N-Formylmorpholine → N-(4-Morpholinylmethylene)-3-(2-methylphenyl)-1,2,4-thiadiazole-5-sulfonamide

Reaktionsgleichung

[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[N:12]=[C:11]([S:13]([NH2:16])(=[O:15])=[O:14])[S:10][N:9]=1.S(Cl)(Cl)=O.[CH:21]([N:23]1[CH2:28][CH2:27][O:26][CH2:25][CH2:24]1)=O>>[N:23]1([CH:21]=[N:16][S:13]([C:11]2[S:10][N:9]=[C:8]([C:3]3[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=3[CH3:1])[N:12]=2)(=[O:15])=[O:14])[CH2:28][CH2:27][O:26][CH2:25][CH2:24]1

Komponenten

Edukt 3

HCID 20417N-Formylmorpholine

HCID 24386Thionyl Chloride

HCID 141831333-(2-Methylphenyl)-1,2,4-thiadiazole-5-sulfonamide

Produkt 1

HCID 54556514N-(4-Morpholinylmethylene)-3-(2-methylphenyl)-1,2,4-thiadiazole-5-sulfonamide

Versuchsvorschrift

To a solution of 3.5 g of 3-(2-methylphenyl)-1,2,4-thiadiazole-5-sulfonamide in 18 ml of N-formylmorpholine at -5° C. was added 5 ml of thionyl chloride. The resulting mixture was stirred for 3 hours at room temperature, then poured into ice water and stirred for 30 minutes. The solid was collected, washed with water and sucked dry. The solid was then triturated with ether, ether/hexane (1:1) and hexane successively. The product was dried (P2O5) to give 4.52 g of solid, m.p. 151°-153° C.