Reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]2[S:12][CH:13]=[C:14]([C:16]3[CH:17]=[C:18]4[C:23](=[CH:24][CH:25]=3)[NH:22][C:21](=[O:26])[CH2:20][CH2:19]4)[N:15]=2)[CH:6]=[CH:7][C:8]=1[S:9][CH3:10].C(=O)([O-])[O-:28].[Na+].[Na+]>C(Cl)(Cl)Cl.C(O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]2[S:12][CH:13]=[C:14]([C:16]3[CH:17]=[C:18]4[C:23](=[CH:24][CH:25]=3)[NH:22][C:21](=[O:26])[CH2:20][CH2:19]4)[N:15]=2)[CH:6]=[CH:7][C:8]=1[S:9]([CH3:10])=[O:28]Participants
Procedure
In 150 ml of chloroform-ethanol was suspended 3.40 g of 2-(3-methoxy-4-methylthiophenyl)-4-(3,4-dihydrocarbostyril-6-yl)thiazole. Thereto was added, in small portions, 1.97 g of methachloroperbenzoic acid (80%) under ice-cooling. The mixture was stirred for 1 hour. Then, the mixture was returned to room temperature and stirred overnight. Thereto was added an aqueous sodium carbonate solution. The mixture was extracted with chloroform three times. The combined extract was washed with a saturated aqueous sodium chloride solution and dried over magnesium sulfate. The solvent was distilled off and the resulting crystals were recrystallized from dimethylformamide to obtain 0.50 g of 2-(3-methoxy-4-methylsulfinylphenyl)-4-(3,4-dihydrocarbostyril-6-yl)thiazole as light yellow acicular crystals.
Workup
- temperaturecooling
- customwas returned to room temperature
- stirringstirred overnight
- extractionThe mixture was extracted with chloroform three times
- extractionThe combined extract
- washwas washed with a saturated aqueous sodium chloride solution
- dry with materialdried over magnesium sulfate
- distillationThe solvent was distilled off
- customthe resulting crystals were recrystallized from dimethylformamide
Sources & evidence
- ORD record
- ord-8cf10254c8e84bf4b95a9cf2c8a1c892
- Source dataset
- uspto-grants-2000_06
- Patent number
- US06080764
Linked notes
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