
- 238000011069 regeneration method Methods 0.000 description 1
- 238000006798 ring closing metathesis reaction Methods 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 230000002522 swelling effect Effects 0.000 description 1
- ISXSCDLOGDJUNJ-UHFFFAOYSA-N tert-butyl prop-2-enoate Chemical compound CC(C)(C)OC(=O)C=C ISXSCDLOGDJUNJ-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- HEKQWIORQJRILW-UHFFFAOYSA-N tetrakis(prop-2-enyl) benzene-1,2,4,5-tetracarboxylate Chemical compound C=CCOC(=O)C1=CC(C(=O)OCC=C)=C(C(=O)OCC=C)C=C1C(=O)OCC=C HEKQWIORQJRILW-UHFFFAOYSA-N 0.000 description 1
- DLFVBJFMPXGRIB-UHFFFAOYSA-N thioacetamide Natural products CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 1
- LSJNBGSOIVSBBR-UHFFFAOYSA-N thionyl fluoride Chemical compound FS(F)=O LSJNBGSOIVSBBR-UHFFFAOYSA-N 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 150000003613 toluenes Chemical class 0.000 description 1
- 125000004385 trihaloalkyl group Chemical group 0.000 description 1
- FIQMHBFVRAXMOP-UHFFFAOYSA-N triphenylphosphane oxide Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)(=O)C1=CC=CC=C1 FIQMHBFVRAXMOP-UHFFFAOYSA-N 0.000 description 1
- 238000007039 two-step reaction Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D205/00—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom
- C07D205/02—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings
- C07D205/06—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D205/08—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with one oxygen atom directly attached in position 2, e.g. beta-lactams
- C07D205/09—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with one oxygen atom directly attached in position 2, e.g. beta-lactams with a sulfur atom directly attached in position 4
- C07D205/095—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with one oxygen atom directly attached in position 2, e.g. beta-lactams with a sulfur atom directly attached in position 4 and with a nitrogen atom directly attached in position 3
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D205/00—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom
- C07D205/02—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings
- C07D205/06—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D205/08—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with one oxygen atom directly attached in position 2, e.g. beta-lactams
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Cephalosporin Compounds (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US96034778A | 1978-11-13 | 1978-11-13 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5566558A JPS5566558A (en) | 1980-05-20 |
| JPS641469B2 true JPS641469B2 (xx) | 1989-01-11 |
Family
ID=25503072
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP13278379A Granted JPS5566558A (en) | 1978-11-13 | 1979-10-12 | Manufacture of 22chlorosulfinylazetidinones |
Country Status (8)
| Country | Link |
|---|---|
| JP (1) | JPS5566558A (xx) |
| KR (1) | KR830001346B1 (xx) |
| BE (1) | BE879211A (xx) |
| CS (1) | CS209825B2 (xx) |
| MA (1) | MA18604A1 (xx) |
| MW (1) | MW3079A1 (xx) |
| ZA (1) | ZA795243B (xx) |
| ZM (1) | ZM8279A1 (xx) |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA1069126A (en) * | 1974-12-24 | 1980-01-01 | Eli Lilly And Company | Sulfinyl halides and their preparation from penicillin sulfoxides |
-
1979
- 1979-10-02 MA MA18804A patent/MA18604A1/fr unknown
- 1979-10-02 ZA ZA00795243A patent/ZA795243B/xx unknown
- 1979-10-05 BE BE1/9552A patent/BE879211A/fr not_active IP Right Cessation
- 1979-10-05 MW MW30/79A patent/MW3079A1/xx unknown
- 1979-10-09 ZM ZM82/79A patent/ZM8279A1/xx unknown
- 1979-10-12 CS CS796950A patent/CS209825B2/cs unknown
- 1979-10-12 JP JP13278379A patent/JPS5566558A/ja active Granted
- 1979-10-13 KR KR1019790003525A patent/KR830001346B1/ko active
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5566558A (en) | 1980-05-20 |
| MW3079A1 (en) | 1981-04-08 |
| CS209825B2 (en) | 1981-12-31 |
| BE879211A (fr) | 1980-04-08 |
| KR830001202A (ko) | 1983-04-29 |
| MA18604A1 (fr) | 1980-07-01 |
| ZA795243B (en) | 1981-05-27 |
| KR830001346B1 (ko) | 1983-07-14 |
| ZM8279A1 (en) | 1980-05-21 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US4289695A (en) | Process for preparing 2-chlorosulfinylazetidinones | |
| US4165315A (en) | Sulfinyl halides and their preparation from penicillin sulfoxides | |
| US4075203A (en) | Process for preparing a 3-exomethylenecepham sulfoxide from penicillin sulfoxides | |
| JPS641469B2 (xx) | ||
| US4165316A (en) | Process for preparing sulfinyl chlorides from penicillin sulfoxides | |
| KR20050010046A (ko) | 4'-브로모메틸-2-시아노비페닐의 제조방법 | |
| JPH0127075B2 (xx) | ||
| JPH0733715A (ja) | 炭酸エステルの製造方法 | |
| EP0015345B1 (en) | Process for preparing n-chloroimides | |
| US5070195A (en) | Ring-opening process for preparation of 2-chlorosulfinyl azetidinones | |
| US5347000A (en) | Process for the preparation of 2-chlorosulfinylazetidinone | |
| JPH0588210B2 (xx) | ||
| JP3010884B2 (ja) | シュウ酸ジアミド類の製造方法 | |
| JPH0261472B2 (xx) | ||
| SU1244144A1 (ru) | Способ очистки водного раствора капролактама | |
| JP3240786B2 (ja) | キノロンカルボン酸類の製造方法 | |
| IE42189B1 (en) | Sulfinyl halides and their preparation from penicillin sulfoxides | |
| JPH02193969A (ja) | テトラヒドロイソキノリン―３―カルボン酸の製造方法 | |
| EP0659742A1 (en) | An improved method for the preparation of 2-chloro sulfinyl azetidin-4-one | |
| JPH02193967A (ja) | ピリジン回収方法 | |
| JPH07109245A (ja) | ４，５−ジクロロフタル酸又はその塩の製造方法 | |
| JPH06100528A (ja) | ４，４’−ビス（４−メタクリロイルチオフェニル）スルフィドの製造方法 | |
| JPS6312463B2 (xx) | ||
| JPH06234675A (ja) | シリルエーテル化合物のシリル基の除去方法 | |
| JPS62441A (ja) | ナフトエ酸誘導体 |