|
| | BENZTHIAZIDE Basic information |
| Product Name: | BENZTHIAZIDE | | Synonyms: | 6-Chloro-3-[[(phenylMethyl)thio]Methyl]-2H-1,2,4-benzothiadiazine-7-sulfonaMide 1,1-Dioxide;((benzylthio)methyl)-3chloro-6dioxyde-1,1sulfonamide-7benzothiadiazine-1,2,;-1,-dioxide;2H-1,2,4-Benzothiadiazine-7-sulfonamide, 3-((benzylthio)methyl)-6-chloro-, 1,1-dioxide;2H-1,2,4-Benzothiadiazine-7-sulfonamide, 6-chloro-3-(((phenylmethyl)thio)methyl)-, dioxide;2H-1,2,4-Benzothiadiazine-7-sulfonamide, 6-chloro-3-[[(phenylmethyl)thio]methyl]-, 1,1-dioxide;2h-1,2,4-benzothiadiazine-7-sulfonamide,3-((benzylthio)menthyl)-6-chloro-,1,1;2h-1,2,4-benzothiadiazine-7-sulfonamide,6-chloro-3-(((phenylmethyl)thio)methyl | | CAS: | 91-33-8 | | MF: | C15H14ClN3O4S3 | | MW: | 431.94 | | EINECS: | 202-061-0 | | Product Categories: | Aromatics;Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals;Sulfur & Selenium Compounds;AQUATAG;Heterocyclic Compounds;Building Blocks;Chemical Synthesis;Heterocyclic Building Blocks;Others;S-Containing | | Mol File: | 91-33-8.mol |  |
| | BENZTHIAZIDE Chemical Properties |
| | BENZTHIAZIDE Usage And Synthesis |
| Originator | Exna,Robins,US,1960 | | Uses | Benzthiazide is a diuretic, antihypertensive agent. | | 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. | | Brand name | Aquatag
(Solvay Pharmaceuticals); Fovane (Pfizer). | | Therapeutic Function | Diuretic, Antihypertensive | | Safety Profile | Poison by intravenous route. Adiuretic and antihypertensive agent. When heated todecomposition it emits very toxic fumes of SOx, NOx, andCl-. |
| | BENZTHIAZIDE Preparation Products And Raw materials |
|
