Cyclohexene oxide → HCID 19973446, compound

HRID 1757110Notes

Reaction equation

HRID 1757110 reaction equation
[CH:1]12[O:7][CH:2]1[CH2:3][CH2:4][CH2:5][CH2:6]2.C(=O)([O-])[O-].[K+].[K+].[N+:14]([C:17]1[N:18]=[CH:19][NH:20][CH:21]=1)([O-:16])=[O:15]>CN(C)C=O.C(Cl)(Cl)Cl>[N+:14]([C:17]1[N:18]=[CH:19][N:20]([CH:2]2[CH2:3][CH2:4][CH2:5][CH2:6][CH:1]2[OH:7])[CH:21]=1)([O-:16])=[O:15]

Participants

6

Reactant 3

HCID 9246Cyclohexene oxideHCID 11430Potassium CarbonateHCID 178526856HCID 178526856, compound

Product 1

HCID 19973446HCID 19973446, compoundYield 63.8%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

40.0 ml (395 mmol) of cyclohexene oxide and 86.37 g (625 mmol) of potassium carbonate were added to a suspension of 50.08 g (443 mmol) of 4-nitroimidazole in 800 ml of N,N-dimethylformamide. The obtained mixture was stirred under heating at 100° C. for 3 days and 20 hours to give a yellowish-brown suspension. This suspension was cooled by allowing to stand, and filtered to remove insolubles. The filtrate was concentrated in a vacuum. Water was added to the obtained residue to form a crystalline precipitate. This crystalline precipitate was recovered by filtration and washed with water. The obtained crude crystal was dissolved in chloroform and the obtained solution was washed with a saturated aqueous solution of common salt. The organic phase was dried over anhydrous magnesium sulfate and concentrated in a vacuum. In the course of the concentration, a crystal began to precipitate. This crystal was recovered by filtration to give 53.26 g of the title compound as a colorless crystal. Further, the filtrate was recrystallized from dichloromethane/diisopropyl ether to give 5.14 g of the title compound as a light-brown crystal. Thus, 58.30 g of the title compound was obtained in total (yield: 70%).

Workup

  1. customto give a yellowish-brown suspension
  2. temperatureThis suspension was cooled
  3. filtrationfiltered
  4. customto remove insolubles
  5. concentrationThe filtrate was concentrated in a vacuum
  6. additionWater was added to the obtained residue
  7. customto form a crystalline precipitate
  8. filtrationThis crystalline precipitate was recovered by filtration
  9. washwashed with water
  10. customThe obtained crude crystal
  11. washthe obtained solution was washed with a saturated aqueous solution of common salt
  12. dry with materialThe organic phase was dried over anhydrous magnesium sulfate
  13. concentrationconcentrated in a vacuum
  14. concentrationIn the course of the concentration
  15. customto precipitate
  16. filtrationThis crystal was recovered by filtration

Sources & evidence

ORD record
ord-d3b8050a6ad042999819f02196480b14
Source dataset
uspto-grants-1995_08
Patent number
US05444066

Reaction notes

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