Diethyl Ether → Benzyl (1-methyl-1H-imidazol-2-yl)carbamate

HRID 741714Notes

Reaction equation

HRID 741714 reaction equation
Cl.[NH2:2][C:3]1[N:4]([CH3:8])[CH:5]=[CH:6][N:7]=1.[CH2:9]([O:16][C:17](Cl)=[O:18])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.CCOCC>[OH-].[Na+]>[CH2:9]([O:16][C:17]([NH:2][C:3]1[N:4]([CH3:8])[CH:5]=[CH:6][N:7]=1)=[O:18])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 10387Benzyl chloroformateHCID 101540761-Methyl-1H-imidazol-2-amine hydrochloride

Product 1

HCID 19426850Benzyl (1-methyl-1H-imidazol-2-yl)carbamate

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

2-Amino-1-methylimidazole hydrochloride (0.3 g) was dissolved in 1N sodium hydroxide solution (5 ml ). Benzyloxycarbonyl chloride (0.43 g) and ether (2 ml ) were added, and the mixture was stirred for 1 hour. The product was extracted with ethyl acetate, the extract was washed with water and aqueous saturated sodium chloride solution and dried over magnesium sulfate, and the solvent was evaporated under reduced pressure. Diethyl ether-hexane was added to the resulting residue for crystallization, and the crystals were separated by filtration. The crystals of 2-benzyloxycarbonylamino-1-methylimidazole thus obtained was dissolved in chloroform, and 4N hydrochloric acid-ethyl acetate (0.5 ml) was added to form its hydrochloric acid salt. The crude crystals thus obtained were washed with ether to give 2-benzyloxycarbonylamino-1-methylimidazole hydrochloride (0.2 g, Yield: 30% ) as white powder.

Workup

  1. extractionThe product was extracted with ethyl acetate
  2. washthe extract was washed with water and aqueous saturated sodium chloride solution
  3. dry with materialdried over magnesium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. additionDiethyl ether-hexane was added to the resulting residue for crystallization
  6. customthe crystals were separated by filtration

Sources & evidence

ORD record
ord-634ad6d74d3247fdba90e9c2cebf4ff9
Source dataset
uspto-grants-1996_09
Patent number
US05552427

Reaction notes

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