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

HRID 1418077Notes

Reaction equation

HRID 1418077 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 dry DMF (250 mL) 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 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 which was 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-7666c623417040b0a8d75016d2ea852d
Source dataset
uspto-grants-1999_03
Patent number
US05880140

Reaction notes

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