Chloroacetone → benzyl 2-amino-4-methyl-1H-imidazole-1-carboxylate

HRID 1160463Notes

Reaction equation

HRID 1160463 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C:12]([NH2:14])=[NH:13])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.Cl[CH2:23][C:24](=O)[CH3:25]>C(OCC)(=O)C>[NH2:13][C:12]1[N:11]([C:9]([O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[O:10])[CH:23]=[C:24]([CH3:25])[N:14]=1

Participants

5

Reactant 3

HCID 6571ChloroacetoneHCID 8471TriethylamineHCID 178513108HCID 178513108, compound

Product 1

HCID 57815123benzyl 2-amino-4-methyl-1H-imidazole-1-carboxylateYield 22%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of N-benzyloxycarbonylguanidine 1.93 g (10 mmol), triethylamine 1.39 ml (10 mmol), chloroacetone 2.40 ml (30 mmol) and ethyl acetate 40 ml was stirred at 50° C. for 10 hours. The reaction solution was washed with water and an aqueous sodium chloride solution and dried on magnesium sulfate. After evaporation of the solvent, the residue was purified by a column chromatography on silica gel and further recrystallized from n-hexane to give 500 mg of the title compound (yield: 22%).

Workup

  1. washThe reaction solution was washed with water
  2. dry with materialan aqueous sodium chloride solution and dried on magnesium sulfate
  3. customAfter evaporation of the solvent
  4. customthe residue was purified by a column chromatography on silica gel
  5. customfurther recrystallized from n-hexane

Sources & evidence

ORD record
ord-539e376ad4764f03a11c03978a6da236
Source dataset
uspto-grants-2010_10
Patent number
US07816387B2

Reaction notes

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