NO762117L - - Google Patents
Info
- Publication number
- NO762117L NO762117L NO762117A NO762117A NO762117L NO 762117 L NO762117 L NO 762117L NO 762117 A NO762117 A NO 762117A NO 762117 A NO762117 A NO 762117A NO 762117 L NO762117 L NO 762117L
- Authority
- NO
- Norway
- Prior art keywords
- pentachlorophenyl
- group
- general formula
- mol
- salt
- Prior art date
Links
- -1 p-nitro-phenacyl Chemical group 0.000 claims description 78
- IZUPBVBPLAPZRR-UHFFFAOYSA-N pentachlorophenol Chemical compound OC1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl IZUPBVBPLAPZRR-UHFFFAOYSA-N 0.000 claims description 54
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 40
- 150000001875 compounds Chemical class 0.000 claims description 24
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 claims description 22
- 238000000034 method Methods 0.000 claims description 16
- 150000003839 salts Chemical class 0.000 claims description 15
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical class OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 14
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 9
- 239000002253 acid Substances 0.000 claims description 9
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 claims description 8
- 125000005843 halogen group Chemical group 0.000 claims description 7
- 239000007858 starting material Substances 0.000 claims description 7
- 150000004820 halides Chemical class 0.000 claims description 6
- WWYDYZMNFQIYPT-UHFFFAOYSA-N ru78191 Chemical group OC(=O)C(C(O)=O)C1=CC=CC=C1 WWYDYZMNFQIYPT-UHFFFAOYSA-N 0.000 claims description 6
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 125000000623 heterocyclic group Chemical group 0.000 claims description 4
- PEHSSTUGJUBZBI-UHFFFAOYSA-N indan-5-ol Chemical compound OC1=CC=C2CCCC2=C1 PEHSSTUGJUBZBI-UHFFFAOYSA-N 0.000 claims description 4
- 150000002690 malonic acid derivatives Chemical class 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- ZULZULTWAXZZFY-UHFFFAOYSA-N 2-(2,3,4,5,6-pentachlorophenyl)-2-(2-phenylphenyl)propanedioic acid Chemical compound C1=CC=C(C=C1)C2=CC=CC=C2C(C3=C(C(=C(C(=C3Cl)Cl)Cl)Cl)Cl)(C(=O)O)C(=O)O ZULZULTWAXZZFY-UHFFFAOYSA-N 0.000 claims description 2
- JKTYGPATCNUWKN-UHFFFAOYSA-N 4-nitrobenzyl alcohol Chemical compound OCC1=CC=C([N+]([O-])=O)C=C1 JKTYGPATCNUWKN-UHFFFAOYSA-N 0.000 claims description 2
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 2
- 125000004122 cyclic group Chemical group 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 2
- 125000002541 furyl group Chemical group 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims description 2
- 229910052740 iodine Inorganic materials 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 150000002989 phenols Chemical class 0.000 claims description 2
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 125000004076 pyridyl group Chemical group 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- 150000007513 acids Chemical class 0.000 claims 2
- 239000003960 organic solvent Substances 0.000 claims 2
- NYSXWUPVOCFRSE-UHFFFAOYSA-N 1-phenyl-ethene-1,2-diol Natural products OC=C(O)C1=CC=CC=C1 NYSXWUPVOCFRSE-UHFFFAOYSA-N 0.000 claims 1
