Dimethyl Sulfate → 1-Methyl-2,4,5-trinitroimidazole

Participants

Reaction Conditions

Reaction Steps

A mixture of potassium salt of trinitroimidazole (100 mg, 0.41 mmol) and dimethylsulfate (1.0 g, excess) was heated in a preheated oil bath at 80° C. for about 2 h. The reaction mixture was diluted with water (50 mL) and extracted with ether (3×25 mL). The combined organic layer was washed with water (3×25 mL), brine (1×25 mL) and dried (Na2SO4). The solvent was evaporated under reduced pressure and the pale yellow syrupy residue thus obtained was purified via Si-gel column chromatography (eluent: 10% ethyl acetate-hexane). The pure product (64 mg, 71%) was obtained as a pale yellow solid. m.p: 84-85° C.; DSC: 84.81° C. (5° C./min); 1H NMR (Acetone-d6): 4.37 ppm; 13C NMR (Acetone-d6): 37.64, 133.46 (t), 136.05 (br) and 139.97 (t).

Provenance & Evidence