SU354655A1 - - Google Patents
Info
- Publication number
- SU354655A1 SU354655A1 SU1439004A SU1439004A SU354655A1 SU 354655 A1 SU354655 A1 SU 354655A1 SU 1439004 A SU1439004 A SU 1439004A SU 1439004 A SU1439004 A SU 1439004A SU 354655 A1 SU354655 A1 SU 354655A1
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- acid
- ester
- vacuo
- acetonitrile
- acetic acid
- Prior art date
Links
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 24
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 20
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
- -1 PHENYLIMIDAZOLYL Chemical class 0.000 description 14
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 9
- 239000002253 acid Substances 0.000 description 8
- 239000002904 solvent Substances 0.000 description 7
- 238000000034 method Methods 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 4
- 150000003254 radicals Chemical group 0.000 description 4
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- 229940053200 antiepileptics fatty acid derivative Drugs 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 239000004310 lactic acid Substances 0.000 description 2
- 235000014655 lactic acid Nutrition 0.000 description 2
- 150000004702 methyl esters Chemical class 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 2
- FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 2
- 229960004889 salicylic acid Drugs 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 1
- AVKUPUSZQPSBOD-UHFFFAOYSA-N 2-(1h-imidazol-2-yl)-2,2-diphenylacetic acid Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(C(=O)O)C1=NC=CN1 AVKUPUSZQPSBOD-UHFFFAOYSA-N 0.000 description 1
- PTKAGHMFWYFHBU-UHFFFAOYSA-N 2-(1h-imidazol-2-yl)-2,2-diphenylacetonitrile Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(C#N)C1=NC=CN1 PTKAGHMFWYFHBU-UHFFFAOYSA-N 0.000 description 1
- KPLPVBYRJKTRMQ-UHFFFAOYSA-N 2-(1h-imidazol-2-yl)-2-(2-methylphenyl)-2-phenylacetic acid Chemical compound CC1=CC=CC=C1C(C(O)=O)(C=1C=CC=CC=1)C1=NC=CN1 KPLPVBYRJKTRMQ-UHFFFAOYSA-N 0.000 description 1
- RLBXCQGSVGQNJA-UHFFFAOYSA-N 2-chloro-2,2-diphenylacetonitrile Chemical compound C=1C=CC=CC=1C(C#N)(Cl)C1=CC=CC=C1 RLBXCQGSVGQNJA-UHFFFAOYSA-N 0.000 description 1
- CGJVFUZUKVZYOB-UHFFFAOYSA-N 2-methylpropyl 2-chloro-2,2-diphenylacetate Chemical compound C=1C=CC=CC=1C(Cl)(C(=O)OCC(C)C)C1=CC=CC=C1 CGJVFUZUKVZYOB-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical compound SS BWGNESOTFCXPMA-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 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
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- HJNNMNQHFFMNKH-UHFFFAOYSA-N benzyl 2-(1h-imidazol-2-yl)-2,2-diphenylacetate Chemical group N=1C=CNC=1C(C=1C=CC=CC=1)(C=1C=CC=CC=1)C(=O)OCC1=CC=CC=C1 HJNNMNQHFFMNKH-UHFFFAOYSA-N 0.000 description 1
- CFGHWLWBJBVEJC-UHFFFAOYSA-N benzyl 2-chloro-2,2-diphenylacetate Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(Cl)C(=O)OCC1=CC=CC=C1 CFGHWLWBJBVEJC-UHFFFAOYSA-N 0.000 description 1
- 230000001588 bifunctional effect Effects 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- 125000005521 carbonamide group Chemical group 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- BEFDCLMNVWHSGT-UHFFFAOYSA-N ethenylcyclopentane Chemical compound C=CC1CCCC1 BEFDCLMNVWHSGT-UHFFFAOYSA-N 0.000 description 1
- IQDLKFJCEIJFGN-UHFFFAOYSA-N ethyl 2-(1h-imidazol-2-yl)-2,2-diphenylacetate Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(C(=O)OCC)C1=NC=CN1 IQDLKFJCEIJFGN-UHFFFAOYSA-N 0.000 description 1
- MCGGQYKHZGQEGN-UHFFFAOYSA-N ethyl 2-(4-chlorophenyl)-2-(1h-imidazol-2-yl)-2-phenylacetate Chemical compound C=1C=CC=CC=1C(C=1C=CC(Cl)=CC=1)(C(=O)OCC)C1=NC=CN1 MCGGQYKHZGQEGN-UHFFFAOYSA-N 0.000 description 1
- MSBGLMWCKRSNHW-UHFFFAOYSA-N ethyl 2-chloro-2,2-diphenylacetate Chemical compound C=1C=CC=CC=1C(Cl)(C(=O)OCC)C1=CC=CC=C1 MSBGLMWCKRSNHW-UHFFFAOYSA-N 0.000 description 1
- PDWBYRLVGPMRGN-UHFFFAOYSA-N ethyl 2-chloro-2-(4-chlorophenyl)-2-phenylacetate Chemical compound C=1C=C(Cl)C=CC=1C(Cl)(C(=O)OCC)C1=CC=CC=C1 PDWBYRLVGPMRGN-UHFFFAOYSA-N 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 150000002460 imidazoles Chemical class 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 239000001630 malic acid Substances 0.000 description 1
- 235000011090 malic acid Nutrition 0.000 description 1
- OMLSYNQYPRJYAR-UHFFFAOYSA-N methyl 2-(1h-imidazol-2-yl)-2,2-diphenylacetate Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(C(=O)OC)C1=NC=CN1 OMLSYNQYPRJYAR-UHFFFAOYSA-N 0.000 description 1
- ILVSUJHMWHCKOI-UHFFFAOYSA-N methyl 2-chloro-2,2-diphenylacetate Chemical compound C=1C=CC=CC=1C(Cl)(C(=O)OC)C1=CC=CC=C1 ILVSUJHMWHCKOI-UHFFFAOYSA-N 0.000 description 1
- ZFFYVOGDTWBQSG-UHFFFAOYSA-N methyl 2-chloro-2-(4-methylphenyl)-2-phenylacetate Chemical compound C=1C=C(C)C=CC=1C(Cl)(C(=O)OC)C1=CC=CC=C1 ZFFYVOGDTWBQSG-UHFFFAOYSA-N 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- PRRHXUDAIBCCOD-UHFFFAOYSA-N propyl 2-(1h-imidazol-2-yl)-2,2-diphenylacetate Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(C(=O)OCCC)C1=NC=CN1 PRRHXUDAIBCCOD-UHFFFAOYSA-N 0.000 description 1
- ZKSUJTQPJAGLCM-UHFFFAOYSA-N propyl 2-chloro-2,2-diphenylacetate Chemical compound C=1C=CC=CC=1C(Cl)(C(=O)OCCC)C1=CC=CC=C1 ZKSUJTQPJAGLCM-UHFFFAOYSA-N 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000004334 sorbic acid Substances 0.000 description 1
- 235000010199 sorbic acid Nutrition 0.000 description 1
- 229940075582 sorbic acid Drugs 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU354655A1 true SU354655A1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) |
Family
ID=
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