Ammonia → (2-Ethyl-1H-imidazol-5-yl)methanol

Reaction equation

[OH:1][CH:2](O)[C:3](=O)[CH3:4].[NH3:7].Cl.[C:9](=[NH:15])(OCC)[CH2:10][CH3:11]>>[CH2:10]([C:9]1[NH:15][C:3]([CH2:2][OH:1])=[CH:4][N:7]=1)[CH3:11]

Participants

Reactant 3

HCID 222Ammonia2×

HCID 13000588Ethyl propanecarboximidate hydrochloride

HCID 131809821,1-Dihydroxypropan-2-one

Product 1

HCID 12528982(2-Ethyl-1H-imidazol-5-yl)methanol

Conditions

Temperature: 90 °C

Procedure

Dihydroxyacetone (65 g) was added slowly to liquid ammonia (250-300 ml), followed by ethyl propanimidate hydrochloride (65 g). The suspension was transferred to an autoclave and heated at 90° C. for 16 h. The ammonia was allowed to evaporate and then the reaction mixture concentrated in vacuo. The residue was dissolved in methanol, washed with charcoal, and then purified by chromatography, eluting with a gradient of System C (300:8:1 to 50:8:1). Trituration with acetone gave the title compound (29.83 g) as a white solid.