Water → 1-Triphenylmethyl-4-methyl-5-hydroxymethylimidazole

HRID 2072797Notes

Reaction equation

HRID 2072797 reaction equation
Cl.[OH:2][CH2:3][C:4]1[N:5]=[CH:6][NH:7][C:8]=1[CH3:9].C(N(CC)CC)C.[C:17](Cl)([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.O>CN(C)C=O>[C:18]1([C:17]([C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)([C:30]2[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=2)[N:5]2[C:4]([CH2:3][OH:2])=[C:8]([CH3:9])[N:7]=[CH:6]2)[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6456Trityl chlorideHCID 8471TriethylamineHCID 30847074-Methylimidazol-5-ylmethanolhydrochloride

Product 1

HCID 212245551-Triphenylmethyl-4-methyl-5-hydroxymethylimidazoleYield 49.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 19 g of 4-hydroxymethyl-5-methylimidazole hydrochloride in 350 ml of dimethylformamide was added 36 ml of triethylamine followed in 10 minutes by the addition of 35 g of trityl chloride. A water bath was used to cool the reaction mixture such that it did not rise above 36° C. After stirring at room temperature for 4 hours, the mixture was poured into 1 liter of water and ice. The resulting precipitate was filtered and washed with acetone (2×250 ml) to give 22 g of product.

Workup

  1. customA water bath was used
  2. temperatureto cool the reaction mixture such that it
  3. customdid not rise above 36° C
  4. filtrationThe resulting precipitate was filtered
  5. washwashed with acetone (2×250 ml)

Sources & evidence

ORD record
ord-4ae091fd0a714b769b55cad1b73dfb59
Source dataset
uspto-grants-1990_04
Patent number
US04914207

Reaction notes

Loading…