Definition
ChEBI: 7-Sulfamoyl-1,2,4-benzothiadiazine 1,1-dioxide in which the hydrogen at position 6 is substituted by chlorine and that at position 3 is substituted by a benzylsulfanylmethyl group. A diuretic, it is used to treat hypertension and edema.
Manufacturing Process
The preparation of the dihydro analog is as follows:
(A) Preparation of 3-Chloromethyl-6-Chloro-7-Sulfamyl-3,4-DihydroBenzothiadizine-1,1-Dioxide - To 8 ml of 40-50% chloroacetaldehyde aqueous
solution and 7 ml of dimethylformamide are added 10 grams of 2,4-
disulfamyl-5-chloroaniline. The mixture is heated on a steam bath for 2 hours
after which it is concentrated at reduced pressure. The residue is triturated
with water. The solid material is recrystallized from methanol-ether after
treatment with activated carbon to give 7.2 grams of product, MP 229°-
230°C.
(B) Preparation of Benzylthiomethyl-6-Chloro-7-Sulfamyl-3,4-
Dihydrobenzothiadiazine-1,1-Dioxide - A mixture of 3-(chloromethyl)-6-chloro-
7-sulfamyl-3,4-dihydrobenzothiadiazine-1,1-dioxide (0.02 mol) and
benzylmercaptan (0.024 mol) in 20 ml of 10% sodium hydroxide and 20 ml of
dimethylformamide is stirred at room temperature for 6 hours. After heating
for 10 minutes on a steam bath, the mixture is cooled and acidified with 6 N
HCl. The product, after recrystallization from acetone, melts at 210°-211°C.
Safety Profile
Poison by intravenous route. Adiuretic and antihypertensive agent. When heated todecomposition it emits very toxic fumes of SOx, NOx, andCl
-.
