Ammonia → (2-Ethyl-1H-imidazol-5-yl)methanol

HRID 1492758Notes

Reaction equation

HRID 1492758 reaction equation
[OH:1][CH:2](O)[C:3](=O)[CH3:4].[NH3:7].Cl.[C:9](=[NH:15])(OCC)[CH2:10][CH3:11]>>[CH2:10]([C:9]1[NH:15][C:3]([CH2:2][OH:1])=[CH:4][N:7]=1)[CH3:11]

Participants

4

Reactant 3

HCID 222Ammonia2×HCID 13000588Ethyl propanecarboximidate hydrochlorideHCID 131809821,1-Dihydroxypropan-2-one

Product 1

HCID 12528982(2-Ethyl-1H-imidazol-5-yl)methanol

Conditions

Temperature
90 °C

Procedure

Dihydroxyacetone (65 g) was added slowly to liquid ammonia (250-300 ml), followed by ethyl propanimidate hydrochloride (65 g). The suspension was transferred to an autoclave and heated at 90° C. for 16 h. The ammonia was allowed to evaporate and then the reaction mixture concentrated in vacuo. The residue was dissolved in methanol, washed with charcoal, and then purified by chromatography, eluting with a gradient of System C (300:8:1 to 50:8:1). Trituration with acetone gave the title compound (29.83 g) as a white solid.

Workup

  1. customto evaporate
  2. concentrationthe reaction mixture concentrated in vacuo
  3. dissolutionThe residue was dissolved in methanol
  4. washwashed with charcoal
  5. custompurified by chromatography
  6. washeluting with a gradient of System C (300:8:1 to 50:8:1)

Sources & evidence

ORD record
ord-733ecc1595f34d02b3157dc0104e2bed
Source dataset
uspto-grants-1994_12
Patent number
US05374646

Reaction notes

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