- KPWDGTGXUYRARH-UHFFFAOYSA-N 2,2,2-trichloroethanol Chemical compound OCC(Cl)(Cl)Cl KPWDGTGXUYRARH-UHFFFAOYSA-N 0.000 claims 1
- FZHBPKVEPKLLFP-UHFFFAOYSA-N 2-(2,3,4,5,6-pentachloronaphthalen-1-yl)-2-(2-phenylphenyl)propanedioic acid Chemical compound C1=CC=C(C=C1)C2=CC=CC=C2C(C3=C(C(=C(C4=C3C=CC(=C4Cl)Cl)Cl)Cl)Cl)(C(=O)O)C(=O)O FZHBPKVEPKLLFP-UHFFFAOYSA-N 0.000 claims 1
- WLNGJWNIPAEMNH-UHFFFAOYSA-N 2-(4-nitro-2-phenylphenyl)-2-[2-oxo-2-(2,3,4,5,6-pentachlorophenyl)ethyl]propanedioic acid Chemical compound C1=CC=C(C=C1)C2=C(C=CC(=C2)[N+](=O)[O-])C(CC(=O)C3=C(C(=C(C(=C3Cl)Cl)Cl)Cl)Cl)(C(=O)O)C(=O)O WLNGJWNIPAEMNH-UHFFFAOYSA-N 0.000 claims 1
- HUMZBRDJXOEKIG-UHFFFAOYSA-N 2-[(2,3,4,5,6-pentachlorophenyl)methyl]-2-(2-phenylphenyl)propanedioic acid Chemical compound C1=CC=C(C=C1)C2=CC=CC=C2C(CC3=C(C(=C(C(=C3Cl)Cl)Cl)Cl)Cl)(C(=O)O)C(=O)O HUMZBRDJXOEKIG-UHFFFAOYSA-N 0.000 claims 1
- AWJSDXYIRPXSPG-UHFFFAOYSA-N 2-[2-oxo-2-(2,3,4,5,6-pentachlorophenyl)ethyl]-2-(2-phenylphenyl)propanedioic acid Chemical compound C1=CC=C(C=C1)C2=CC=CC=C2C(CC(=O)C3=C(C(=C(C(=C3Cl)Cl)Cl)Cl)Cl)(C(=O)O)C(=O)O AWJSDXYIRPXSPG-UHFFFAOYSA-N 0.000 claims 1
- ZWVHTXAYIKBMEE-UHFFFAOYSA-N 2-hydroxyacetophenone Chemical compound OCC(=O)C1=CC=CC=C1 ZWVHTXAYIKBMEE-UHFFFAOYSA-N 0.000 claims 1
- WWYDYZMNFQIYPT-UHFFFAOYSA-L 2-phenylpropanedioate Chemical compound [O-]C(=O)C(C([O-])=O)C1=CC=CC=C1 WWYDYZMNFQIYPT-UHFFFAOYSA-L 0.000 claims 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims 1
- OALPQLWZERYILY-UHFFFAOYSA-N C1CC2=CC=CC=C2C1C3=CC(=CC=C3)C(C4=C(C(=C(C(=C4Cl)Cl)Cl)Cl)Cl)(C(=O)O)C(=O)O Chemical compound C1CC2=CC=CC=C2C1C3=CC(=CC=C3)C(C4=C(C(=C(C(=C4Cl)Cl)Cl)Cl)Cl)(C(=O)O)C(=O)O OALPQLWZERYILY-UHFFFAOYSA-N 0.000 claims 1
- FGYDHYCFHBSNPE-UHFFFAOYSA-N diethyl phenylmalonate Chemical compound CCOC(=O)C(C(=O)OCC)C1=CC=CC=C1 FGYDHYCFHBSNPE-UHFFFAOYSA-N 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- XIWBCMGFBNMOMY-UHFFFAOYSA-N methyl(phenyl)malonic acid Chemical compound OC(=O)C(C)(C(O)=O)C1=CC=CC=C1 XIWBCMGFBNMOMY-UHFFFAOYSA-N 0.000 claims 1
- 125000001544 thienyl group Chemical group 0.000 claims 1
- 150000003739 xylenols Chemical class 0.000 claims 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 63
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 58
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 48
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 30
- 150000002148 esters Chemical class 0.000 description 29
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 21
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 16
- 239000000203 mixture Substances 0.000 description 15
- 230000009102 absorption Effects 0.000 description 14
- 238000010521 absorption reaction Methods 0.000 description 14
- XVMSFILGAMDHEY-UHFFFAOYSA-N 6-(4-aminophenyl)sulfonylpyridin-3-amine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=N1 XVMSFILGAMDHEY-UHFFFAOYSA-N 0.000 description 13
- 239000002904 solvent Substances 0.000 description 11
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 10
- 239000007787 solid Substances 0.000 description 10
- 239000000460 chlorine Substances 0.000 description 8
