4-Toluenesulfonyl chloride → HCID 24966915, compound

Participants

Reaction Conditions

Reaction Steps

Following a procedure outlined in J. Org. Chem. 64, 1999, 2941-2943, sodium tert-butoxide (200 mg) and 1-cyclopropyl-1-(1-hydroxymethyl-2-methyl-propyl)-3-(2-trifluoromethyl-phenyl)-urea (245 mg) were added to THF (17 mL) and cooled to 0° C. To the mixture was added a solution of p-toluenesulfonyl chloride (170 mg) in THF (5 mL) slowly by syringe to give a suspension. The mixture was allowed to stir at RT for 12 hours and was then quenched by addition of ice cold water (15 mL). The mixture was extracted with ethyl acetate and the organic layer was separated, dried over Na2SO4 and evaporated. The crude material was purified by flash chromatography using ethyl acetate/heptane 1:1 as an eluent to give the desired material as yellow oil (170 mg). MS (ESI): 313.3 (MH+).

Provenance & Evidence