Acetic acid, 2,2-dimethoxy-, methyl ester → N-[(2-Chlorophenyl)methyl]-2,2-dimethoxyacetamide

Participants

Reaction Conditions

Reaction Steps

A mixture of methyl dimethoxyacetate (1.41 g, 10.4 mmol) and 2-chlorobenzylamine (1.45 g, 9.73 mmol) in a microwave vial was sealed and heated in the microwave reactor to 130° C. for 30 min and then to 140° C. for 40 min. The reaction solution was dissolved in EtOAc (≈60 mL) and washed with dil. HCl, water, sat. Na2CO3 solution, and brine, and dried over MgSO4. The EtOAc extract was filtered, concentrated, and dried in vacuo overnight, giving the title compound as pale yellow oil. 1H NMR (400 MHz, CDCl3): δ=7.41-7.35 & 7.27-7.22 (AA′BB′, 4H), 6.98 (brs, 1H), 4.74 (s, 1H), 4.58 (d, J=6.0 Hz, 2H), 3.40 (s, 6H). MS(ES+): m/z=266.05/268.01 (41/13) [MNa′], 244.07/246.02 (86/58) [MH+], 212.03/214.02 (56/21) [MH+-MeOH], 180.07/182.05 (63/26) [MH+-2 MeOH]. HPLC: tR=2.87 min (polar—5 min, ZQ3).

Provenance & Evidence