91-33-8

Basic information

• Product Name: BENZTHIAZIDE
• Synonyms: ((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;3-((Benzylthio)methyl)-6-chloro-1,2,4-benzothiadiazine-7-sulfonamide 1,1-dioxide
• CAS NO: 91-33-8
• Molecular Formula: C₁₅H₁₄ClN₃O₄S₃
• Molecular Weight: 431.94
• EINECS: 202-061-0
• Product Categories: Heterocyclic Compounds;Building Blocks;Chemical Synthesis;Heterocyclic Building Blocks;Others;S-Containing;Aromatics;Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals;Sulfur & Selenium Compounds;AQUATAG
• Mol File: 91-33-8.mol
• Article Data: 0

Chemical Properties

• Melting Point: 231-232° (U.S. patent); mp 238-239° (P'an)
• Boiling Point: 680.6°C at 760 mmHg
• Flash Point: 365.4°C
• Appearance: /
• Density: 1.4176 (rough estimate)
• Vapor Pressure: 2.21E-18mmHg at 25°C
• Refractive Index: 1.6100 (estimate)
• Storage Temp.: Refrigerator
• Solubility: DMSO (Slightly), Methanol (Slightly)
• PKA: 9.57±0.20(Predicted)
• Water Solubility: 2.8mg/L(room temperature)
• CAS DataBase Reference: BENZTHIAZIDE(CAS DataBase Reference)
• NIST Chemistry Reference: BENZTHIAZIDE(91-33-8)
• EPA Substance Registry System: BENZTHIAZIDE(91-33-8)

Safety Data

• Hazard Codes: Xn
• Statements: 42/43
• Safety Statements: 26-36
• WGK Germany: 2
• RTECS: DK8400000
• Hazardous Substances Data: 91-33-8(Hazardous Substances Data)

Usage

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).

Safety Profile

Poison by intravenous route. Adiuretic and antihypertensive agent. When heated todecomposition it emits very toxic fumes of SOx, NOx, andCl-.

InChI:InChI=1/C15H14ClN3O4S3/c16-11-6-12-14(7-13(11)25(17,20)21)26(22,23)19-15(18-12)9-24-8-10-4-2-1-3-5-10/h1-7H,8-9H2,(H,18,19)(H2,17,20,21)