2-Nitroimidazole → (S)-(+)-alpha-(chloromethyl)-2-nitro-1H-imidazole-1-ethanol

Reaction equation

[N+:1]([C:4]1[NH:5][CH:6]=[CH:7][N:8]=1)([O-:3])=[O:2].C(=O)([O-])[O-].[K+].[K+].[CH2:15]([C@H:17]1[O:19][CH2:18]1)[Cl:16]>>[Cl:16][CH2:15][C@@H:17]([OH:19])[CH2:18][N:5]1[CH:6]=[CH:7][N:8]=[C:4]1[N+:1]([O-:3])=[O:2]

Participants

Reactant 3

HCID 107012-Nitroimidazole

HCID 11430Potassium Carbonate

HCID 149428(+)-Epichlorohydrin

Product 1

HCID 11052772(S)-(+)-alpha-(chloromethyl)-2-nitro-1H-imidazole-1-ethanol

Procedure

Alternatively, a mixture of 2-nitroimidazole, anhydrous potassium carbonate, and (S)-(+)-epichlorohydrin is refluxed for 10 minutes then filtered while hot. The filtrate is concentrated and cooled to give a solid. Crystallization from ethanol and further processing gives the product.