Triethylamine → HCID 53748986, compound

HRID 1032472Notes

Reaction equation

HRID 1032472 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.[F:19][C:20]1[CH:27]=[CH:26][CH:25]=[CH:24][C:21]=1[CH:22]=O.C(N(CC)CC)C>CN(C=O)C.O>[F:19][C:20]1[CH:27]=[CH:26][CH:25]=[CH:24][C:21]=1[CH:22]=[C:8]1[NH:4][C:5](=[O:18])[N:6]([C:10]2[CH:15]=[C:14]([F:16])[CH:13]=[CH:12][C:11]=2[F:17])[C:7]1=[O:9]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 67970o-FluorobenzaldehydeHCID 14879182HCID 14879182, compound

Product 1

HCID 53748986HCID 53748986, compoundYield 50.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

N-acetyl-3-(2,5-difluorophenyl)imidazolidine-2,4dione (2.29 g, 8.65 mmol), 2-fluorobenzaldehyde (1.13 g, 9.1 mmol) and triethylamine (1.75 g, 17.3 mmol) were heated under reflux in DMF (15 mL) for 3 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, concentrated, and purified by column chromatography to give 1.4 grams of 5-(2-fluorobenzylidene)-3-(2,5-difluorophenyl)imidazolidine-2,4-dione, m.p. 180°-183° 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
  7. custompurified by column chromatography

Sources & evidence

ORD record
ord-506dff041fac4492a4a0a1f50a12551a
Source dataset
uspto-grants-1990_09
Patent number
US04958028

Reaction notes

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