Hydrazine hydrate (1:1) → 3,3,3-Trifluoropropanehydrazide

HRID 1786180Notes

Reaction equation

HRID 1786180 reaction equation
C[O:2][C:3](=O)[CH2:4][C:5]([F:8])([F:7])[F:6].O.[NH2:11][NH2:12]>CO>[F:6][C:5]([F:8])([F:7])[CH2:4][C:3]([NH:11][NH2:12])=[O:2]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 2782392Methyl 3,3,3-trifluoropropanoate

Product 1

HCID 167866073,3,3-TrifluoropropanehydrazideYield 58%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 3,3,3-trifluoro-propionic acid methyl ester (24.6 g, 173 mmol) in methanol (173 mL) was treated with hydrazine hydrate (8.4 mL, 173 mmol). The resulting mixture was then heated under reflux for 16 h and filtered. The filtrate was adsorbed on silica, evaporated and chromatographed (SiO2, dichloromethane:methanol=95:5 to 90:10). The title compound (14.2 g, 58%) was obtained as a white solid. MS: m/e=142.1 [M]+.

Workup

  1. temperatureThe resulting mixture was then heated
  2. temperatureunder reflux for 16 h
  3. filtrationfiltered
  4. customevaporated
  5. customchromatographed (SiO2, dichloromethane:methanol=95:5 to 90:10)

Sources & evidence

ORD record
ord-eee3ae66b2de48798d85d450d673db46
Source dataset
uspto-grants-2009_03
Patent number
US07507729B2

Reaction notes

Loading…