- 238000000921 elemental analysis Methods 0.000 description 8
- 238000004458 analytical method Methods 0.000 description 7
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 7
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 5
- 239000003795 chemical substances by application Substances 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 4
- OFOBLEOULBTSOW-UHFFFAOYSA-L Malonate Chemical compound [O-]C(=O)CC([O-])=O OFOBLEOULBTSOW-UHFFFAOYSA-L 0.000 description 4
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 4
- 230000002140 halogenating effect Effects 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 238000005917 acylation reaction Methods 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 3
- 150000002367 halogens Chemical group 0.000 description 3
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 3
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 230000010933 acylation Effects 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 230000003247 decreasing effect Effects 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 230000032050 esterification Effects 0.000 description 2
- 238000005886 esterification reaction Methods 0.000 description 2
- CCGKOQOJPYTBIH-UHFFFAOYSA-N ethenone Chemical compound C=C=O CCGKOQOJPYTBIH-UHFFFAOYSA-N 0.000 description 2
- BGMIRDHBNWQSGE-UHFFFAOYSA-N hypochlorous acid;pyridine Chemical compound ClO.C1=CC=NC=C1 BGMIRDHBNWQSGE-UHFFFAOYSA-N 0.000 description 2
- 150000002691 malonic acids Chemical class 0.000 description 2
- 150000003141 primary amines Chemical class 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 description 1
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- ADFXKUOMJKEIND-UHFFFAOYSA-N 1,3-dicyclohexylurea Chemical compound C1CCCCC1NC(=O)NC1CCCCC1 ADFXKUOMJKEIND-UHFFFAOYSA-N 0.000 description 1
- DUKLUIAXHKCMQI-UHFFFAOYSA-N 2,2-dichloropropanedioic acid Chemical class OC(=O)C(Cl)(Cl)C(O)=O DUKLUIAXHKCMQI-UHFFFAOYSA-N 0.000 description 1
- FWKCXFPQSXNCBW-UHFFFAOYSA-N 2,2-diethylpropanedioyl dichloride Chemical compound CCC(CC)(C(Cl)=O)C(Cl)=O FWKCXFPQSXNCBW-UHFFFAOYSA-N 0.000 description 1
- JAEJSNFTJMYIEF-UHFFFAOYSA-N 2-benzylpropanedioic acid Chemical compound OC(=O)C(C(O)=O)CC1=CC=CC=C1 JAEJSNFTJMYIEF-UHFFFAOYSA-N 0.000 description 1
- KPPZMQVVJYLLJL-UHFFFAOYSA-N 2-iodopropanedioic acid Chemical class OC(=O)C(I)C(O)=O KPPZMQVVJYLLJL-UHFFFAOYSA-N 0.000 description 1
- 125000002862 3,4-xylenyl group Chemical group [H]C1=C(O*)C([H])=C(C(=C1[H])C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- JSOGYDALMCJGDM-UHFFFAOYSA-N 3-(2,4-dimethylphenoxy)-3-oxo-2-phenylpropanoic acid Chemical compound CC1=CC(C)=CC=C1OC(=O)C(C(O)=O)C1=CC=CC=C1 JSOGYDALMCJGDM-UHFFFAOYSA-N 0.000 description 1
- INQWZSLKTMTMSK-UHFFFAOYSA-N 3-ethoxy-3-oxo-2-phenylpropanoic acid Chemical compound CCOC(=O)C(C(O)=O)C1=CC=CC=C1 INQWZSLKTMTMSK-UHFFFAOYSA-N 0.000 description 1
- 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 description 1
- CGRCONJBUOJMMZ-UHFFFAOYSA-N 3-oxo-2-(2,3,4,5,6-pentachlorophenyl)-2-phenyl-3-phenylmethoxypropanoic acid Chemical compound C(C1=CC=CC=C1)OC(C(C(=O)O)(C1=C(C(=C(C(=C1Cl)Cl)Cl)Cl)Cl)C1=CC=CC=C1)=O CGRCONJBUOJMMZ-UHFFFAOYSA-N 0.000 description 1
