Water → HCID 11378721, compound

HRID 848236Notes

Reaction equation

HRID 848236 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-deedc35eaeb648e38985a711064f2a4c
Source dataset
uspto-grants-1981_10
Patent number
US04294973

Reaction notes

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