N,O-Dimethylhydroxylamine → HCID 86607369, compound

Participants

Reaction Steps

Part B: To a magnetically stirred solution of N-benzyl-5-methyl-1H-imidazole-4-carboxylic acid (6.77 gram, 0.031 mol) in anhydrous acetonitrile (35 ml) was successively added diisopropylethylamine (DIPEA) (17.2 ml, 0.0992 mol), HBTU (14.098 gram, 0.0372 mol) and methoxy-methylamine (3.63 gram, 0.0372 mol). The resulting mixture was reacted at 20° C. for 16 hours and subsequently concentrated in vacuo. The resulting residue was taken up in ethylacetate and successively washed with 5% aqueous NaHCO3 solution and water. The organic layer was dried over MgSO4, filtered and concentrated in vacuo. The resulting oily residue (18.45 gram) was purified by flash chromatography (ethyl acetate/acetone=7/3 (v/v)) to give N-methoxy-N-methyl-5-methyl-1-benzyl-1H-imidazole-4-carboxamide (10.77 gram, 82% yield). MH+=260. 1H-NMR (400 MHz, CDCl3): 2.34 (s, 3H), 3.47 (s, 3H), 3.77 (s, 3H), (s, 2H), 7.05-7.10 (m, 2H), 7.18-7.28 (m, 3H), 7.48 (s, 1H).

Provenance & Evidence