HCID 13755489, compound → 1-(4-Oxocyclohexyl)imidazolidin-2-one

HRID 979903Notes

Reaction equation

HRID 979903 reaction equation
N[CH:2]1[CH2:7][CH2:6][CH:5]([N:8]2[CH2:12][CH2:11][NH:10][C:9]2=[O:13])[CH2:4][CH2:3]1.Cl[O-:15].[K+]>[Cl-].C([N+](CCCC)(CCCC)CCCC)C1C=CC=CC=1.C(OCC)(=O)C>[O:15]=[C:2]1[CH2:7][CH2:6][CH:5]([N:8]2[CH2:12][CH2:11][NH:10][C:9]2=[O:13])[CH2:4][CH2:3]1

Participants

5

Reactant 2

HCID 13755489HCID 13755489, compoundHCID 23665762Potassium hypochlorite

Product 1

HCID 202230821-(4-Oxocyclohexyl)imidazolidin-2-one

Reagents, catalysts & solvents 2

HCID 159952Benzyltributylammonium chlorideCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 18.3 g of 1-(4-aminocyclohexyl)-2-imidazolidinone as a mixture of cis and trans isomers, 2.0 g of benzyltributylammonium chloride, 250 ml of ethyl acetate and 360 ml of an aqueous 10% potassium hypochlorite solution [according to methodology as described by C. A. Meyers, J. Org. Chem. 26, 1046 (1961)] is stirred at room temperature for 11/2 hours. The organic layer is separated and the aqueous layer is extracted with ethyl acetate. The pooled organic phases are washed with water, sodium bicarbonate solution and dilute hydrochloric acid, then dried and evaporated to dryness to yield 1-(4-oxocyclohexyl)-2-imidazolidinone.

Workup

  1. customThe organic layer is separated
  2. extractionthe aqueous layer is extracted with ethyl acetate
  3. washThe pooled organic phases are washed with water, sodium bicarbonate solution and dilute hydrochloric acid
  4. customdried
  5. customevaporated to dryness

Sources & evidence

ORD record
ord-9fd8a531d3e44da2bc425bc004f22739
Source dataset
uspto-grants-1987_01
Patent number
US04634713

Reaction notes

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