Trifluoroacetic anhydride → HCID 13178614, compound

HRID 1074909Notes

Reaction equation

HRID 1074909 reaction equation
FC(F)(F)C([O:5][C:6](=[O:11])[C:7]([F:10])([F:9])[F:8])=O.[F:14][CH2:15][C:16]([NH:18]O)=[O:17]>>[F:14][CH2:15][C:16]([NH:18][O:5][C:6](=[O:11])[C:7]([F:8])([F:9])[F:10])=[O:17]

Participants

3

Reactant 2

HCID 9845Trifluoroacetic anhydrideHCID 130033112-Fluoro-N-hydroxyacetamide

Product 1

HCID 13178614HCID 13178614, compoundYield 93%

Procedure

Trifluoroacetic anhydride, 71 ml (0.5 mol), was added dropwise to a 37.22 g (0.4 mol) sample of powdered 2-fluoroacetohydroxamic acid. The reaction mixture became liquid and warmed spontaneously to 60°. After cooling, the reaction mixture was evaporated to dryness under reduced pressure to give 70.3 g (93%) of N-(fluoroacetyl)-O-(trifluoroacetyl)hydroxylamine as a colorless, crystalline residue: mp 56°-59°; 1H NMR (CDCl3) δ 5.05 ppm (d, J=47 Hz, 2H) and 9.8 ppm (NH); 19F NMR (CDCl3) δ -233.8 ppm (t, J=47 Hz, 1F) and 73.8 ppm (s, 3F).

Workup

  1. temperaturewarmed spontaneously to 60°
  2. temperatureAfter cooling
  3. customthe reaction mixture was evaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-c4484f249b38444ba033f6ea5e7f93cf
Source dataset
uspto-grants-1983_07
Patent number
US04394386

Reaction notes

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