ChemicalBook CAS DataBase List 2-Thiazolesulfonyl chloride

2-Thiazolesulfonyl chloride synthesis

4synthesis methods

Product Name:2-Thiazolesulfonyl chloride
CAS Number:100481-09-2
Molecular formula:C3H2ClNO2S2
Molecular Weight:183.64

288-47-1 Synthesis

288-47-1
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$6.00/1g

100481-09-2
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$195.00/50mg

Yield: 54%

Reaction Conditions:

with N-chloro-succinimide;n-butyllithium;sulfur dioxide in tetrahydrofuran;hexane

Steps:

140.A A.
A. Thiazole-2-sulfonyl chloride Thiazole (0.51 g, 6 mmol) was dissolved in THF (5 ml) and cooled to -78° C. under argon atmosphere. n-Butyllithium (2.5M solution in hexane, 2.4 ml, 6 mmol) was added dropwise under constant stirring. The resultant reaction mixture was stirred at -78° C. for 40 min. Sulfur dioxide was bubbled through the reaction mixture for 15 min at -78° C. The reaction mixture was allowed to attain ambient temperature slowly and stirred for 30 min. NCS was added and stirring was continued for 30 min. The reaction mixture was diluted with water (50 ml), extracted with ethyl acetate (2*50 ml) and the combined organic layer was dried over anhydrous MgSO₄. Removal of the solvent under reduced pressure gave crude product which was purified by column chromatography, using hexane as eluent, to give thiazole-2-sulfonyl chloride as a liquid(0.6 g, 54% yield).

References:

Texas Biotechnology Corporation US5571821, 1996, A