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

HRID 379041Notes

Reaction equation

HRID 379041 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>[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:7]2[CH:8]=[C:4]([CH2:3][OH:2])[N:5]=[CH:6]2)[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=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 was 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 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 title product as a white.

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-08ba8f8a7f334e99bf55e8d6a083d96a
Source dataset
uspto-grants-2001_10
Patent number
US06297239B1

Reaction notes

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