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BENZTHIAZIDE

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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
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BENZTHIAZIDE Chemical Properties

Melting point:
231-232° (U.S. patent); mp 238-239° (P'an)
Boiling point:
680.6±65.0 °C(Predicted)
Density 
1.4176 (rough estimate)
refractive index 
1.6100 (estimate)
storage temp. 
Refrigerator
solubility 
DMSO (Slightly), Methanol (Slightly)
form 
Solid
pka
9.57±0.20(Predicted)
color 
White to Off-White
Water Solubility 
2.8mg/L(room temperature)
EPA Substance Registry System
2H-1,2,4-Benzothiadiazine-7-sulfonamide, 6-chloro-3-[[(phenylmethyl)thio]methyl]-, 1,1-dioxide (91-33-8)
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Safety Information

Hazard Codes 
Xn
Risk Statements 
42/43
Safety Statements 
26-36
WGK Germany 
2
RTECS 
DK8400000
Hazardous Substances Data
91-33-8(Hazardous Substances Data)
Toxicity
LD50 in mice, rats (mg/kg): >5000, >10000 orally; 410, 422 i.v. (P'an)

MSDS

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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-.

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