Triethylamine → [(2,4,6-Triisopropyl-phenyl)-acetyl]-sulfamic acid 4-cyano-2,6-diisopropyl-phenyl ester

Participants

Reaction Steps

Oxalyl chloride (0.48 mL, 5.5 mmol) was added dropwise to a solution of 2,4,6-triisopropylphenyl acetic acid (1.21 g, 4.6 mmol) in 100 mL toluene with 4 drops of N,N-dimethylformamide as a catalyst. The resulting solution was stirred overnight and then concentrated in vacuo. The residue was re-dissolved in 150 mL dichloromethane. 2,6-Bis(l-methylethyl)-4-cyanophenyl sulfamate (1.30 g, 4.6 mmol) and triethylamine (1.6 mL) were added, and the resulting mixture was stirred for 6 hours. Washed with 1 M HCl, dried the organic layer over magnesium sulfate, filtered, and concentrated to give an oily solid. Chromatography on silica gel (20% ethyl acetate/hexanes) gave 1.11 g of the title compound as a white solid; mp 79-84° C.

Provenance & Evidence