Formaldehyde → 1-Benzyl-4,5-dimethyl-2-hydroxymethylimidazole

HRID 65042Notes

Reaction equation

HRID 65042 reaction equation
[CH2:1]([N:8]1[C:12]([CH3:13])=[C:11]([CH3:14])[N:10]=[CH:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:15]=[O:16]>>[CH2:1]([N:8]1[C:12]([CH3:13])=[C:11]([CH3:14])[N:10]=[C:9]1[CH2:15][OH:16])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 712FormaldehydeHCID 122042631-Benzyl-4,5-dimethylimidazole

Product 1

HCID 202350581-Benzyl-4,5-dimethyl-2-hydroxymethylimidazole

Conditions

Temperature
150 °C

Procedure

A mixture of 8 g (43 mmol) of 1-benzyl-4,5-dimethylimidazole and 60 ml of 40% aqueous formaldehyde solution was heated in a sealed autoclave at 150° C. for 20 hours. The mixture was evaporated and the semi-solid residue was chromatographed on a column of 300 g of silica gel using a 20% solution of methanol in chloroform for the elution. Evaporation of the eluate yielded 6 g of 1-benzyl-4,5-dimethyl-2-hydroxymethylimidazole of melting point 156°-158° C. After recrystallization from methylcyclohexane, the melting point was 160°-162° C. A portion of the product was treated with a solution of hydrogen chloride in ethanol. Addition of diethyl ether precipitated 1-benzyl-4,5-dimethyl-2-hydroxymethylimidazole hydrochloride of melting point 162°-163° C.

Workup

  1. customThe mixture was evaporated
  2. customthe semi-solid residue was chromatographed on a column of 300 g of silica gel using a 20% solution of methanol in chloroform
  3. washfor the elution
  4. customEvaporation of the

Sources & evidence

ORD record
ord-f2befbde95164f2fb1507a2cf563d208
Source dataset
uspto-grants-1986_09
Patent number
US04612324

Reaction notes

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