LU82119A1 - Reactifs d'halogenation phosphite de triaryle/halogene et leur procede de preparation - Google Patents
Reactifs d'halogenation phosphite de triaryle/halogene et leur procede de preparation Download PDFInfo
- Publication number
- LU82119A1 LU82119A1 LU82119A LU82119A LU82119A1 LU 82119 A1 LU82119 A1 LU 82119A1 LU 82119 A LU82119 A LU 82119A LU 82119 A LU82119 A LU 82119A LU 82119 A1 LU82119 A1 LU 82119A1
- Authority
- LU
- Luxembourg
- Prior art keywords
- phosphite
- chlorine
- bromine
- triaryl
- reaction
- Prior art date
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- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 title claims description 61
- 230000026030 halogenation Effects 0.000 title claims description 22
- 238000005658 halogenation reaction Methods 0.000 title claims description 22
- 238000002360 preparation method Methods 0.000 title claims description 15
- 229910052736 halogen Inorganic materials 0.000 title description 19
- 150000002367 halogens Chemical class 0.000 title description 19
- 239000003153 chemical reaction reagent Substances 0.000 title description 15
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 99
- 239000000460 chlorine Substances 0.000 claims description 57
- 229910052801 chlorine Inorganic materials 0.000 claims description 53
- HVLLSGMXQDNUAL-UHFFFAOYSA-N triphenyl phosphite Chemical group C=1C=CC=CC=1OP(OC=1C=CC=CC=1)OC1=CC=CC=C1 HVLLSGMXQDNUAL-UHFFFAOYSA-N 0.000 claims description 49
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 47
- 150000001875 compounds Chemical class 0.000 claims description 34
- 238000006243 chemical reaction Methods 0.000 claims description 33
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 26
- 229910052794 bromium Inorganic materials 0.000 claims description 26
- 238000000034 method Methods 0.000 claims description 26
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 25
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 17
- 239000002904 solvent Substances 0.000 claims description 17
- 238000005481 NMR spectroscopy Methods 0.000 claims description 16
- 239000003960 organic solvent Substances 0.000 claims description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 9
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 8
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 6
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 6
- BKHZQJRTFNFCTG-UHFFFAOYSA-N tris(2-methylphenyl) phosphite Chemical group CC1=CC=CC=C1OP(OC=1C(=CC=CC=1)C)OC1=CC=CC=C1C BKHZQJRTFNFCTG-UHFFFAOYSA-N 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 150000008282 halocarbons Chemical class 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- VFWCMGCRMGJXDK-UHFFFAOYSA-N 1-chlorobutane Chemical compound CCCCCl VFWCMGCRMGJXDK-UHFFFAOYSA-N 0.000 claims description 2
- 230000033228 biological regulation Effects 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 2
- XZZNDPSIHUTMOC-UHFFFAOYSA-N triphenyl phosphate Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)(=O)OC1=CC=CC=C1 XZZNDPSIHUTMOC-UHFFFAOYSA-N 0.000 claims 2
- 230000009102 absorption Effects 0.000 claims 1
- 238000010521 absorption reaction Methods 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 claims 1
- 125000001246 bromo group Chemical group Br* 0.000 claims 1
- 238000002329 infrared spectrum Methods 0.000 claims 1
- 239000000047 product Substances 0.000 description 63
- 239000000243 solution Substances 0.000 description 48
- 239000011541 reaction mixture Substances 0.000 description 40
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 18
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 16
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
- -1 -halo 3-cephem derivatives Chemical class 0.000 description 12
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- 239000003795 chemical substances by application Substances 0.000 description 11
- 238000000354 decomposition reaction Methods 0.000 description 11
- 239000000203 mixture Substances 0.000 description 11
- 238000003756 stirring Methods 0.000 description 11
