2043-38-1

Off-White Solid

Saltucin,Boehringer Mannheim,W. Germany,1961

Diuretic and antihypertensive.

ChEBI: Butizide is a benzothiadiazine.

Chlorsulfonic acid and 3-chloroaniline react to give an intermediate which when treated with ammonia yields 5-chloro-2,4-disulfamylaniline.
20 g of 5-chloro-2,4-disulfamylaniline in 15 cc of diethyleneglycol-dimethyl ether with 0.9 g of isovaleraldehyde are reacted in the presence of 0.5 cc of a saturated solution of hydrochloric acid in ethyl acetate at 80°-90°C. The reaction mixture is concentrated under reduced pressure, an oily product precipitates on the addition of water, the latter is decanted and ethanol added to the remaining oil. 3-Isobutyl-6-chloro-7-sulfamyl-3,4-dihydro-1,2,4- benzothiadiazine-1,1-dioxide crystallizes and, after recrystallization from dimethylformamide and water, melts at 241°-245°C.

Diuretic, Antihypertensive