carbutamide Chemical Properties

Melting point:

144-145°

Density 

1.2840 (rough estimate)

refractive index 

1.6630 (estimate)

storage temp. 

Refrigerator

solubility 

DMSO (Slightly), Methanol (Slightly)

form 

Solid

pka

pKa 5.75(H2O t=25±0.02 I=0.2) (Uncertain)

color 

Off-White to Pale Beige

Water Solubility 

535.2mg/L(37 ºC)

EPA Substance Registry System

Benzenesulfonamide, 4-amino-N-[(butylamino)carbonyl]- (339-43-5)

Safety Information

Hazardous Substances Data

339-43-5(Hazardous Substances Data)

Toxicity

LD50 s.c. in mice: 3 g/kg (Haack, Hagedorn)

carbutamide Usage And Synthesis

Chemical Properties

Off-White to Pale Peach Solid

Originator

Carbutamide,Servier

Uses

Antidiabetic.

Definition

ChEBI: Carbutamide is a sulfonamide and a member of benzenes.

Manufacturing Process

223 g of the sodium salt of acetylsulfaniamide are stirred with 223 ml of triethylene glycol. 118 g of n-butyl isothiocyanate are added to the resulting homogeneous mixture. The resulting syrup is heated to 85°C for 4 hours. The mixture is then stirred with 1000 ml of chloroform and 1000 ml of water. The chloroform layer is twice shaken with water, each time with 250 ml. The aqueous extracts are combined and rendered weakly alkaline to phenolphthalein by addition of hydrochloric acid. Unreacted acetyl sulfanilamide precipitates and filtered off. The filtrate is acidified to a pH of 6.5 by the addition of HCl. An oily precipitate settles from the reaction solution and is separated therefrom. N-Butyl acetyl sulfanilylthiourea is precipitated from mother liquors obtained thereby by addition of HCl until Congo paper changes its color to blue. 210 g N-butyl acetyl sulfanilylthiourea are dissolved in 1400 ml of acetone while heating. The solution is mixed with 500 ml of water. A solution of 63 g of sodium nitrite in 120 ml of water is added thereto within about 45 minutes while stirring and cooling to 15°-20°C.
A suspension of crystals is obtained. 240 ml of 25% glacial acid are added thereto within 30 minutes. Stirring of the mixture is continued for 6 hours. N-Butyl acetyl sulfanilylurea mixed with sulfur is precipitated and filtered off. The crude reaction product is suspended in 1000 ml of water and is rendered weakly alkaline to phenolphthalein. Undissolved sulfur is filtered off. The filtrate is acidified by the addition of HCl. 250 g of N-butyl acetyl sulfanilylthiourea having a melting point of 186°-189°C are obtained. It is heated with 500 ml of 5 N potassium hydroxide solution to a temperature of 92°C for 2 hours while stirring. The solid reaction product is dissolved by heating with 750 ml of water and is purified by means of activated charcoal. The resulting solution is heated to 60°C and acidified by addition of HCl. 187 g of N-butyl acetyl sulfanilylthiourea melting at 139°-141°C obtained thereby.

Therapeutic Function

Oral hypoglycemic

Safety Profile

A poison by intraperitoneal route. Moderately toxic by ingestion and subcutaneous routes. An experimental teratogen. Other experimental reproductive effects. When heated to decomposition it emits very toxic fumes of NO, and SOx.

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