N-Chloro-N-cyclohexylbenzenesulfonamide

Abstract

[15963-66-3] C12H16ClNO2S (MW 273.78) InChI = 1S/C12H16ClNO2S/c13-14(11-7-3-1-4-8-11)17(15,16)12-9-5-2-6-10-12/h2,5-6,9-11H,1,3-4,7-8H2 InChIKey = RWVOAAWFMJRINI-UHFFFAOYSA-N (used for radical chlorination at allylic1, 4 or benzylic carbon1) Physical Data: mp 42 °C. Solubility: sol benzene, CCl4, CHCl3, CH2Cl2; insol H2O, petroleum ether. Analysis of Reagent Purity: mp, NMR, combustion analysis. Preparative Methods: N-cyclohexylbenzenesulfonamide can be prepared by addition of benzenesulfonyl chloride to a solution of cyclohexylamine in pyridine and purified by recrystallization from ethanol. N-Chlorination is accomplished by treating a solution of N-cyclohexylbenzenesulfonamide in dichloromethane with NaOCl solution at 0 °C followed by dropwise addition of glacial acetic acid.1 Alternatively, a suspension of N-cyclohexylbenzenesulfonamide in acetic acid can be treated with NaOCl solution or powdered N-cyclohexylbenzenesulfonamide can be added to a solution containing NaHCO3 and NaOCl.2 Purification: precipitation from CHCl3 solution by addition of petroleum ether or trituration with petroleum ether. Handling, Storage, and Precautions: to avoid decomposition, this reagent should be protected from prolonged exposure to light and moisture. Store under nitrogen in the dark. This toxic reagent should be handled in a fume hood.