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

HRID 342123Notes

Reaction equation

HRID 342123 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>C(Cl)Cl>[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

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 6344DichloromethaneSolvent

Procedure

To a suspension of the product from Step A (7.49 g, 42.4 mmol) in methylene chloride (200 ml) was added triethylamine (17.7 ml, 127 mmol) and triphenylmethyl bromide(16.4 g, 50.8 mmol) and stirred for 72 h. After this time, the reaction mixture was washed with sat. aq. NaHCO3 (100 ml) and water (100 ml). The organic layer was evaporated in vacuo and the residue was purified by flash chromatography(30-100% ethyl acetate in hexanes gradient elution) to provide the title compound as a white solid. 1H NMR(CDCl3, 400 MHz) δ 7.35(1H, s), 7.31(9H, m), 7.22(6H, m), 6.76(1H, s), 3.68(3H, s) and 3.60(2H, s) ppm.

Workup

  1. washAfter this time, the reaction mixture was washed with sat. aq. NaHCO3 (100 ml) and water (100 ml)
  2. customThe organic layer was evaporated in vacuo
  3. customthe residue was purified by flash chromatography(30-100% ethyl acetate in hexanes gradient elution)

Sources & evidence

ORD record
ord-646ebf3bd87e405fb4aa4bdf71d25b6c
Source dataset
uspto-grants-1999_01
Patent number
US05856326

Reaction notes

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