Sodium Thiosulfate → Benzenesulfonamide, N-[1-(3,5-dichlorobenzoyl)cyclohexyl]-4-methyl-

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Reaction Steps

To a stirred solution of N-{1-[(3,5-dichloro-phenyl)-hydroxy-methyl]-cyclohexyl}4-methyl-benzenesulfonamide in CH2Cl2 (4 mL) was added Dess-Martin reagent. The mixture was stirred for 6 hours and saturated aqueous NaHCO3 (5 mL) and solid Na2S2O3 (ca. 1 g) were added. After stirring for 30 min, the mixture was applied to a 10 mL Chem Elut cartridge and allowed to stand for 5 min. The cartridge was eluted with CH2Cl2 (25 mL) and the eluate was evaporated to leave the intended ketone (102 mg) as an oil. The crude product was dissolved in CH2Cl2 (4 mL) and stirred with PS-TsNHNH2 resin (100 mg, 0.28 mmol) for 3 hours. The mixture was filtered and washed with CH2Cl2 (5 mL), ether (5 mL), and CH2Cl2 (5 mL). The filtrate was evaporated to leave N-[1-(3,5-dichloro-benzoyl)-cyclohexyl]4-methyl-benzenesulfonamide (98 mg) as an oil. 1H NMR (500 MHz, CDCl3) δ(ppm): 7.8 (s, 2H), 7.6 (d, 2H), 7.4 (s, 1H), 7.2 (d, 2H), 5.75 (s, 1H), 2.35 (s, 3H), 1.9 (m, 2H), 1.8 (m, 2H), 1.4 (m, 3H), 1.3 (m, 2H), 1.2 (m, 1H).

Provenance & Evidence