BENZTHIAZIDE Property

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)

Safety

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)

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Danger

Hazard statements

H317May cause an allergic skin reaction

H334May cause allergy or asthma symptoms or breathing difficulties if inhaled

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P342+P311IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.

BENZTHIAZIDE Chemical Properties,Usage,Production

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^-.