Thioacetamide → 5,6-Dihydro-2-methyl-6-(4-nitrobenzoyl)-4H-thiazolo[5,4-d] [1]benzazepine
Reaction equation
Br[CH:2]1[C:8](=O)[C:7]2[CH:10]=[CH:11][CH:12]=[CH:13][C:6]=2[N:5]([C:14](=[O:24])[C:15]2[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[CH:17][CH:16]=2)[CH2:4][CH2:3]1.[C:25]([NH2:28])(=[S:27])[CH3:26]>C(O)C>[CH3:26][C:25]1[S:27][C:2]2[CH2:3][CH2:4][N:5]([C:14](=[O:24])[C:15]3[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[CH:17][CH:16]=3)[C:6]3[CH:13]=[CH:12][CH:11]=[CH:10][C:7]=3[C:8]=2[N:28]=1Participants
4
Procedure
A mixture of 1.19 g of 4-bromo-1,2,3,4-tetrahydro-1(4-nitrobenzoyl)-5H-1benzazepin-5-one and 0.230 g of thioacetamide in 4 ml of ethyl alcohol is refluxed under argon for 18 hours. The volatiles are evaporated in vacuo to a residue which is partitioned between CHCl3 and 10% NaHCO3. The organic layer is separated and washed twice with water. The organic layer is separated, dried (MgSO4) and evaporated in vacuo to give 1.08 g of yellow foam which is purified by flash chromatography on silica by elution with 4% ethyl acetate in methylene chloride to give 560 mg of the desired product as pale yellow foam.