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

HRID 6771

Reaction equation

HRID 6771 reaction equation
Cl.[OH:2][CH2:3][C:4]1[N:5]=[CH:6][NH:7][CH:8]=1.CCN(CC)CC.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, compound2×

Product 1

HCID 382182[1-(triphenylmethyl)-1H-imidazol-4-yl]methanolYield 78.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

4-Hydroxymethylimidazole hydrochloride (compound xiii where R2 is H) (2.50 g, 18.6 mmol) and Et3N (2.59 ml, 18.6 mmol) were combined in DMF (30 ml) and stirred at room temperature. A solution of chlorotriphenylmethane (5.19 g, 18.6 mmol) in DMF (25 ml) was added dropwise at room temperature and the resulting mixture was stirred at room temperature for about 23 hours and then poured into ice water (300 ml). The product was filtered off, washed with cold water (75 ml) and triturated with p-dioxane (30 ml). The product was filtered off and dried under reduced pressure to yield product (4.96 g, 78%). NMR (300 MHZ, DMSO-d6, 30° C.) 7.3–7.5 (9H, m), 7.25–7.35 (1H, d), 7.0–7.2 (6H, m), 6.7–6.75 (1H, s), 4.15–4.2 (2H, m).

Workup

  1. stirringthe resulting mixture was stirred at room temperature for about 23 hours
  2. filtrationThe product was filtered off
  3. washwashed with cold water (75 ml)
  4. customtriturated with p-dioxane (30 ml)
  5. filtrationThe product was filtered off
  6. customdried under reduced pressure

Sources & evidence

ORD record
ord-6cbd47be74554fafb353de8fa6d07f48
Source dataset
uspto-grants-2006_08
Patent number
US07084135B1

Linked notes

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