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

HRID 278173Notes

Reaction equation

HRID 278173 reaction equation
Cl.[NH:2]1[CH:6]=[C:5]([CH2:7][C:8]([O:10][CH3:11])=[O:9])[N:4]=[CH:3]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>[C:19]1([C:25]([C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)([C:32]2[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=2)[N:2]2[CH:6]=[C:5]([CH2:7][C:8]([O:10][CH3:11])=[O:9])[N:4]=[CH:3]2)[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 11692BromotriphenylmethaneHCID 178499561HCID 178499561, compound

Product 1

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

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of methyl imidazol-4-ylacetate hydrochloride from Step A (4.30 g, 24.3 mmol) in dry DMF (50 mL) under argon were added triethylamine (5.41 g, 53.5 mmol) and triphenylmethyl bromide (8.64 g, 26.7 mmol). The reaction mixture was stirred at ambient temperature overnight, then partitioned between water (250 mL) and EtOAc (250 mL). The organic layer was dried over Na2SO4, filtered, and concentrated under reduced pressure. The residue was purified by flash column chromatography, eluting with 50% hexane in EtOAc to remove nonpolar impurities, then EtOAc to elute the titled product as a white solid.

Workup

  1. custompartitioned between water (250 mL) and EtOAc (250 mL)
  2. dry with materialThe organic layer was dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by flash column chromatography
  6. washeluting with 50% hexane in EtOAc
  7. customto remove nonpolar impurities
  8. washEtOAc to elute the titled product as a white solid

Sources & evidence

ORD record
ord-f783beca151b411bb8e66ec3babcf837
Source dataset
uspto-grants-2002_03
Patent number
US06358985B1

Reaction notes

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