4-Methylbenzaldehyde → HCID 54007378, compound

HRID 1165692Notes

Reaction equation

HRID 1165692 reaction equation
C([N:4]1[CH2:8][C:7](=[O:9])[N:6]([C:10]2[CH:15]=[C:14]([F:16])[CH:13]=[CH:12][C:11]=2[F:17])[C:5]1=[O:18])(=O)C.[CH3:19][C:20]1[CH:27]=[CH:26][C:23]([CH:24]=O)=[CH:22][CH:21]=1.C(N(CC)CC)C>CN(C=O)C.O>[CH3:19][C:20]1[CH:27]=[CH:26][C:23]([CH:24]=[C:8]2[NH:4][C:5](=[O:18])[N:6]([C:10]3[CH:15]=[C:14]([F:16])[CH:13]=[CH:12][C:11]=3[F:17])[C:7]2=[O:9])=[CH:22][CH:21]=1

Participants

6

Reactant 3

HCID 77254-MethylbenzaldehydeHCID 8471TriethylamineHCID 14879182HCID 14879182, compound

Product 1

HCID 54007378HCID 54007378, compoundYield 89.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

N-acetyl-3-(2,5-difluorophenyl)imidazolidine-2,4-dione (2.1 g, 8.2 mmol), 4-methylbenzaldehyde (1.05 g, 8.7 mmol) and triethylamine (1.7 g, 16.5 mmol) were heated under reflux in DMF (20 mL) for 4 hours. The solution was cooled diluted with water and extracted with ethyl acetate (3×). The combined extracts were washed with brine (saturated), dried (over MgSO4), filtered and concentrated to give 2.3 grams of 5-(4-methylbenzylidene)-3-(2,5-difluorophenyl)imidazolidine-2,4-dione, m.p. 218°-224° C.

Workup

  1. temperatureThe solution was cooled
  2. extractionextracted with ethyl acetate (3×)
  3. washThe combined extracts were washed with brine (saturated)
  4. dry with materialdried (over MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-28e527c8e8b4416fb8338e5fcc8b714a
Source dataset
uspto-grants-1990_03
Patent number
US04911748

Reaction notes

Loading…