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

HRID 372295Notes

Reaction equation

HRID 372295 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(N(CC)CC)C.[C:24](Cl)(=[O:31])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.C1(C)C(C)=CC=CC=1>C(Cl)(Cl)Cl>[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:24](=[O:31])[C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:6]1=[O:16]

Participants

6

Reactant 4

HCID 7237O-XyleneHCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 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 6212ChloroformSolvent

Procedure

Approximately 4.36 g. of 1-(2-methoxyethyl)-4-phenyl-4-imidazolin-2-one, 3 g. of triethylamine and 3 g. of benzoyl chloride are refluxed together for three hours in chloroform. The solution is cooled, washed with water, dried and the solvent removed to give an oil which is the O-benzoyl ester. The ester is refluxed for three hours in 20 ml. of xylene. The xylene is removed at reduced pressure. Recrystallization from ether gives the title compound as a pale yellow solid; m.p. 112°-117° C.

Workup

  1. temperatureThe solution is cooled
  2. washwashed with water
  3. customdried
  4. customthe solvent removed
  5. customto give an oil which
  6. customThe xylene is removed at reduced pressure
  7. customRecrystallization from ether

Sources & evidence

ORD record
ord-7662acb9c4b04705a5252769f3b8d4ae
Source dataset
uspto-grants-1978_05
Patent number
US04090025

Reaction notes

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