Formaldehyde → HCID 12011184, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 10 ml of glacial acetic acid and 10 ml of 37% formaldehyde is added 2.67 g (0.012 mol) of 1-(2′-chlorobenzyl)-4,5-dimethylimidazole. The mixture is stirred and heated in a sealed tube at 125-130° C. (oil bath temperature) overnight. After cooling, the solvent is evaporated in vacuo. The residue is subjected to chromatography on silica gel using dichloromethane-methanol (10:1) as eluent to give 2.39 g (79%) of 1-(2′-chlorobenzyl)-4,5-dimethyl-2-hydroxymethylimidazole as colorless powder. MS m/z (M++1) 251; 1H-NMR 400 MHz(δ, CDCl3): 1.94 (3H, s), 2.11 (3H, s), 4.53 (2H, s), 5.26 (2H, s), 6.42 (1H, dd, J=8, 1.2 Hz), 7.14(1H, td, J=8, 1.2Hz), 7.21 (1H, td, J=7.4, 1.6 Hz), 7.39 (1H, dd, J=8, 1.2 Hz) ppm.

Provenance & Evidence