Water → 2-Chloro-N-(2,6-diisopropylphenyl)acetamide

Participants

Reaction Steps

Part A. A solution of 2,6-diisopropylaniline (10.0 mL, 53.0 mmol) and triethylamine (10.0 mL, 71.7 mmol) in tetrahydrofuran (100 mL) was cooled to 0° C., and treated dropwise with a solution of chloroacetyl chloride (5.00 mL, 62.8 mmol) in tetrahydrofuran (20 mL). After being stirred for 10 hours, the solution was poured into water (200 mL) and extracted with methylene chloride (2×200 mL). The extracts were combined, dried over anhydrous magnesium sulfate, filtered and evaporated to afford the product, N-(2,6-diisopropylphenyl)-2-chloroacetamide, as a solid. The solid was purified by trituration in boiling ether, filtration and drying; mp 157°-158° C. (10.7 g, 42.0 mmol, 79%). 1HNMR (CDCl3): δ 7.81 (1H, br s); 7.32 (1H, t, J=8.1 Hz); 7.19 (2H, d, J=8 Hz); 4.26 (2H, s); 3.02 (2H, heptet, J=6.6 Hz); 1.21 (12H, d, J=6.6 Hz). Mass spectrum (NH3 -CI/DDIP): m/z 271 (100%); 256 (11%); 255 (6%); 254 (30%); 219 (1%).

Provenance & Evidence