Cyclobutylamine → 1-cyclobutyl-4-nitro-1H-imidazole

HRID 1793182Notes

Reaction equation

HRID 1793182 reaction equation
[N+]([N:4]1[CH:8]=[C:7]([N+:9]([O-:11])=[O:10])[N:6]=[CH:5]1)([O-])=O.[CH:12]1(N)[CH2:15][CH2:14][CH2:13]1>CO>[CH:12]1([N:4]2[CH:8]=[C:7]([N+:9]([O-:11])=[O:10])[N:6]=[CH:5]2)[CH2:15][CH2:14][CH2:13]1

Participants

4

Reactant 2

HCID 75645CyclobutylamineHCID 51694961,4-Dinitro-1H-imidazole

Product 1

HCID 113896111-cyclobutyl-4-nitro-1H-imidazoleYield 92%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1,4-Dinitroimidazole (237 mg, 1.5 mmol, J. Phys. Chem. 1995, 99, 5009–5015) was added to a solution of cyclobutylamine (107 mg, 1.5 mmol) in methanol (10 mL) at 23° C. The reaction mixture was stirred for 16 h, then the solvent was removed in vacuo and the resulting residue was purified by silica gel chromatography (1:1 hexanes-ethyl acetate) to afford 230 mg (92% yield) of 1-cyclobutyl-4-nitro-1H-imidazole; 1H NMR (400 MHz, CDCl3) δ 7.81 (s, 1H), 7.45 (s, 1H), 4.64 (m, 1H), 2.6 (m, 2H), 2.4 (m, 2H), 2.0 (m, 2H); MS (AP/CI): 168.2 (M+H)+. Note: 1,4-Dinitroimidazole is a highly energetic, semi-stable substance and should be stored in a freezer at all times it is not in use. Thermodynamic measurements have shown that it can potentially generate enough energy at 35° C. under adiabatic conditions to violently explode. Extreme caution should be exercised at all times using this material.

Workup

  1. customthe solvent was removed in vacuo
  2. customthe resulting residue was purified by silica gel chromatography (1:1 hexanes-ethyl acetate)

Sources & evidence

ORD record
ord-d519d927b6524e8eba036b10bc73760b
Source dataset
uspto-grants-2006_07
Patent number
US07078529B2

Reaction notes

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