Hydrazine → 3,4,4-Trifluoro-3-butenoic acid, 2-(3,4,4-trifluoro-1-oxo-3-butenyl)hydrazide

HRID 54734

Reaction equation

HRID 54734 reaction equation
[F:1][C:2](=[C:7]([F:9])[F:8])[CH2:3][C:4](Cl)=[O:5].[NH2:10][NH2:11]>CCOCC>[F:1][C:2](=[C:7]([F:9])[F:8])[CH2:3][C:4]([NH:10][NH:11][C:4](=[O:5])[CH2:3][C:2]([F:1])=[C:7]([F:9])[F:8])=[O:5]

Participants

4

Reactant 2

HCID 9321HydrazineHCID 109207893,4,4-Trifluoro-3-butenoyl chloride

Product 1

HCID 152391913,4,4-Trifluoro-3-butenoic acid, 2-(3,4,4-trifluoro-1-oxo-3-butenyl)hydrazideYield 52.8%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
-78 °C

Procedure

A solution of 3,4,4-trifluoro-3-butenoyl chloride (2.4 g, 0.0151 mole) in dry ether (20 mL) is treated dropwise with anhydrous hydrazine (0.48 g, 0.15 mole) with stirring at -78° C. The mixture is allowed to reach room temperature and the white precipitate is filtered and dissolved in ethyl acetate. The ethyl acetate solution is washed with 5% sodium bicarbonate and dried. Evaporation of the solvent gave 1.1 g of the desired product as a white solid, a 47% yield. m.p. 191°-193° C.

Workup

  1. customto reach room temperature
  2. filtrationthe white precipitate is filtered
  3. dissolutiondissolved in ethyl acetate
  4. washThe ethyl acetate solution is washed with 5% sodium bicarbonate
  5. customdried
  6. customEvaporation of the solvent

Sources & evidence

ORD record
ord-6fb135ed53aa4248ac253ded8765f72a
Source dataset
uspto-grants-1997_04
Patent number
US05623084

Linked notes

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