Trifluoroacetic acid → 2,2,2-Trifluoro-N'-(trifluoroacetyl)acetohydrazide

HRID 1797763Notes

Reaction equation

HRID 1797763 reaction equation
[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=O.[F:8][C:9]([F:15])([F:14])[C:10]([NH:12][NH2:13])=[O:11]>C1C=CC=CC=1>[F:8][C:9]([F:15])([F:14])[C:10]([NH:12][NH:13][C:3](=[O:5])[C:2]([F:7])([F:6])[F:1])=[O:11]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 229753Trifluoroacetohydrazide

Product 1

HCID 2297542,2,2-Trifluoro-N'-(trifluoroacetyl)acetohydrazide

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

Trifluoroacetic acid (7.6 mL, 0.1 mol) was added to a stirred solution of trifluoroacethydrazide (12.8 g, 0.1 mol) in benzene (100 mL) and the mixture was heated under reflux for 2 h. A Dean and Stark trap was fitted, and reflux was continued for 3 h. Reflux was continued in the absence of the Dean and Stark trap (3 h) and then with the trap refitted (20 h). The resulting white solid was collected by filtration, dried in vacuum and identified as 1,2-bis(trifluoroacetyl)hydrazine (16.5 g, 73%). M.p. 173-175° C.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 2 h
  3. customA Dean and Stark trap was fitted
  4. temperaturereflux
  5. temperatureReflux
  6. customwas continued in the absence of the Dean and Stark trap (3 h)
  7. custom(20 h)
  8. filtrationThe resulting white solid was collected by filtration
  9. customdried in vacuum

Sources & evidence

ORD record
ord-0fbc5c7f57904aa7b5dc0e5c6e36a6ea
Source dataset
uspto-grants-2013_01
Patent number
US08343260B2

Reaction notes

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