Acetic Acid → HCID 178516151, compound

HRID 1725107Notes

Reaction equation

HRID 1725107 reaction equation
[F:1][C:2]([F:12])([F:11])[C:3](=O)[CH2:4][C:5]([O:7]CC)=O.C(O)(=O)C.[C:17]1([NH:23][NH2:24])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>O>[OH:7][C:5]1[N:23]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[N:24]=[C:3]([C:2]([F:1])([F:11])[F:12])[CH:4]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 7516PhenylhydrazineHCID 67793Ethyl 4,4,4-trifluoroacetoacetate

Product 1

HCID 178516151HCID 178516151, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Ethyl 4,4,4-trifluoroacetoacetate (18.4 g (0.1 mol)) was dissolved in 12.0 g (0.2 mol) of acetic acid. The resulting solution was cooled to 10° C. or less with stirring, and 11.8 g (0.11 mol) of phenylhydrazine was added dropwise thereto over 0.5 hours. After the dropwise addition, the solution was stirred at room temperature for 1 hour and subsequently at 80° C. for 5 hours. When the reaction was completed, the reaction solution was cooled to room temperature, and 100 mL of water was added thereto. The produced crystal was collected by filtration, washed twice with 50 mL of water and dried by a hot air drier to obtain 22.3 g (yield: 98.0%) of the title compound as a pale yellow crystal.

Workup

  1. temperatureThe resulting solution was cooled to 10° C. or less
  2. additionAfter the dropwise addition
  3. stirringthe solution was stirred at room temperature for 1 hour and subsequently at 80° C. for 5 hours
  4. filtrationThe produced crystal was collected by filtration
  5. washwashed twice with 50 mL of water
  6. customdried by a hot air drier

Sources & evidence

ORD record
ord-f4e5440d2ee44aeba66be2f24a774bbe
Source dataset
uspto-grants-2009_02
Patent number
US07488831B2

Reaction notes

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