Ethanol → HCID 19836381, compound

HRID 845524Notes

Reaction equation

HRID 845524 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 over 0.5 g of 10% strength palladium-on-charcoal in a circulatory hydrogenation apparatus under atmospheric pressure at 20°-45° C. for 1 hour, the catalyst is filtered off and the solution is concentrated in vacuo at 40° C. 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 minutes, the solution is concentrated at 50° C. in vacuo after a short time and 500 ml of icewater are added. 56 g (97% of theoretical) 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 in vacuo at 40° C
  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 minutes
  6. concentrationthe solution is concentrated at 50° C. in vacuo after a short time and 500 ml of icewater
  7. additionare added

Sources & evidence

ORD record
ord-e593f56e7a2945a58299822bd98360d7
Source dataset
uspto-grants-1988_07
Patent number
US04758579

Reaction notes

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