Sodium Iodide → HCID 178483981, compound

Participants

Reaction Steps

A solution of 280 mg (0.5 mmol) of trans-4-Trifluoromethyl-benzenesulfonic acid 4-[methyl-(4-trifluoromethyl-benzenesulfonyl)-amino]-cyclohexylmethyl ester and 78 mg (0.55 mmol) of 2-dimethylaminoethanethiol hydrochloride in 4.5 ml DMF was treated at 0° C. with 48 mg (1.1 mmol) of 55% NaH, stirred for 20 h at RT. After cooling (0° C.) and treatment with a catalytic amount of NaI followed by 78 mg (0.55 mmol) of 2-dimethylaminoethanethiol hydrochloride and 48 mg (1.1 mmol) of 55% NaH the reaction mixture was stirred for 18 h at RT. The reaction was neutralized (aqueous 10% KHSO4, at 0° C.) and poured into aqueous sat. NaHCO3/Et2O (3×). The organic phases were washed with aqueous 10% NaCl solution, dried over Na2SO4 and evaporated. Purification by flash column chromatography on silica gel with CH2Cl2/MeOH (95:5) yielded 138 mg (63%) of trans-N-[4-(2-Dimethylamino-ethylsulfanylmethyl)-cyclohexyl]-N-methyl-4-trifluoromethyl-benzenesulfonamide, MS: 439 (MH+).

Provenance & Evidence