SU677656A3 - Способ получени оптически активных низших алкил 1-(1-фенилэтил)-1н-имидазол-5-карбоксилатов - Google Patents
Способ получени оптически активных низших алкил 1-(1-фенилэтил)-1н-имидазол-5-карбоксилатовInfo
- Publication number
- SU677656A3 SU677656A3 SU762329945A SU2329945A SU677656A3 SU 677656 A3 SU677656 A3 SU 677656A3 SU 762329945 A SU762329945 A SU 762329945A SU 2329945 A SU2329945 A SU 2329945A SU 677656 A3 SU677656 A3 SU 677656A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- phenylethyl
- imidazole
- optically active
- mixture
- naphthyl
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 4
- 150000003839 salts Chemical class 0.000 claims description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 9
- 125000004343 1-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C([H])([H])[H] 0.000 claims description 7
- RGYCCBLTSWHXIS-UHFFFAOYSA-N 3-(1-phenylethyl)imidazole-4-carboxylic acid Chemical compound C1=NC=C(C(O)=O)N1C(C)C1=CC=CC=C1 RGYCCBLTSWHXIS-UHFFFAOYSA-N 0.000 claims description 5
- -1 chloro anhydride Chemical class 0.000 claims description 5
- 239000002253 acid Substances 0.000 claims description 4
- VKAXROBZTQXXIH-UHFFFAOYSA-N 1-naphthalen-1-ylethanamine;1-phenylethanamine Chemical class CC(N)C1=CC=CC=C1.C1=CC=C2C(C(N)C)=CC=CC2=C1 VKAXROBZTQXXIH-UHFFFAOYSA-N 0.000 claims 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims 2
- KHSYYLCXQKCYQX-UHFFFAOYSA-N 1-naphthalen-2-ylethanamine Chemical class C1=CC=CC2=CC(C(N)C)=CC=C21 KHSYYLCXQKCYQX-UHFFFAOYSA-N 0.000 claims 1
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims 1
- 229910052500 inorganic mineral Inorganic materials 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 239000011707 mineral Substances 0.000 claims 1
- 239000003960 organic solvent Substances 0.000 claims 1
- 230000001590 oxidative effect Effects 0.000 claims 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 32
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 23
- 239000000203 mixture Substances 0.000 description 20
- 239000000047 product Substances 0.000 description 19
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
- 239000011541 reaction mixture Substances 0.000 description 11
- 235000011121 sodium hydroxide Nutrition 0.000 description 11
- 239000000284 extract Substances 0.000 description 9
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- 229960004592 isopropanol Drugs 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 6
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 5
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 5
- 238000001816 cooling Methods 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- NKWCGTOZTHZDHB-UHFFFAOYSA-N 1h-imidazol-1-ium-4-carboxylate Chemical compound OC(=O)C1=CNC=N1 NKWCGTOZTHZDHB-UHFFFAOYSA-N 0.000 description 3
- 229910002651 NO3 Inorganic materials 0.000 description 3
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 3
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 3
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 3
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 239000002480 mineral oil Substances 0.000 description 2
- 235000010446 mineral oil Nutrition 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- JMHMSRUKQIGVQC-UHFFFAOYSA-N 1-(1-phenylethyl)imidazole-2-carboxylic acid Chemical compound CC(C1=CC=CC=C1)N2C=CN=C2C(=O)O JMHMSRUKQIGVQC-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 1
- GVPLHNOLAZHXTL-UHFFFAOYSA-N O.S(=O)(=O)(O)O.C1(=CC=CC=C1)C(C)N1C=NC=C1C(=O)OCCC Chemical compound O.S(=O)(=O)(O)O.C1(=CC=CC=C1)C(C)N1C=NC=C1C(=O)OCCC GVPLHNOLAZHXTL-UHFFFAOYSA-N 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 239000012300 argon atmosphere Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- POLCUAVZOMRGSN-UHFFFAOYSA-N dipropyl ether Chemical compound CCCOCCC POLCUAVZOMRGSN-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- YCUUCSZGTWIJDW-UHFFFAOYSA-N ethyl 3-(1-phenylethyl)imidazole-4-carboxylate;sulfuric acid Chemical compound OS(O)(=O)=O.CCOC(=O)C1=CN=CN1C(C)C1=CC=CC=C1 YCUUCSZGTWIJDW-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- MDBBRPQAWWLQAY-UHFFFAOYSA-N methyl 3-(1-phenylethyl)imidazole-4-carboxylate;sulfuric acid Chemical compound OS(O)(=O)=O.COC(=O)C1=CN=CN1C(C)C1=CC=CC=C1 MDBBRPQAWWLQAY-UHFFFAOYSA-N 0.000 description 1
