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

HRID 353911Notes

Reaction equation

HRID 353911 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) δ7.81 (s, 1H), 7.45 (s, 1H), 4.64 (m, 1H), 2.6 (m, 2H), 2.4 (m, 2H), 2.0 (m, 2H); MS (AP/Cl): 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-81f9327cd9f541ff8c15345c89075ca0
Source dataset
uspto-grants-2004_06
Patent number
US06756385B2

Reaction notes

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