Hydrochloric Acid → 3-Chloro-3-methyl-2-nitroso-1-(4-methyl-2-nitro-1H-imidazol-1-yl)butane

Participants

Reaction Conditions

Reaction Steps

Concentrated HCl (20 mL) was added from an addition flask to a mixture of 1-(4-methyl-2-nitro-1H-imidazol-1-yl)-3-methyl-2-butene (5.0 g, 25.64) and isoamyl nitrite (20 mL), keeping the temperature in the range of 0° C. to 5° C. After the addition the reaction mixture was stirred at ice-cold temperature for 30 minutes. The solid which formed was removed by filtration and washed with ice-cold ethanol. The solid was dispersed in acetonitrile, cooled to 0 ° C. and filtered to provide the title product as a light blue colored solid; yield: 4.97 g (62%); mp. 110°-1130 ° C. (decomp); 1H NMR (DMSO-d6) δ 1.81[s, 6H, C(CH3)2 ], 2.16(s, 3H, imi-CH3), 5.36(s, 2H, NCH2), 7.12(s, 1H, imi-CH) and 11.98(s, 1H, NOH). MS m/e 261 (M+H)+.

Provenance & Evidence