Reaction #75445

Reaction equation

1-(5-methyl-2-nitro-1H-imidazol-1-yl)-3-methyl-2-butene

isoamyl nitrite

HCl

→

3-Chloro-3-methyl-2-nitroso-1-(5-methyl-2-nitro-1H-imidazol-1-yl)butane

Yield 60.0%

Conditions

Workup

1. 1
   Otherdescribed for the preparation of its positional isomer (Example 27B) as a light blue solid

Procedure

3-Chloro-3-methyl-2-nitroso-1-(5-methyl-2-nitro-1H-imidazol-1-yl)butane was prepared in 60% yield from 1-(5-methyl-2-nitro-1H-imidazol-1-yl)-3-methyl-2-butene (1.0 g, 5.12 mmol, Example 27), isoamyl nitrite (5.0 mL) and concentrated HCl (5.0 mL) following the procedure described for the preparation of its positional isomer (Example 27B) as a light blue solid; mp. 102-105° C. (decomp); 1H NMR (DMSO-d6) δ1.73[s, 6H, C(CH3)2], 2.32(s, 3H, imi-CH3), 5.53(s, 2H, NCH2), 6.97(s, 1H, imi-CH) and 11.58(s, 1H, NOH). MS m/e 261 (M+H)+.

Source