Acetic acid, 2,2-dimethoxy-, methyl ester → N-(5-chloro-2-fluorobenzyl)-2,2-dimethoxyacetamide

Participants

Reaction Steps

Equimolar amounts of 2-fluoro-5-chlorobenzylamine (10.0 g, 62.5 mmol) and methyl dimethoxyacetate (8.38 g, 62.5 mmol) were heated in a sealed tube at 100° C. for 16 h. After cooling to RT, to the reaction mixture was added n-heptane (40 mL) and cooled at 4° C. overnight. The solid formed was filtered off and dried in vacuo to give the title compound as off-white solid. 1H NMR (CDCl3, 300 MHz): δ=3.40 (s, 6H), 4.52 (d, J=5.8 Hz, 2H), 4.74 (s, 1H), 6.89 (bs, 1H), 7.01 (t, J=8.4 Hz, 1H), 7.20-7.25 (m, 1H), 7.31-7.36 (m, 1H). MS (ES+): m/z 261.90/263.78 [MH+]. HPLC: tR=2.85 min (ZQ2, polar—5 min).

Provenance & Evidence