4-AMINO-N-(5-ETHYL-[1,3,4]THIADIAZOL-2-YL)-BENZENESULFONAMIDE

Originator

Sul-Spansion,SKF,US,1956

Definition

ChEBI: 4-amino-N-(5-ethyl-1,3,4-thiadiazol-2-yl)benzenesulfonamide is a member of benzenes and a sulfonamide.

Manufacturing Process

0.163 mol of 2-amino-5-ethyl-1,3,4-thiadiazole was covered with 43 parts of anhydrous pyridine. To the mixture was added 50 parts (0.214 mol) of pacetylaminobenzenesulfonyl chloride with vigorous shaking at 50°C to 60°C. The reaction mixture was then heated to 125°C. When the mixture had cooled somewhat it was placed in a Claisen flask and 27.6 parts (0.69 mol) of sodium hydroxide dissolved in 110 parts of water was added through a dropping funnel while distilling off a mixture of pyridine and water. The distillation was stopped when the temperature reached 100°C and the residual liquor in the flask heated at 95°C for 30 minutes.The reaction mixture was then poured into 1,650 parts of hot water, the pH adjusted to 8 to 9, decolorizing charcoal was added and the whole was heated on the steam for 15 minutes. The charcoal was filtered off and the hot filtrate neutralized and cooled. The 2-(sulfanilamido)-5-ethyl-1,3,4-thiadiazole was purified by repeated crystallization from boiling water.

Therapeutic Function

Antibacterial