Acetyl chloride → HCID 20290850, compound

Participants

Reaction Steps

To a solution of 4,5-bis(4-methoxyphenyl)-2-nitroimidazole (3.0 g, 9.22 mmole) and triethylamine (7 ml., 51 mmole) in 30 ml. THF at 0° C. under N2 was dropwise added a solution of acetyl chloride (1.3 ml., 18.4 mmole) in 5 ml. THF. After 2 hours at 0° C., the reaction mixture was diluted with ethyl acetate washed with 1 N HCl, saturated aqueous NaHCO3 and brine, dried and concentrated on a rotary evaporator. Crystallization from ether gave approximately 600 mg. of starting material. HPLC of the mother liquor and crystallization from ether gave 1-acetyl 4,5-bis(4-methoxyphenyl)-2-nitroimidazole, mp. 146°-151° C. H-NMR indicates purity >95%. H-NMR: 2.41δ(s, 3H), 3.8δ(s, 3H), 6.73-7.56 δ(2 AB quartets, J=9 Hz, 8H).

Provenance & Evidence