Water → HCID 11378721, compound

HRID 1732784Notes

Reaction equation

HRID 1732784 reaction equation
[C:1]([N:4]1[CH:8](Cl)[CH:7](Cl)[N:6]([C:11](=[O:13])[CH3:12])[C:5]1=[O:14])(=[O:3])[CH3:2].CN(C)C=O.O>C(OCC)C.[Zn]>[C:11]([N:6]1[CH:7]=[CH:8][N:4]([C:1](=[O:3])[CH3:2])[C:5]1=[O:14])(=[O:13])[CH3:12]

Participants

6

Reactant 3

HCID 962WaterHCID 6228DimethylformamideHCID 12514014HCID 12514014, compound

Product 1

HCID 11378721HCID 11378721, compoundYield 95.2%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalyst2×HCID 3283Diethyl EtherSolvent

Procedure

Activated zinc (from 63.5 g (1.0 mol) of zinc), prepared in accordance with J.Org.Chem. 29, 2049 (1964), are added in portions to a boiling solution of 119.5 g (0.5 mol) of recrystallised 1,3-diacetyl-4,5-dichloro-imidazolidin-2-one and 8 ml of dimethylformamide in 400 ml of dry diethyl ether and the mixture is heated under reflux until conversion is complete (16 hours). After the reaction solution has cooled, 200 ml of water are added to it, and the mixture is filtered. The filter cake is washed with 3×100 ml of benzene and the organic phases are combined and washed until they give a neutral reaction. Drying over sodium sulphate and evaporation gives 80.0 g (about 95%) of 1,3-diacetyl-4-imidazolin-2-one of melting point 106° C., identical with a sample prepared independently in accordance with J.Amer.Chem. Soc. 54, 3413 (1932).

Workup

  1. temperaturethe mixture is heated
  2. temperatureunder reflux until conversion
  3. custom(16 hours)
  4. temperatureAfter the reaction solution has cooled
  5. filtrationthe mixture is filtered
  6. washThe filter cake is washed with 3×100 ml of benzene
  7. washwashed until they
  8. customgive
  9. customa neutral reaction
  10. dry with materialDrying over sodium sulphate and evaporation

Sources & evidence

ORD record
ord-a4695f0374c6408883bd6f0fe2c98fff
Source dataset
uspto-grants-1980_12
Patent number
US04238618

Reaction notes

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