- 125000006178 methyl benzyl group Chemical group 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- TVDSBUOJIPERQY-UHFFFAOYSA-N prop-2-yn-1-ol Chemical compound OCC#C TVDSBUOJIPERQY-UHFFFAOYSA-N 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- GDSJQUNSUIHRMR-UHFFFAOYSA-M sodium;3-(1-phenylethyl)imidazole-4-carboxylate Chemical compound [Na+].C1=NC=C(C([O-])=O)N1C(C)C1=CC=CC=C1 GDSJQUNSUIHRMR-UHFFFAOYSA-M 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D233/90—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US55719475A | 1975-03-10 | 1975-03-10 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU677656A3 true SU677656A3 (ru) | 1979-07-30 |
Family
ID=24224401
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU762329945A SU677656A3 (ru) | 1975-03-10 | 1976-03-10 | Способ получени оптически активных низших алкил 1-(1-фенилэтил)-1н-имидазол-5-карбоксилатов |
Country Status (27)
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE871675A (fr) * | 1977-12-02 | 1979-04-30 | Smithkline Corp | Procede de preparation de derives de l'imidazole |
| JPS5671074A (en) | 1979-11-12 | 1981-06-13 | Takeda Chem Ind Ltd | 1,2-disubstituted-4-halogenoimidazole-5-acetic acid derivative |
| JPS5671073A (en) | 1979-11-12 | 1981-06-13 | Takeda Chem Ind Ltd | Imidazole derivative |
| JPS58157768A (ja) * | 1982-03-16 | 1983-09-19 | Takeda Chem Ind Ltd | ４−クロロ−２−フエニルイミダゾ−ル−５−酢酸誘導体 |
| PL149675B1 (pl) * | 1986-03-10 | 1990-03-31 | Sposób wytwarzania nowych pochodnych kwasu 1-metyl0-1h-imidaz0l0karb0ksyl0weg0-5 | |
| RU2144022C1 (ru) * | 1995-10-30 | 2000-01-10 | Такеда Кемикал Индастриз, Лтд. | Эфиры n-(бифенилметил)аминобензойной кислоты и способ их получения |
| WO2009146024A1 (en) | 2008-03-31 | 2009-12-03 | The General Hospital Corporation | Etomidate analogues with improved pharmacokinetic and pharmacodynamic properties |
| EA027976B1 (ru) | 2012-01-13 | 2017-09-29 | Дзе Дженерал Хоспитал Корпорейшн | Анестезирующие соединения и способы их применения |
-
1976
- 1976-02-13 CA CA245,697A patent/CA1066709A/en not_active Expired
- 1976-02-18 GB GB6339/76A patent/GB1535566A/en not_active Expired
- 1976-02-19 SE SE7601959A patent/SE7601959L/xx not_active Application Discontinuation
- 1976-02-23 ES ES445450A patent/ES445450A1/es not_active Expired
- 1976-03-01 FR FR7605762A patent/FR2318159A1/fr active Granted
- 1976-03-03 BE BE164793A patent/BE839120A/xx not_active IP Right Cessation
- 1976-03-05 CH CH280676A patent/CH629192A5/de not_active IP Right Cessation
- 1976-03-08 IT IT48460/76A patent/IT1057941B/it active
- 1976-03-08 JP JP51024280A patent/JPS51115473A/ja active Pending
- 1976-03-08 CS CS761495A patent/CS203116B2/cs unknown
- 1976-03-08 LU LU74503A patent/LU74503A1/xx unknown
- 1976-03-08 DE DE19762609573 patent/DE2609573A1/de not_active Withdrawn
- 1976-03-08 NO NO760790A patent/NO144884C/no unknown
- 1976-03-08 DK DK99376*#A patent/DK99376A/da not_active Application Discontinuation
- 1976-03-09 IE IE482/76A patent/IE42652B1/en unknown
- 1976-03-09 ZA ZA761427A patent/ZA761427B/xx unknown
- 1976-03-09 AT AT171776A patent/AT353262B/de not_active IP Right Cessation
- 1976-03-09 HU HU76JA00000750A patent/HU172026B/hu unknown
- 1976-03-09 AU AU11806/76A patent/AU503733B2/en not_active Expired
- 1976-03-09 NL NL7602444A patent/NL7602444A/xx not_active Application Discontinuation
- 1976-03-09 PT PT64879A patent/PT64879B/pt unknown
- 1976-03-09 FI FI760601A patent/FI62292C/fi not_active IP Right Cessation
- 1976-03-09 YU YU00608/76A patent/YU60876A/xx unknown
- 1976-03-10 IL IL49190A patent/IL49190A/xx unknown
- 1976-03-10 BG BG032575A patent/BG24806A3/xx unknown
- 1976-03-10 PL PL1976187827A patent/PL99926B1/pl unknown
- 1976-03-10 SU SU762329945A patent/SU677656A3/ru active
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