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 230000002140 halogenating effect Effects 0.000 description 9
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 9
- 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 8
- 230000015572 biosynthetic process Effects 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 125000003118 aryl group Chemical group 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
- 239000007789 gas Substances 0.000 description 4
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 4
- AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 description 4
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- 239000000758 substrate Substances 0.000 description 4
- 150000003512 tertiary amines Chemical class 0.000 description 4
- 230000009466 transformation Effects 0.000 description 4
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 3
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 3
- 229930186147 Cephalosporin Natural products 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 229910019142 PO4 Inorganic materials 0.000 description 3
- 150000001336 alkenes Chemical class 0.000 description 3
- 230000005587 bubbling Effects 0.000 description 3
- 229940124587 cephalosporin Drugs 0.000 description 3
- 150000001780 cephalosporins Chemical class 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 230000014509 gene expression Effects 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 3
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 3
- 239000010452 phosphate Substances 0.000 description 3
- 229910052698 phosphorus Inorganic materials 0.000 description 3
- 125000006239 protecting group Chemical group 0.000 description 3
- ZUBXPSDFPQTKQN-ZCFIWIBFSA-N (6r)-3-hydroxy-5-thia-1-azabicyclo[4.2.0]oct-2-en-8-one Chemical class S1CC(O)=CN2C(=O)C[C@H]21 ZUBXPSDFPQTKQN-ZCFIWIBFSA-N 0.000 description 2
- UBOXGVDOUJQMTN-UHFFFAOYSA-N 1,1,2-trichloroethane Chemical compound ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 description 2
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 2
- BKOOMYPCSUNDGP-UHFFFAOYSA-N 2-methylbut-2-ene Chemical group CC=C(C)C BKOOMYPCSUNDGP-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
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- 125000001931 aliphatic group Chemical group 0.000 description 2
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- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 150000001925 cycloalkenes Chemical class 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 230000018109 developmental process Effects 0.000 description 1
- JSYGRUBHOCKMGQ-UHFFFAOYSA-N dichloramine Chemical compound ClNCl JSYGRUBHOCKMGQ-UHFFFAOYSA-N 0.000 description 1
- ASWXNYNXAOQCCD-UHFFFAOYSA-N dichloro(triphenyl)-$l^{5}-phosphane Chemical compound C=1C=CC=CC=1P(Cl)(C=1C=CC=CC=1)(Cl)C1=CC=CC=C1 ASWXNYNXAOQCCD-UHFFFAOYSA-N 0.000 description 1
- 229940117389 dichlorobenzene Drugs 0.000 description 1
- 150000001993 dienes Chemical class 0.000 description 1
- 150000002009 diols Chemical class 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 229960003750 ethyl chloride Drugs 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 125000002534 ethynyl group Chemical class [H]C#C* 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 230000008014 freezing Effects 0.000 description 1
- 238000007710 freezing Methods 0.000 description 1
- 230000006870 function Effects 0.000 description 1
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 1
- MNWFXJYAOYHMED-UHFFFAOYSA-M heptanoate Chemical compound CCCCCCC([O-])=O MNWFXJYAOYHMED-UHFFFAOYSA-M 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- ULYZAYCEDJDHCC-UHFFFAOYSA-N isopropyl chloride Chemical compound CC(C)Cl ULYZAYCEDJDHCC-UHFFFAOYSA-N 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- AUHZEENZYGFFBQ-UHFFFAOYSA-N mesitylene Substances CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 description 1
- 125000001827 mesitylenyl group Chemical group [H]C1=C(C(*)=C(C([H])=C1C([H])([H])[H])C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 1
