Chloroacetyl chloride → 4-chloroacetyl-9,10-dihydro-3-methyl-4H-thieno[3,4-b][1,5]benzodiazepin-10-one
Reaction equation
[CH3:1][C:2]1[S:3][CH:4]=[C:5]2[C:11](=[O:12])[NH:10][C:9]3[CH:13]=[CH:14][CH:15]=[CH:16][C:8]=3[NH:7][C:6]=12.[Cl:17][CH2:18][C:19](Cl)=[O:20]>O1CCOCC1>[Cl:17][CH2:18][C:19]([N:7]1[C:8]2[CH:16]=[CH:15][CH:14]=[CH:13][C:9]=2[NH:10][C:11](=[O:12])[C:5]2=[CH:4][S:3][C:2]([CH3:1])=[C:6]12)=[O:20]Participants
4
Procedure
8 g of 9,10-dihydro-3-methyl-4H-thieno[3,4-b][1,5]benzodiazepin-10-one and 5.6 ml of chloroacetyl chloride are boiled in 160 ml of dioxane (containing 8 g of ground potassium carbonate) under reflux for 8 hours. The thus-obtained suspension is concentrated to dryness; the resulting residue is taken up in toluene; the toluene mixture is washed with sodium bicarbonate solution and then with water, and the toluene solution is dried over sodium sulfate. Concentration of the dried toluene solution yields 4-chloroacetyl-9,10-dihydro-3-methyl-4H-thieno[3,4-b][1,5]benzodiazepin-10-one (m. 156° to 158° C.).