- QSBAHMROFICXDC-UHFFFAOYSA-N 3-oxo-2-phenyl-3-phenylmethoxypropanoic acid Chemical compound C=1C=CC=CC=1C(C(=O)O)C(=O)OCC1=CC=CC=C1 QSBAHMROFICXDC-UHFFFAOYSA-N 0.000 description 1
- IDJNJFYWPMDFNB-UHFFFAOYSA-N 3-oxo-3-phenoxy-2-phenylpropanoic acid Chemical compound C=1C=CC=CC=1C(C(=O)O)C(=O)OC1=CC=CC=C1 IDJNJFYWPMDFNB-UHFFFAOYSA-N 0.000 description 1
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 1
- NGHVIOIJCVXTGV-UHFFFAOYSA-N 6beta-amino-penicillanic acid Natural products OC(=O)C1C(C)(C)SC2C(N)C(=O)N21 NGHVIOIJCVXTGV-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- ZDZVKPXKLLLOOA-UHFFFAOYSA-N Allylmalonic acid Chemical compound OC(=O)C(C(O)=O)CC=C ZDZVKPXKLLLOOA-UHFFFAOYSA-N 0.000 description 1
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 230000006181 N-acylation Effects 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 230000006179 O-acylation Effects 0.000 description 1
- 239000006096 absorbing agent Substances 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 150000001782 cephems Chemical group 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- RCJVRSBWZCNNQT-UHFFFAOYSA-N dichloridooxygen Chemical compound ClOCl RCJVRSBWZCNNQT-UHFFFAOYSA-N 0.000 description 1
- 239000012738 dissolution medium Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 150000002085 enols Chemical class 0.000 description 1
- UKFXDFUAPNAMPJ-UHFFFAOYSA-N ethylmalonic acid Chemical compound CCC(C(O)=O)C(O)=O UKFXDFUAPNAMPJ-UHFFFAOYSA-N 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 150000002561 ketenes Chemical class 0.000 description 1
- CGJMROBVSBIBKP-UHFFFAOYSA-N malonamic acid Chemical class NC(=O)CC(O)=O CGJMROBVSBIBKP-UHFFFAOYSA-N 0.000 description 1
- 125000000346 malonyl group Chemical group C(CC(=O)*)(=O)* 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000012299 nitrogen atmosphere 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
- WSHJJCPTKWSMRR-RXMQYKEDSA-N penam Chemical compound S1CCN2C(=O)C[C@H]21 WSHJJCPTKWSMRR-RXMQYKEDSA-N 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000001384 succinic acid Substances 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 230000007306 turnover Effects 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D307/54—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/34—Esters of acyclic saturated polycarboxylic acids having an esterified carboxyl group bound to an acyclic carbon atom
- C07C69/38—Malonic acid esters
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyridine Compounds (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
- Furan Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU75CI00001592A HU171729B (hu) | 1975-06-20 | 1975-06-20 | Sposob poluchenija slozhnykh pentagalogenofenil-ehfirov malonovoj kisloty |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO762117L true NO762117L (es) | 1976-12-21 |
Family
ID=10994572
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO762117A NO762117L (es) | 1975-06-20 | 1976-06-18 |
Country Status (27)
| Country | Link |
|---|---|
| US (2) | US4324903A (es) |
