Reaction #75437

Reaction equation

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

1,3-diamino-2-methylpropane

→

title product

3-(3-Amino-2-methylpropylamino)-3-methyl-1-(2-nitroimidazolyl)-2-butanone Oxime

Solvents

acetonitrile

Conditions

Workup

1. 1
   workup.ADDITIONAfter the addition the reaction mixture
2. 2
   TemperatureThe reaction mixture was then cooled
3. 3
   Othersolvent was removed on a rotary evaporator to
4. 4
   Othera give a paste
5. 5
   OtherThis was crystallized from dichloromethane-ether

Procedure

3-Chloro-3-methyl-1-(2-nitroimidazolyl)-2-nitrosobutane (1.5 g, 6.09 mmol, Example 1) was added portionwise over a period of 30 minutes to a stirred solution of 1,3-diamino-2-methylpropane (3.0 g, 34.10 mmol) in dry acetonitrile (30 mL) at 50° C. After the addition the reaction mixture was allowed to remain at 50° C. for an additional 30 minutes. The reaction mixture was then cooled and solvent was removed on a rotary evaporator to a give a paste. This was crystallized from dichloromethane-ether to afford the title product as a light yellow solid; yield: 1.36 g (75%); mp. 102-104° C. (decomp); 1H NMR (CDCl3) δ0.89(d, 3H, CH3), 1.22[s, 6H, C(CH3)2], 1.51(m, 1H, CH3CH), 2.25(d, 2H, CH2NH2), 2.65(m, 2H, NHCH2), 5.31(s, 2H, imi-CH2), 7.03 & 7.21(2s, 2H, imi-H). MS m/e 299 (M+H)+.

Source