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

HRID 267089

Reaction equation

HRID 267089 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)C=O.C(OCC)(=O)C.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 dimethyl formamide (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 hr. After this time, the reaction mixture was diluted with ethyl acetate (EtOAc) (1 l) and water (350 ml). The organic phase was washed with sat. aq. NaHCO3 (350 ml), dried (Na2SO4) and evaporated in vacuo. The residue was purified by flash chromatography (SiO2, 0-100% ethyl acetate in hexanes; gradient elution) to provide the title compound as a white solid.

Workup

  1. washThe organic phase was washed with sat. aq. NaHCO3 (350 ml)
  2. dry with materialdried (Na2SO4)
  3. customevaporated in vacuo
  4. customThe residue was purified by flash chromatography (SiO2, 0-100% ethyl acetate in hexanes; gradient elution)

Sources & evidence

ORD record
ord-e9a6038ca5c2408c834d0128c4ebb3d7
Source dataset
uspto-grants-1997_07
Patent number
US05652257

Linked notes

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