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

HRID 2422378Notes

Reaction equation

HRID 2422378 reaction equation
[OH:1][CH2:2][C:3]1[N:4]=[CH:5][NH:6][CH:7]=1.[C:8]1([C:14](Cl)([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.CCN(C(C)C)C(C)C.O>CN(C=O)C>[C:14]([N:6]1[CH:7]=[C:3]([CH2:2][OH:1])[N:4]=[CH:5]1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)([C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1)[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6456Trityl chlorideHCID 81531DiisopropylethylamineHCID 178519868HCID 178519868, compound

Product 1

HCID 382182[1-(triphenylmethyl)-1H-imidazol-4-yl]methanolYield 99.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-hydroxymethylimidazole (4.53 g, 34 mmol) and triphenylmethylchloride (10.54 g, 38 mmol) were dissolved in DMF (50 mL). To this was added with stirring DIEA (13.46 g, 104 mmol) and the reaction mixture was stirred for 14 hrs. The reaction mixture was poured into water (750 mL) and stirred for about 30 min. The resulting solid was collected, washed with water (3×25 mL) and diisopropyl ether (3×25 mL), and dried in vacuo to yield 11.55 g (99%) of (1-trityl-1H-imidazol-4-yl)methanol. Purity (HPLC): 93%; retention time, 6.37 min.; column: Phenomenex Luna C18(2) (5 μm, 50×4.6 mm); gradient: 10% to 100% B in A over 10 min. at 1.25 mL/min. Solvent A: 0.1% TFA in water, Solvent B: 0.1% TFA in AcCN. ES-MS: (M+H)+=341.1.

Workup

  1. stirringstirred for about 30 min
  2. customThe resulting solid was collected
  3. washwashed with water (3×25 mL) and diisopropyl ether (3×25 mL)
  4. customdried in vacuo

Sources & evidence

ORD record
ord-77dfcdfe3d6c4d0ba741329080ab15e4
Source dataset
uspto-grants-2011_06
Patent number
US07960349B2

Reaction notes

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