N-Formylmorpholine → N-(4-Morpholinylmethylene)-3-phenyl-1,2,4-thiadiazole-5-sulfonamide
Reaction equation
S(Cl)(Cl)=O.[C:5]1([C:11]2[N:15]=[C:14]([S:16]([NH2:19])(=[O:18])=[O:17])[S:13][N:12]=2)[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[CH:20]([N:22]1[CH2:27][CH2:26][O:25][CH2:24][CH2:23]1)=O>>[N:22]1([CH:20]=[N:19][S:16]([C:14]2[S:13][N:12]=[C:11]([C:5]3[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=3)[N:15]=2)(=[O:18])=[O:17])[CH2:27][CH2:26][O:25][CH2:24][CH2:23]1Participants
4
Procedure
Thionyl chloride (4.5 ml) was added dropwise to 3.0 g of 3-phenyl-1,2,4-thiadiazole-5-sulfonamide in 15 ml of dry N-formylmorpholine at -5°. The resulting mixture was stirred at room temperature for 3 hours, poured into ice water and stirred for 15 minutes. The solids were collected, washed with water, dried, triturated with ether, washed with hexane and dried (in vacuo, P2O5). Recrystallization from benzene/hexane gave 1.1 g of solid, m.p. 185°-187°.