Hantzsch ester → 5-([4-[2-(4-Methylmercaptophenyl)ethoxy]phenyl]methyl)thiazolidine-2,4-dione
反応式
[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]=1参加物
反応条件
- 温度
- 160 °C
実験手順
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.
後処理
- 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
出典と根拠
- ORDレコード
- ord-87987ba317964f018853e42c8d8d9569
- 出典データセット
- uspto-grants-2001_09
- 特許番号
- US06288096B1
反応ノート
読み込み中…