Cyclohexanecarboxaldehyde → HCID 57222144, compound

HRID 1165694Notes

Reaction equation

HRID 1165694 reaction equation
CC(C)([O-])C.[K+].C([N:10]1[CH2:14][C:13](=[O:15])[N:12]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[F:22])[C:11]1=[O:23])(=O)C.[CH:24]1([CH:30]=O)[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]1>CN(C=O)C.O>[CH:24]1([CH:30]=[C:14]2[NH:10][C:11](=[O:23])[N:12]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[F:22])[C:13]2=[O:15])[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]1

Participants

6

Reactant 3

HCID 16275CyclohexanecarboxaldehydeHCID 22166031HCID 22166031, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 57222144HCID 57222144, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Potassium tert-butoxide (1.12 g, 10.0 mmol) was added in one portion to a solution of N-acetyl-3-(2-fluorophenyl)imidazolidine-2,4-dione (2.36 g, 10.0 mmol) and cyclohexanecarboxaldehyde (1.23 g, 11.0 mmol) in DMF (10 mL) at 0° C. The solution was allowed to warm to RT overnight with stirring, then diluted with water and extracted with ethyl acetate. The combined extracts were washed with brine (saturated), dried (over MgSO4), filtered and concentrated. The crude product was recrystallized from hexane/ethyl acetate to give 5-cyclohexylmethylene-3-(2-fluorophenyl)imidazolidine-2,4-dione, as a white solid.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe combined extracts were washed with brine (saturated)
  3. dry with materialdried (over MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude product was recrystallized from hexane/ethyl acetate

Sources & evidence

ORD record
ord-b66b05039cc0450a88aa646e65897f7f
Source dataset
uspto-grants-1990_03
Patent number
US04911748

Reaction notes

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