Dichloromethane → HCID 20096923, compound

Participants

Reaction Conditions

Reaction Steps

A solution of bromoacetyl chloride (20.0 mL, 0.234 mol) in anhydrous dichloromethane (20 mL) was added dropwise to a cold (0° C.) mixture of 2,6-dimethylaniline (29.5 mL, 0.234 mol) and N-methylmorpholine (28.0 mL, 0.254 mol) in anhydrous dichloromethane (500 mL). The mixture was stirred at 0° C. for 1 h and at ambient temperature for 2 h before it was washed with 1N NaOH, 1N HCl and brine. Following drying and solvent evaporation, the residue was triturated with hot ether/ethyl acetate to yield after suction-filtration 46.75 g (83%) of the Formula V compound(s) as an off-white solid, m.p. 148°-149° C.; 1H NMR (300 MHz, CDCl3) δ 8.28 (br s, 1H), 7.08-6.97 (m, 3H), 4.14 (s, 0.5H), 3.93 (s, 1.5H), 2.16 and 2.15 (2s, 6H); 13C NMR (75 MHz, CDCl3) ppm 164.96, 135.63, 133.41, 128.44, 128.39, 127.78, 42.92, 29.04, 18.41; IR (KBr) 3440, 3212, 3042, 2974, 1644, 1534, 1476, 1308, 1218, 1120, 762 cm-1 ; MS (DCI) m/z 242.

Provenance & Evidence