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

HRID 2306165Notes

Reaction equation

HRID 2306165 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 dry DMF (250 mL) at room temperature was added triethylamine (90.6 mL, 650 mmol). A white solid precipitated from the solution. Chlorotriphenyl-methane (76.1 g, 273 mmol) in DMF (500 mL) was added dropwise. The reaction mixture was stirred for 20 hours, poured over ice, filtered, and washed with ice water. The resulting product was slurried with cold dioxane, filtered, and dried in vacuo to provide the titled product as a white solid.

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-49331124b64d42599989ff9051d70e8c
Source dataset
uspto-grants-2002_08
Patent number
US06441017B1

Reaction notes

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