Synthesis Of 4-Methylbenzenesulfonamide Synthesis Lab Report

Synthesis of (S)-N-(1-(1H-benzo[d][1,2,3]triazol-1-yl)-3-(1H-indol-3-yl)-1-oxopropan-2-yl)-4-methylbenzenesulfonamide (3).
A mixture of p-toluenesulfonyl chloride(0.95 g, 5 mmol) and DMAP (0.08 g, 0.65 mmol) was stirred in methylene chloride (5 mL) for 10 min, compound 2 ( 1.8 g., 5 mmol) was dissolved in methylene chloride (5 mL) containing TEA (0.21 mL, 1.5mmol) and the resulting solution was added to the reaction mixture. After 20 min, benzotriazole (0.72 g, 6 mmol) was added and the reaction was allowed to stir for additional 1.5 hrs at 25 oC. Upon completion of the reaction (monitored by TLC) CH2Cl2 (50 mL) was added and the organic layer was washed with saturated Na2CO3 (10 mL, 3x), water (10 mL, 2x) andbrine
(10 mL, 1x). The organic layer was dried over anhydrous sodium sulfate and hexane (20mL) was added. The solid separated was filtered and dried under vacuum to give the target N-acylbenzotriazoles (2.1 g, 92%).
Synthesis of (S)-N-hydroxy-3-(1H-indol-3-yl)-2-(4-methylphenyl-sulfonamido) propanamide (II).
To a solution of 3 (1.37.g, 3 mmol) in methylene chloride (20 mL), hydroxylamine HCl (0.42 g, 6mmol) and TEA (0.84 mL, 6mmol) were added. The mixture was stirred at 25 oC for 1 hr. The reaction was diluted with methylene chloride (40 mL) then, washed with 6NHCl (3 × 10 mL), water (2 × 10 mL) and brine (1 × 10 mL). The organic layer was dried over anhydrous sodium sulfate and filtered. The filtrate was evaporated under vacuum to afford compound II (yield 1.00 g,
90%).