Trityl chloride → methyl 1-trityl-1H-imidazole-4-carboxylate

HRID 2355286Notes

Reaction equation

HRID 2355286 reaction equation
C(N(CC)CC)C.[CH3:8][O:9][C:10]([C:12]1[N:13]=[CH:14][NH:15][CH:16]=1)=[O:11].[C:17]1([C:23](Cl)([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>C(#N)C>[CH3:8][O:9][C:10]([C:12]1[N:13]=[CH:14][N:15]([C:23]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=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:16]=1)=[O:11]

Participants

5

Reactant 3

HCID 6456Trityl chlorideHCID 8471TriethylamineHCID 178418785HCID 178418785, compound

Product 1

HCID 10429115methyl 1-trityl-1H-imidazole-4-carboxylateYield 95.8%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Add triethylamine (1.88 mL, 13.48 mmol) to a mixture of methyl-4-imidazolecarboxylate (1.0 g, 7.93 mmol) and triphenylmethyl chloride (2.43 g, 8.72 mmol) in anhydrous acetonitrile (25 mL) over 10 min at room temperature and stir overnight. Quench with water and extract with ethyl acetate (3×). Combine the organic layers, wash with 1N hydrochloride solution, water, saturated aqueous sodium bicarbonate solution and brine sequentially, dry over sodium sulfate, and concentrate to provide the title compound 1-trityl-1H-imidazole-4-carboxylic acid methyl ester (2.8 g, 7.60 mmol).

Workup

  1. customQuench with water
  2. extractionextract with ethyl acetate (3×)
  3. washCombine the organic layers, wash with 1N hydrochloride solution, water, saturated aqueous sodium bicarbonate solution and brine sequentially
  4. dry with materialdry over sodium sulfate
  5. concentrationconcentrate

Sources & evidence

ORD record
ord-dd79221a6b6340fda362df06c82c00f2
Source dataset
uspto-grants-2010_07
Patent number
US07754742B2

Reaction notes

Loading…