Benzoyl chloride → 3-Benzoyl-1-(2-methoxyethyl)-4-phenyl-1,3-dihydro-2H-imidazol-2-one

HRID 372296Notes

Reaction equation

HRID 372296 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][N:5]1[CH:9]=[C:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[NH:7][C:6]1=[O:16].[C:17](Cl)(=[O:24])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.C(N(CCCC)CCCC)CCC>C1(C)C(C)=CC=CC=1>[CH3:1][O:2][CH2:3][CH2:4][N:5]1[CH:9]=[C:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[N:7]([C:17](=[O:24])[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:6]1=[O:16]

Participants

5

Reactant 3

HCID 7412Benzoyl chlorideHCID 7622TributylamineHCID 12803422HCID 12803422, compound

Product 1

HCID 128034393-Benzoyl-1-(2-methoxyethyl)-4-phenyl-1,3-dihydro-2H-imidazol-2-one

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

Approximately 21.8 g. of 1-(2-methoxyethyl)-4-phenyl-4-imidazolin-2-one, 14.5 g. of benzoyl chloride and 20 g. of tri-n-butylamine are refluxed together in 60 ml. of xylene for sixteen hours. The solvent is distilled off under reduced pressure and the remaining viscous oil is dissolved in 300 ml. of benzene. The benzene solution is washed with water (2×100 ml.), dried over sodium sulfate, and the solvent removed to give a semisolid. Recrystallization from ether gives the title compound as a pale yellow solid; m.p. 114°-117° C.

Workup

  1. distillationThe solvent is distilled off under reduced pressure
  2. dissolutionthe remaining viscous oil is dissolved in 300 ml
  3. washThe benzene solution is washed with water (2×100 ml.)
  4. dry with materialdried over sodium sulfate
  5. customthe solvent removed
  6. customto give a semisolid
  7. customRecrystallization from ether

Sources & evidence

ORD record
ord-045e3e86c4984e578d088a70ea0ea2f1
Source dataset
uspto-grants-1978_05
Patent number
US04090025

Reaction notes

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