Hydrochloric Acid → 1,3-Dihydro-4-methyl-5-(2-phenylacetyl)-2H-imidazol-2-one

HRID 543897

Reaction equation

HRID 543897 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[CH3:5][C:6]1[NH:7][C:8](=[O:11])[NH:9][CH:10]=1.[C:12]1([CH2:18][C:19](Cl)=[O:20])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.Cl>ClCCl>[CH3:5][C:6]1[NH:7][C:8](=[O:11])[NH:9][C:10]=1[C:19](=[O:20])[CH2:18][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7679Phenylacetyl chlorideHCID 709351,3-dihydro-4-methyl-2H-imidazol-2-oneHCID 6451240Aluminum(III) Chloride

Product 1

HCID 130720101,3-Dihydro-4-methyl-5-(2-phenylacetyl)-2H-imidazol-2-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 26.6 g (0.2 mole) of aluminum chloride in 250 ml of dichloromethane is added 9.8 g (0.1 mole) of 1,3-dihydro-4-methyl-2H-imidazol-2-one and, dropwise, 16.9 g (0.11 mole) of phenylacetyl chloride. The mixture is stirred and heated to reflux for 5 hours. The mixture is cooled and 200 ml of 2N-hydrochloric acid is added dropwise. The resulting precipitate is collected, washed with water, and recrystallized for 50% aqueous ethanol to give the title compound, m.p. 239°-240° C.

Workup

  1. temperatureheated
  2. temperatureto reflux for 5 hours
  3. temperatureThe mixture is cooled
  4. customThe resulting precipitate is collected
  5. washwashed with water
  6. customrecrystallized for 50% aqueous ethanol

Sources & evidence

ORD record
ord-794845417e3b415ca1d2a84de45cfb27
Source dataset
uspto-grants-1984_05
Patent number
US04447619

Linked notes

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