Methanesulfonyl chloride → HCID 11576899, compound

Participants

Reaction Steps

A solution of 4-[{2-[(4-aminophenyl)thio]ethyl}(2,2,2-trifluoroethyl)amino]-2-(trifluoromethyl)benzonitrile (0.038 g, 0.091 mmol; see Example 74A) in CH2Cl2 (4 mL) was treated under N2 with TEA (0.010 g, 0.099 mmol) and MsCl (0.011 g, 0.099 mmol) and stirred at rt. After 4 h, additional TEA (0.0046 g, 0.046 mmol) and MsCl (0.0052 g, 0.046 mmol) were added and stirred at rt. After 1 h, the mixture was concentrated in vacuo and the residue taken up in CHCl3 (4 mL) and heated at 70° C. for 2 h. Upon cooling, additional TEA (0.0046 g, 0.046 mmol) and MsCl (0.0052 g, 0.046 mmol) were added and heated at 70° C. for 12 h. Upon cooling, additional TEA (0.0092 g, 0.091 mmol) and MsCl (0.0104 g, 0.091 mmol) were added and heated at 70° C. for 4 h. The mixture was partitioned between EtOAc and 0.1N HCl. The organic phase was washed with 0.1N HCl and brine, dried (Na2SO4) and concentrated in vacuo. The residue was purified by silica gel chromatography (5-80% EtOAc/hexanes gradient) to give the title compound (0.025 g, 55% yield): MS (ES) m/z 496 (M−1).

Provenance & Evidence