Hantzsch ester → 5-([4-[2-(4-Methylmercaptophenyl)ethoxy]phenyl]methyl)thiazolidine-2,4-dione
반응식
[CH3:1][S:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][O:11][C:12]2[CH:25]=[CH:24][C:15]([CH:16]=[C:17]3[S:21][C:20](=[O:22])[NH:19][C:18]3=[O:23])=[CH:14][CH:13]=2)=[CH:5][CH:4]=1.C(OC(C1CC(C(OCC)=O)=C(C)NC=1C)=O)C>>[CH3:1][S:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][O:11][C:12]2[CH:25]=[CH:24][C:15]([CH2:16][CH:17]3[S:21][C:20](=[O:22])[NH:19][C:18]3=[O:23])=[CH:14][CH:13]=2)=[CH:5][CH:4]=1참가 물질
반응 조건
- 온도
- 160 °C
실험 절차
1 g (2.7 mmole) 5-(4-[2-(4-methylmercaptophenyl)ethoxy]benzylidene)thiazolidine-2,4-dione and 1.36 g (5.4 mmole) diethyl-1,4-dihydro-2,6-dimethyl-3,5-pyridinedicarboxylate were mixed and heated to 160° C. under vacuum (when it melted), after 1 hour at this temperature the heat was removed. Toluene was added, crystals of the starting material was removed by filtration, the filtrate was evaporated and purified by chromatography on silica gel twice using first dichloromethane:methanol (98:2) and then diisopropyl ether as eluents. The reaction was restarted with unreacted material and 0.4 g diethyl-1,4-dihydro-2,6-dimethyl-3,5-pyridinedicarboxylate and kept at 160° C. for 2 hours. The product was boiled in diisopropyl ether, and purified by chromatography on silica gel using diisopropyl ether as eluent. The combined fractions gave 0.346 g (yield 36%) of the desired product.
후처리
- customwas removed
- additionToluene was added
- customcrystals of the starting material was removed by filtration
- customthe filtrate was evaporated
- custompurified by chromatography on silica gel
- custompurified by chromatography on silica gel
출처 및 근거
- ORD 기록
- ord-87987ba317964f018853e42c8d8d9569
- 출처 데이터셋
- uspto-grants-2001_09
- 특허 번호
- US06288096B1
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