Sodium Carbonate → (E)-4-chloro-3-trifluoromethyl-cinnamamide oxime

HRID 22367Notes

Reaction equation

HRID 22367 reaction equation
[Cl:1][C:2]1[CH:11]=[CH:10][C:5]([CH:6]=[CH:7][C:8]#[N:9])=[CH:4][C:3]=1[C:12]([F:15])([F:14])[F:13].Cl.[NH2:17][OH:18].C(=O)([O-])[O-].[Na+].[Na+]>O.C(O)C>[Cl:1][C:2]1[CH:11]=[CH:10][C:5](/[CH:6]=[CH:7]/[C:8](=[N:17][OH:18])[NH2:9])=[CH:4][C:3]=1[C:12]([F:13])([F:14])[F:15]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 443297Hydroxyamine hydrochlorideHCID 541762263-[4-Chloro-3-(trifluoromethyl)phenyl]prop-2-enenitrile

Product 1

HCID 86748304(E)-4-chloro-3-trifluoromethyl-cinnamamide oximeYield 40.1%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

12.1 g (0.05 mol) of 4-chloro-3-trifluoromethylcinnamonitrile are added to a solution consisting of 7.2 g (0.10 mol) of hydroxylamine hydrochloride and 7.3 g (0.10 mol) of sodium carbonate in 100 ml of water and 100 ml of ethanol. The mixture is heated at reflux temperature until the reaction is complete (24 hours) and the whole batch is subsequently stirred into 250 ml of water. The solid material which separates off during this process is filtered off with suction, washed with a little water and dried. 5.3 g (39.3% of theory) of (E)-4-chloro-3-trifluoromethylcinnamamide oxime are obtained.

Workup

  1. temperatureThe mixture is heated
  2. temperatureat reflux temperature until the reaction
  3. custom(24 hours)
  4. filtrationis filtered off with suction
  5. washwashed with a little water
  6. customdried

Sources & evidence

ORD record
ord-fb2b92ea32f44d1c8911e32d2d50f6de
Source dataset
uspto-grants-1995_06
Patent number
US05428049

Reaction notes

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