Imidazole → 1H-Imidazole-1-acetic acid, phenylmethyl ester

HRID 847632Notes

Reaction equation

HRID 847632 reaction equation
[NH:1]1[CH:5]=[CH:4][N:3]=[CH:2]1.Br[CH2:7][C:8]([O:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:9]>ClCCl>[N:1]1([CH2:7][C:8]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[O:9])[CH:5]=[CH:4][N:3]=[CH:2]1

Participants

4

Reactant 2

HCID 795ImidazoleHCID 62576Benzyl bromoacetate

Product 1

HCID 100362471H-Imidazole-1-acetic acid, phenylmethyl esterYield 89.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 1.4 g (21 mmol) of imidazole and 1.0 ml (6.3 mmol) of benzyl 2-bromoacetate in 40 ml of dichloromethane was stirred at ambient temperature for 16 h. The resulting solution was washed with water, dried over Na2SO4, and concentrated in vacuo. Silica gel chromatography of the residue using 5% methanol in chloroform provided 1.22 g (89%) of the desired compound as an oil. 1H NMR (CDCl3) δ 4.73 (s, 2H), 5.21 (s, 2H), 6.96 (t, J=1 Hz, 1H), 7.11 (t, J=1 Hz, 1H), 7.36 (m, 5H), 7.51 (br s, 1H).

Workup

  1. washThe resulting solution was washed with water
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ffea8a4f0f6e45a3b1977e91075cad31
Source dataset
uspto-grants-1992_08
Patent number
US05142056

Reaction notes

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