Ethanol → HCID 19836381, compound

HRID 1584000Notes

Reaction equation

HRID 1584000 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([O:10][C:11]([F:16])([F:15])[CH:12]([F:14])[F:13])=[CH:6][CH:5]=1)([O-])=O.[CH2:17]([OH:19])[CH3:18]>[Pd]>[F:15][C:11]([F:16])([O:10][C:7]1[CH:8]=[CH:9][C:4]([NH:1][C:17](=[O:19])[CH3:18])=[CH:5][CH:6]=1)[CH:12]([F:14])[F:13]

Participants

4

Reactant 2

HCID 702EthanolHCID 1198934-(1,1,2,2-Tetrafluoroethoxy)nitrobenzene

Product 1

HCID 19836381HCID 19836381, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

55 g of 1-nitro-4-(1,1,2,2-tetrafluoroethoxy)benzene are hydrogenated in 300 ml of ethanol on 0.5 g of 10% strength palladium-on-charcoal in a circulatory hydrogenation apparatus under atmospheric pressure at 20°-45° C. for 1 h, the catalyst is filtered off and the solution is concentrated at 40° C. in vacuo. The 4-(1,1,2,2-tetrafluoroethoxy)aniline is diluted with 100 ml of glacial acetic acid, 23 ml of acetic anhydride are added dropwise at room temperature, 2 ml of water are added after 30 min., the solution is concentrated in vacuo at 50° C. after a short time and 500 ml of ice-water are added. 56 g (97%) of N-[4-(1,1,2,2-tetrafluoroethoxy)phenyl]-acetamide of m.p. 121°-122° C. are obtained.

Workup

  1. filtrationthe catalyst is filtered off
  2. concentrationthe solution is concentrated at 40° C. in vacuo
  3. additionThe 4-(1,1,2,2-tetrafluoroethoxy)aniline is diluted with 100 ml of glacial acetic acid, 23 ml of acetic anhydride
  4. additionare added dropwise at room temperature
  5. addition2 ml of water are added after 30 min.
  6. concentrationthe solution is concentrated in vacuo at 50° C. after a short time and 500 ml of ice-water
  7. additionare added

Sources & evidence

ORD record
ord-b5849e066c4841718d338dd919e3f55c
Source dataset
uspto-grants-1985_11
Patent number
US04555518

Reaction notes

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