Trityl chloride → [1-(triphenylmethyl)-1H-imidazol-4-yl]methanol

HRID 1739006Notes

Reaction equation

HRID 1739006 reaction equation
Cl.[OH:2][CH2:3][C:4]1[N:5]=[CH:6][NH:7][CH:8]=1.C(N(CC)CC)C.Cl[C:17]([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>CN(C=O)C>[OH:2][CH2:3][C:4]1[N:5]=[CH:6][N:7]([C:17]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)([C:30]2[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=2)[C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)[CH:8]=1

Participants

5

Reactant 3

HCID 6456Trityl chlorideHCID 8471TriethylamineHCID 178418488HCID 178418488, compound

Product 1

HCID 382182[1-(triphenylmethyl)-1H-imidazol-4-yl]methanol

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a solution of 4-(hydroxymethyl)imidazole hydrochloride (35.0 g, 260 mmol) in 250 mL of dry DMF at room temperature is added triethylamine (90.6 mL, 650 mmol). A white solid precipitated from the solution. Chlorotriphenylmethane (76.1 g, 273 mmol) in 500 mL of DMF is added dropwise. The reaction mixture is stirred for 20 hours, poured over ice, filtered, and washed with ice water. The resulting product is slurried with cold dioxane, filtered, and dried in vacuo to provide the titled product as a white solid which is sufficiently pure for use in the next step.

Workup

  1. customA white solid precipitated from the solution
  2. additionpoured over ice
  3. filtrationfiltered
  4. washwashed with ice water
  5. filtrationfiltered
  6. customdried in vacuo

Sources & evidence

ORD record
ord-7a3e12a5cb25406a9bf297b65a6051fb
Source dataset
uspto-grants-1999_10
Patent number
US05965578

Reaction notes

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