Potassium Carbonate → n-(5-Oxo-5,6,7,8-tetrahydro-naphthalene-2-carbonyl)-methanesulfonamide

Participants

Reaction Conditions

Reaction Steps

A sample of 5-Oxo-5,6,7,8-tetrahydro-naphthalene-2-carboxylic acid amide (Example 81, Step 1) (29.4 mg, 0.16 mmol) in tetrahydrofuran (71 μL) is treated with K2CO3 (36.5 mg, 0.26 mmol), powdered KOH (32.9 mg, 0.82 mmol) and tetrabutylammonium hydrogen sulfate (2.6 mg, 0.008 mmol) in that order. The reaction is warmed to 55° C. and vigorously stirred for 20 minutes. Then a solution of methanesulfonyl chloride (23.2 mg, 0.20 mmol) in tetrahydrofuran (140 μL) is added over 20 minutes and the reaction was stirred at 55° C. overnight. The reaction is then cooled to room temperature, diluted with ethyl acetate and extracted with water twice. The organic phase is then dried over MgSO4, filtered and the solvent is removed. The crude sulfonamide (35.5 mg 86% yield) is taken on without purification; LC/MS calculated for [M+H]+ C12H13NO4S: 268.1, found: 268.1.

Provenance & Evidence