Acetazolamide synthesis

4synthesis methods

Product Name:Acetazolamide
CAS Number:59-66-5
Molecular formula:C4H6N4O3S2
Molecular Weight:222.25

Acetazolamide is 5-acetamido-1,3,4-thiadiazole-2-sulfonamide (9.7.5). The synthesis of acetazolamide is based on the production of 2-amino-5-mercapto-1,3, 4-thiadiazole (9.7.2), which is synthesized by the reaction of ammonium thiocyanate and hydrazine, forming hydrazino-N,N-bis-(thiourea) (9.7.1), which cycles into thiazole (9.7.2) upon reaction with phosgene. Acylation of (9.7.2) with acetic anhydride gives 2-acetylamino-5-mercapto-1,3,4-thiadiazol (9.7.3). The obtained product is chlorinated to give 2-acetylamino-5-mercapto-1,3,4-thiadiazol-5-sulfonylchloride (9.7.4), which is transformed into acetazolamide upon reaction with ammonia (9.7.5) [24,25].

2-(ACETAMIDO)-5-(CHLOROSULFONYL)-1,3,4-THIADIAZOLE

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Yield:59-66-5 74%

Reaction Conditions:

with 1,1,1-triphenylsilylamine in acetonitrile for 1 h;Reflux;Inert atmosphere;

Steps:

Preparation of sulfonamide products
General procedure: The sulfonyl chloride (1mmol) is dissolved in 15 ml acetonitrile and then silylamine (1 mmol) is addedslowly. The reaction mixture is refluxed for 1 hour and concentrated withrotary evaporator. If necessary, the product may be further purified by silicagel chromatography (hexane: ethyl acetate).

References:

Naredla, Rajasekhar Reddy;Klumpp, Douglas A. [Tetrahedron Letters,2013,vol. 54,# 45,p. 5945 - 5947] Location in patent:supporting information

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