| JP (1) | JPS5214736A (es) |
| AR (1) | AR219282A1 (es) |
| AT (1) | AT347924B (es) |
| AU (1) | AU509007B2 (es) |
| BE (1) | BE843106A (es) |
| BG (1) | BG24945A3 (es) |
| CA (1) | CA1080716A (es) |
| CH (1) | CH625778A5 (es) |
| CS (1) | CS191977B2 (es) |
| DD (1) | DD124725A5 (es) |
| DE (1) | DE2627709C2 (es) |
| DK (1) | DK155729C (es) |
| ES (1) | ES448967A1 (es) |
| FI (1) | FI761773A (es) |
| FR (1) | FR2316212A1 (es) |
| GB (1) | GB1546147A (es) |
| GR (1) | GR60049B (es) |
| HU (1) | HU171729B (es) |
| IL (1) | IL49808A0 (es) |
| IN (1) | IN144126B (es) |
| IT (1) | IT1078624B (es) |
| NL (1) | NL7606620A (es) |
| NO (1) | NO762117L (es) |
| PL (1) | PL103443B1 (es) |
| SE (1) | SE433607B (es) |
| SU (1) | SU691078A3 (es) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| HU179000B (en) * | 1977-07-13 | 1982-07-28 | Chinoin Gyogyszer Es Vegyeszet | Process for preparing new malonic acid esters |
| US6288879B1 (en) * | 1998-09-25 | 2001-09-11 | Seagate Technolocy Llc | Top down assembly of a disk drive actuator using a tolerance ring and a post |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2419865A (en) * | 1944-07-31 | 1947-04-29 | Abbott Lab | Carbalkoxylation of phenylacetates |
| GB1199249A (en) * | 1968-09-20 | 1970-07-15 | Pfizer & Co C | Direct Mono-Esterification of Aryl Malonic Acids |
| US3824275A (en) * | 1969-01-23 | 1974-07-16 | Pfizer | Direct mono-esterification of arylmalonic acids |
| BE747295A (fr) * | 1970-03-13 | 1970-09-14 | Pfizer | Monoesterification directe d'acides arylmaloniques |
-
1975
- 1975-06-20 HU HU75CI00001592A patent/HU171729B/hu not_active IP Right Cessation
-
1976
- 1976-06-12 GR GR50981A patent/GR60049B/el unknown
- 1976-06-15 BG BG7600033484A patent/BG24945A3/xx unknown
- 1976-06-16 IT IT68479/76A patent/IT1078624B/it active
- 1976-06-16 GB GB24999/76A patent/GB1546147A/en not_active Expired
- 1976-06-16 IN IN1057/CAL/76A patent/IN144126B/en unknown
- 1976-06-16 ES ES448967A patent/ES448967A1/es not_active Expired
- 1976-06-16 AT AT439176A patent/AT347924B/de not_active IP Right Cessation
- 1976-06-16 IL IL49808A patent/IL49808A0/xx unknown
- 1976-06-17 DD DD193413A patent/DD124725A5/xx unknown
- 1976-06-17 FR FR7618418A patent/FR2316212A1/fr active Granted
- 1976-06-18 CA CA255,260A patent/CA1080716A/en not_active Expired
- 1976-06-18 FI FI761773A patent/FI761773A/fi not_active Application Discontinuation
- 1976-06-18 AR AR263665A patent/AR219282A1/es active
- 1976-06-18 NL NL7606620A patent/NL7606620A/xx not_active Application Discontinuation
- 1976-06-18 CS CS764032A patent/CS191977B2/cs unknown
- 1976-06-18 SE SE7607044A patent/SE433607B/xx not_active IP Right Cessation
- 1976-06-18 NO NO762117A patent/NO762117L/no unknown
- 1976-06-18 JP JP51071301A patent/JPS5214736A/ja active Pending
- 1976-06-18 BE BE168053A patent/BE843106A/xx not_active IP Right Cessation
- 1976-06-18 SU SU762373644A patent/SU691078A3/ru active
- 1976-06-18 CH CH783476A patent/CH625778A5/de not_active IP Right Cessation
- 1976-06-18 DK DK273576A patent/DK155729C/da not_active IP Right Cessation
- 1976-06-18 AU AU15033/76A patent/AU509007B2/en not_active Expired
