Water → 4-Methyl-1-trityl-1H-imidazole

HRID 1440387Notes

Reaction equation

HRID 1440387 reaction equation
[C:1]1([C:7](Cl)([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:21][C:22]1[N:23]=[CH:24][NH:25][CH:26]=1.C(N(CC)CC)C.O>CN(C=O)C>[CH3:21][C:22]1[N:23]=[CH:24][N:25]([C:7]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH:26]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6456Trityl chlorideHCID 8471TriethylamineHCID 178418800HCID 178418800, compound

Product 1

HCID 6182544-Methyl-1-trityl-1H-imidazole

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A suspension of triphenylmethyl chloride in anhydrous DMF (100 ml) was slowly added to a stirred solution of 4-methylimidazole (12.30 g) and triethylamine (41.8 ml) in anhydrous DMF (200 ml). After stirring the resultant slurry for ca. 3 h it was added to water (750 ml) and the solid removed by filtration. The solid was dissolved in dichloromethane (500 ml) and residual water separated. The organic solution was dried and evaporated to dryness to give the title compound as a white solid (42.7 g).

Workup

  1. customthe solid removed by filtration
  2. dissolutionThe solid was dissolved in dichloromethane (500 ml)
  3. customresidual water separated
  4. customThe organic solution was dried
  5. customevaporated to dryness

Sources & evidence

ORD record
ord-0b0dde02e5e84d9d9c768b4b8cdc469d
Source dataset
uspto-grants-1996_03
Patent number
US05498722

Reaction notes

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