Reaction #1055342

Reaction equation

HCl

1-(4-methyl-2-nitro-1H-imidazol-1-yl)-3-methyl-2-butene

isoamyl nitrite

→

title product

3-chloro-3-methyl-2-nitroso-1-(4-methyl-2-nitro-1H-imidazol-1-yl)butane

Conditions

Workup

1. 1
   Otherin the range of 0° C. to 5° C
2. 2
   workup.ADDITIONAfter the addition the reaction mixture
3. 3
   OtherThe solid which formed
4. 4
   Otherwas removed by filtration
5. 5
   Washwashed with ice-cold ethanol
6. 6
   workup.ADDITIONThe solid was dispersed in acetonitrile
7. 7
   Filtrationfiltered

Procedure

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. 110-113° 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)+.

Source