- 1976-06-19 PL PL1976190557A patent/PL103443B1/pl unknown
- 1976-06-21 US US05/698,063 patent/US4324903A/en not_active Expired - Lifetime
- 1976-06-21 DE DE2627709A patent/DE2627709C2/de not_active Expired
-
1979
- 1979-03-06 US US06/017,835 patent/US4289894A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| IT1078624B (it) | 1985-05-08 |
| FI761773A (es) | 1976-12-21 |
| BG24945A3 (en) | 1978-06-15 |
| DK155729B (da) | 1989-05-08 |
| AR219282A1 (es) | 1980-08-15 |
| US4289894A (en) | 1981-09-15 |
| US4324903A (en) | 1982-04-13 |
| AU509007B2 (en) | 1980-04-17 |
| ES448967A1 (es) | 1977-11-16 |
| AU1503376A (en) | 1977-12-22 |
| BE843106A (fr) | 1976-10-18 |
| PL103443B1 (pl) | 1979-06-30 |
| NL7606620A (nl) | 1976-12-22 |
| GR60049B (en) | 1978-04-01 |
| DK155729C (da) | 1989-10-16 |
| CS191977B2 (en) | 1979-07-31 |
| GB1546147A (en) | 1979-05-16 |
| IN144126B (es) | 1978-03-25 |
| DE2627709C2 (de) | 1983-01-05 |
| ATA439176A (de) | 1978-06-15 |
| FR2316212B1 (es) | 1980-01-25 |
| SE7607044L (sv) | 1976-12-21 |
| DD124725A5 (es) | 1977-03-09 |
| SU691078A3 (ru) | 1979-10-05 |
| AT347924B (de) | 1979-01-25 |
| IL49808A0 (en) | 1976-08-31 |
| CA1080716A (en) | 1980-07-01 |
| HU171729B (hu) | 1978-03-28 |
| DK273576A (da) | 1976-12-21 |
| SE433607B (sv) | 1984-06-04 |
| DE2627709A1 (de) | 1976-12-30 |
| FR2316212A1 (fr) | 1977-01-28 |
| JPS5214736A (en) | 1977-02-03 |
| CH625778A5 (es) | 1981-10-15 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JPH0733729A (ja) | Ｎ−シアノ−ｎ′−置換−アリールカルボキシイミダミド化合物の製造法 | |
| NO762117L (es) | ||
| US3910958A (en) | Process for preparing arylacetic acids and esters thereof | |
| KR20190049883A (ko) | 페닐알라닌 화합물의 제조 방법 | |
| JPS595595B2 (ja) | １５−ヒドロキシイミノ−ｅ−ホモエブルナン誘導体の製造方法 | |
| US4182892A (en) | Malonic esters | |
| EP0006864B1 (en) | A novel intermediate to prepare therapeutically active pyridine compounds and process for its preparation | |
| DK156221B (da) | Fremgangsmaade til fremstilling af penicillansyre- og cephalosporansyrederivater | |
| US3824251A (en) | Complex compound of a substituted 3-amino-3-pyrazolin-5-one and methods of producing and further reacting the same | |
| JPH09132554A (ja) | ４−アルコキシ−１，１，１−トリフルオロ−３−ブテン−２−オンの製造方法 | |
| US4010178A (en) | Carbonic acid esters, and the preparation thereof and their use | |
| JPS5888361A (ja) | ３−アミノ−１，４−ビス（アルコキシカルボニル）マレイミド類およびその製法 | |
| JP2000053648A (ja) | カルボキシアミドオキシムの精製方法 | |
| HU201516B (en) | Process for producing 2-cyano-2-oximinoacetamide derivatives | |
| US2517588A (en) | Process for manufacture of penaldic acids and their derivatives | |
| SU1483875A1 (ru) | Способ получени 1-(ацилокси)-алкильных четвертичных аммониевых солей | |
| SU1087518A1 (ru) | Способ получени @ , @ -метилен-бис-( @ -винилсульфонилпропионамида) | |
| KR0142140B1 (ko) | 2-벤조일-3-아미노아크릴레이트 유도체의 제조방법 | |
| JPH0789924A (ja) | カルバマート類の製造法 | |
| JPH0665180A (ja) | ベンゾイルアセトニトリル誘導体及びその製造方法 | |
| JPH02304090A (ja) | 多環式化合物の製造方法 | |
| JP2963724B2 (ja) | ピロール―２―カルボン酸の製造法 | |
| JP3011784B2 (ja) | 新規なピリジンスルホン酸エステル | |
| JP2005263748A (ja) | 反応性ジアジリン基を有するホモフェニルアラニン誘導体 | |
| JPH0759557B2 (ja) | １，３−ジアルキルピラゾール−４−アルデヒド誘導体の製造方法 |