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

Temperature

80 °C

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).

1. extractionextracted with ether (3×25 mL)
2. washThe combined organic layer was washed with water (3×25 mL), brine (1×25 mL)
3. dry with materialdried (Na2SO4)
4. customThe solvent was evaporated under reduced pressure
5. customthe pale yellow syrupy residue thus obtained
6. customwas purified via Si-gel column chromatography (eluent: 10% ethyl acetate-hexane)

ORD record

ord-0876824632e94a67ad089896f660cffb

Source dataset

uspto-grants-2007_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07304164B1