Sulfathiazole synthesis
- Product Name:Sulfathiazole
- CAS Number:72-14-0
- Molecular formula:C9H9N3O2S2
- Molecular Weight:255.32
Yield:-
Reaction Conditions:
Stage #1: 2-thiazolylamine;p-acetylaminobenzenesulfonyl chloridewith pyridine in tetrahydrofuran at 20; for 6 h;
Stage #2: with sodium hydroxide for 2 h;Reflux;
Steps:
2.3.2. General method for the preparation of 5f-5o
General procedure: 4-amino-N-(5-methylisoxazol-3-yl)benzenesulfonamide (5f).3-amino-5-methylisoxazole (1.18 g, 12 mmol) was added to thesolution of THF (20 mL) and pyridine (1 mL). The reaction mixturewas stirred at room temperature for 6 h after 4-acetamidobenzenesulfonyl chloride (2.34 g, 10 mmol) was added to the reaction solution. After the completion of the reactionmonitored by TLC, the solvent was remove. Then, 30 mL of 0.5 Mhydrochloric acid was added and a lot of precipitation wasprecipitated for filtration. The crude solid was washed with waterand directly used in the next step. All the intermediates were dissolvedin 20% NaOH solution and the reaction mixtures wereheated to reflux in an oil bath for 2 h. Then the reaction solutionwas quenched with 2 M hydrochloric acid to pH 7.4, resulting a lotof white solid. The crude product was obtained and washed with5*10 mL water, then dried overnight in a vacuum desiccator,yielding 5f as a white solid, yield 86%
References:
Wang, Lei;Li, Li;Zhou, Zi-Han;Jiang, Zheng-Yu;You, Qi-Dong;Xu, Xiao-Li [European Journal of Medicinal Chemistry,2017,vol. 136,p. 63 - 73]
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