- PYLWMHQQBFSUBP-UHFFFAOYSA-N monofluorobenzene Chemical compound FC1=CC=CC=C1 PYLWMHQQBFSUBP-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- UUIQMZJEGPQKFD-UHFFFAOYSA-N n-butyric acid methyl ester Natural products CCCC(=O)OC UUIQMZJEGPQKFD-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
- 150000002825 nitriles Chemical class 0.000 description 1
- 150000002828 nitro derivatives Chemical class 0.000 description 1
- 125000006502 nitrobenzyl group Chemical group 0.000 description 1
- MCSAJNNLRCFZED-UHFFFAOYSA-N nitroethane Chemical compound CC[N+]([O-])=O MCSAJNNLRCFZED-UHFFFAOYSA-N 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 1
- 238000010899 nucleation Methods 0.000 description 1
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 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
- 150000002960 penicillins Chemical class 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- UXCDUFKZSUBXGM-UHFFFAOYSA-N phosphoric tribromide Chemical compound BrP(Br)(Br)=O UXCDUFKZSUBXGM-UHFFFAOYSA-N 0.000 description 1
- 150000003018 phosphorus compounds Chemical class 0.000 description 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 238000004321 preservation Methods 0.000 description 1
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 230000029305 taxis Effects 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- HFRXJVQOXRXOPP-UHFFFAOYSA-N thionyl bromide Chemical compound BrS(Br)=O HFRXJVQOXRXOPP-UHFFFAOYSA-N 0.000 description 1
- DBLLQROLCMTZJP-UHFFFAOYSA-N tris(2-methylphenyl) phosphite dihydrochloride Chemical compound Cl.Cl.CC1=CC=CC=C1OP(OC=1C(=CC=CC=1)C)OC1=CC=CC=C1C DBLLQROLCMTZJP-UHFFFAOYSA-N 0.000 description 1
- AZLGDNBTDKZORI-UHFFFAOYSA-N tris(3-methylphenyl) phosphite Chemical compound CC1=CC=CC(OP(OC=2C=C(C)C=CC=2)OC=2C=C(C)C=CC=2)=C1 AZLGDNBTDKZORI-UHFFFAOYSA-N 0.000 description 1
- DFQHFXCKNSCDFW-UHFFFAOYSA-N tris(4-chlorophenyl) phosphate Chemical compound C1=CC(Cl)=CC=C1OP(=O)(OC=1C=CC(Cl)=CC=1)OC1=CC=C(Cl)C=C1 DFQHFXCKNSCDFW-UHFFFAOYSA-N 0.000 description 1
- AMGMFFUMIJRDGW-UHFFFAOYSA-N tris(4-chlorophenyl) phosphite Chemical compound C1=CC(Cl)=CC=C1OP(OC=1C=CC(Cl)=CC=1)OC1=CC=C(Cl)C=C1 AMGMFFUMIJRDGW-UHFFFAOYSA-N 0.000 description 1
- ONPCEUYAHKMPDV-UHFFFAOYSA-N tris(4-propan-2-yloxyphenyl) phosphite Chemical compound C1=CC(OC(C)C)=CC=C1OP(OC=1C=CC(OC(C)C)=CC=1)OC1=CC=C(OC(C)C)C=C1 ONPCEUYAHKMPDV-UHFFFAOYSA-N 0.000 description 1
- 238000001665 trituration Methods 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 150000003952 β-lactams Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/08—Esters of oxyacids of phosphorus
- C07F9/141—Esters of phosphorous acids
- C07F9/146—Esters of phosphorous acids containing P-halide groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/08—Esters of oxyacids of phosphorus
- C07F9/141—Esters of phosphorous acids
- C07F9/145—Esters of phosphorous acids with hydroxyaryl compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/062—Organo-phosphoranes without P-C bonds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Biochemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Cephalosporin Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Manufacture Of Macromolecular Shaped Articles (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US06/008,469 US4230644A (en) | 1979-02-01 | 1979-02-01 | Halogenating reagents |
US846979 | 1979-02-01 |
Publications (1)
Publication Number | Publication Date |
---|---|
LU82119A1 true LU82119A1 (fr) | 1980-04-23 |
Family
ID=21731778
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
LU82119A LU82119A1 (fr) | 1979-02-01 | 1980-01-31 | Reactifs d'halogenation phosphite de triaryle/halogene et leur procede de preparation |
Country Status (42)
Country | Link |
---|---|
US (1) | US4230644A (de) |
EP (1) | EP0015079B1 (de) |
JP (1) | JPS55104291A (de) |
KR (1) | KR840000298B1 (de) |
AT (1) | AT386209B (de) |
AU (1) | AU532614B2 (de) |
BE (1) | BE881424A (de) |
BG (1) | BG34462A3 (de) |
CA (1) | CA1133007A (de) |
CH (1) | CH643855A5 (de) |
CS (1) | CS215128B2 (de) |
