Triethylamine → 1-(triphenylmethyl)-1H-Imidazole-4-acetic acid methyl ester

HRID 1068402Notes

Reaction equation

HRID 1068402 reaction equation
Cl.[CH3:2][O:3][C:4](=[O:11])[CH2:5][C:6]1[N:7]=[CH:8][NH:9][CH:10]=1.C(N(CC)CC)C.[C:19]1([C:25](Br)([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>CN(C=O)C.CCOC(C)=O.O>[CH3:2][O:3][C:4](=[O:11])[CH2:5][C:6]1[N:7]=[CH:8][N:9]([C:25]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)([C:32]2[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=2)[C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)[CH:10]=1

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 11692BromotriphenylmethaneHCID 178499561HCID 178499561, compound

Product 1

HCID 105239671-(triphenylmethyl)-1H-Imidazole-4-acetic acid methyl ester

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of the product from Step A (24.85 g, 0.141 mol) in DMF (115 ml) was added triethylamine (57.2 ml, 0.412 mol) and triphenylmethyl bromide (55.3 g, 0.171 mol) and the suspension was stirred for 24 hrs. After this time, the reaction mixture was diluted with EtOAc and water. The organic phase was washed with saturated aqueous NaHCO3, dried (Na2SO4) and the solvent evaporated in vacuo. The residue was purified by chromatography (SiO2, gradient elution, 0-100% EtOAc in hexanes;) to provide the title compound as a white solid.

Workup

  1. washThe organic phase was washed with saturated aqueous NaHCO3
  2. dry with materialdried (Na2SO4)
  3. customthe solvent evaporated in vacuo
  4. customThe residue was purified by chromatography (SiO2, gradient elution, 0-100% EtOAc in hexanes;)

Sources & evidence

ORD record
ord-0dd57115ea7946e8a099e94d4db6e59b
Source dataset
uspto-grants-2001_06
Patent number
US06248756B1

Reaction notes

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