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

HRID 1390690Notes

Reaction equation

HRID 1390690 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-81d54a3ab2b248588cd7e117fec6d91e
Source dataset
uspto-grants-1979_02
Patent number
US04139707

Reaction notes

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