DD (1) | DD148954A1 (de) |
DE (1) | DE3072025D1 (de) |
DK (1) | DK147886C (de) |
ES (1) | ES488230A0 (de) |
FI (1) | FI72728C (de) |
FR (1) | FR2447928B1 (de) |
GB (1) | GB2044266B (de) |
GR (1) | GR71613B (de) |
GT (1) | GT198061668A (de) |
HK (1) | HK42088A (de) |
HU (1) | HU182094B (de) |
IE (1) | IE49505B1 (de) |
IL (1) | IL59267A (de) |
IT (1) | IT1212406B (de) |
LU (1) | LU82119A1 (de) |
MA (1) | MA18714A1 (de) |
MW (1) | MW680A1 (de) |
MX (1) | MX6199E (de) |
MY (2) | MY8500571A (de) |
NL (1) | NL192107C (de) |
NO (1) | NO161260C (de) |
NZ (1) | NZ192747A (de) |
OA (1) | OA06450A (de) |
PL (1) | PL120667B1 (de) |
PT (1) | PT70743A (de) |
RO (1) | RO79358A (de) |
SG (1) | SG3688G (de) |
SU (1) | SU982545A3 (de) |
YU (1) | YU22680A (de) |
ZA (1) | ZA80520B (de) |
ZM (1) | ZM1180A1 (de) |
Families Citing this family (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
IL93096A0 (en) * | 1989-01-23 | 1990-11-05 | Lilly Co Eli | Halogenation process |
CN103588790A (zh) * | 2013-11-29 | 2014-02-19 | 中国科学院长春应用化学研究所 | 7-氨基-3-氯-3-头孢-4-羧酸-对硝基苄基酯的制备方法 |
CN114591199B (zh) * | 2022-03-17 | 2024-03-12 | 诚弘制药(威海)有限责任公司 | 一种溴乙腈的制备方法 |
Family Cites Families (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3925372A (en) * | 1973-02-23 | 1975-12-09 | Lilly Co Eli | Alpha-aminoacyl-3-halo cephalosporins |
-
1979
- 1979-02-01 US US06/008,469 patent/US4230644A/en not_active Expired - Lifetime
-
1980
- 1980-01-29 GR GR61066A patent/GR71613B/el unknown
- 1980-01-29 ZA ZA00800520A patent/ZA80520B/xx unknown
- 1980-01-29 IL IL59267A patent/IL59267A/xx unknown
- 1980-01-29 YU YU00226/80A patent/YU22680A/xx unknown
- 1980-01-29 HU HU80191A patent/HU182094B/hu unknown
- 1980-01-29 AU AU55027/80A patent/AU532614B2/en not_active Expired
- 1980-01-29 PT PT70743A patent/PT70743A/pt active IP Right Revival
- 1980-01-29 NZ NZ192747A patent/NZ192747A/xx unknown
- 1980-01-29 MA MA18911A patent/MA18714A1/fr unknown
- 1980-01-29 NL NL8000544A patent/NL192107C/nl not_active IP Right Cessation
- 1980-01-30 FR FR8001967A patent/FR2447928B1/fr not_active Expired
- 1980-01-30 BE BE1/9700A patent/BE881424A/fr not_active IP Right Cessation
- 1980-01-30 GT GT198061668A patent/GT198061668A/es unknown
- 1980-01-30 CA CA344,681A patent/CA1133007A/en not_active Expired
- 1980-01-30 BG BG046410A patent/BG34462A3/xx unknown
- 1980-01-31 AT AT0050080A patent/AT386209B/de not_active IP Right Cessation
- 1980-01-31 DE DE8080300282T patent/DE3072025D1/de not_active Expired
- 1980-01-31 JP JP1196580A patent/JPS55104291A/ja active Granted
- 1980-01-31 CH CH79680A patent/CH643855A5/fr not_active IP Right Cessation
- 1980-01-31 IE IE189/80A patent/IE49505B1/en not_active IP Right Cessation
- 1980-01-31 EP EP80300282A patent/EP0015079B1/de not_active Expired
- 1980-01-31 DK DK41280A patent/DK147886C/da active
- 1980-01-31 LU LU82119A patent/LU82119A1/fr unknown
- 1980-01-31 IT IT8019608A patent/IT1212406B/it active
- 1980-01-31 GB GB8003292A patent/GB2044266B/en not_active Expired
- 1980-01-31 NO NO800250A patent/NO161260C/no unknown
- 1980-01-31 CS CS80659A patent/CS215128B2/cs unknown
- 1980-02-01 FI FI800302A patent/FI72728C/fi not_active IP Right Cessation
- 1980-02-01 SU SU802877706A patent/SU982545A3/ru active
- 1980-02-01 MW MW6/80A patent/MW680A1/xx unknown
- 1980-02-01 RO RO80100057A patent/RO79358A/ro unknown
- 1980-02-01 PL PL1980221746A patent/PL120667B1/pl unknown
- 1980-02-01 DD DD80218817A patent/DD148954A1/de unknown
- 1980-02-01 OA OA57010A patent/OA06450A/xx unknown
- 1980-02-01 MX MX808626U patent/MX6199E/es unknown
- 1980-02-01 KR KR1019800000399A patent/KR840000298B1/ko not_active IP Right Cessation
- 1980-02-01 ZM ZM11/80A patent/ZM1180A1/xx unknown
- 1980-02-01 ES ES488230A patent/ES488230A0/es active Granted
-
1985
- 1985-12-30 MY MY571/85A patent/MY8500571A/xx unknown
-
1987
- 1987-09-22 MY MYPI87001867A patent/MY102552A/en unknown
-
1988
- 1988-01-08 SG SG36/88A patent/SG3688G/en unknown
- 1988-06-02 HK HK420/88A patent/HK42088A/xx not_active IP Right Cessation
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