Reaction #75440

Reaction equation

3-Chloro-3-methyl-1-(2-nitroimidazolyl)-2-nitrosobutane

1,3-diaminopropane

acetonitrile

→

title compound

3-(Aminopropyl)-3-methyl-1-(2-nitroimidazolyl)-2-butanone Oxime

Conditions

Workup

1. 1
   workup.ADDITIONAfter the addition
2. 2
   TemperatureThe reaction mixture was then cooled
3. 3
   Filtrationfiltered

Procedure

3-Chloro-3-methyl-1-(2-nitroimidazolyl)-2-nitrosobutane (1.00 g, 4.06 mmol,Example 1) was added in portions over a period of 20 minutes to a stirred solution of 1,3-diaminopropane (1.0 g, 13.50 mmol) in dry acetonitrile at 50° C. After the addition, the reaction mixture was maintained at 50° C. for an additional 30 minutes. The reaction mixture was then cooled and filtered to provide the title compound as a yellow colored solid. For further purification, the solid was suspended in a small amount of water, stirred and filtered to afford the title product in >97% purity; yield: 0.78 g, (68%); mp. 136-137° C. 1H NMR (DMSO-d6) δ1.19[s, 6H, C(CH3)3], 1.37(m, CH2CH2CH2), 1.52(bs, 1N, NH), 2.21 & 1.54(2t, 4H, NHCH2), 5.22(s, 2H, imida-CH2), 7.05 & 7.27(2s, 2H, imida-ring H) and 11.42(bs, 1H, NOH). MS m/e 285 (M+H)+.

Source