Ethanol → [(E)-3-[4-chloro-3-(trifluoromethyl)phenyl]prop-2-enoyl]-oxidoazanium

HRID 1491971Notes

Reaction equation

HRID 1491971 reaction equation
[Cl:1][C:2]1[CH:11]=[CH:10][C:5]([CH:6]=[CH:7]C#N)=[CH:4][C:3]=1[C:12]([F:15])([F:14])[F:13].Cl.[NH2:17][OH:18].[C:19](=[O:22])([O-])[O-].[Na+].[Na+].C(O)C>O>[Cl:1][C:2]1[CH:11]=[CH:10][C:5](/[CH:6]=[CH:7]/[C:19]([NH2:17]=[O:18])=[O:22])=[CH:4][C:3]=1[C:12]([F:15])([F:14])[F:13]

Participants

6

Reactant 4

HCID 702EthanolHCID 10340Sodium CarbonateHCID 443297Hydroxyamine hydrochlorideHCID 541762263-[4-Chloro-3-(trifluoromethyl)phenyl]prop-2-enenitrile

Product 1

HCID 23364570[(E)-3-[4-chloro-3-(trifluoromethyl)phenyl]prop-2-enoyl]-oxidoazaniumYield 39.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

12.1 g (0.05 mol) of 4-chloro-3-trifluoromethyl-cinnamonitrile are added to a solution of 7.2 g (0.10 mol) of hydroxylamine hydrochloride, 7.3 g (0.10 mol) of sodium carbonate in 100 ml of water, and 100 ml of ethanol. The mixture is refluxed until the reaction is complete (24 hours) and the entire batch is subsequently stirred into 250 ml of water. The solid which separates out 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-trifluoromethyl-cinnamamide oxide are obtained.

Workup

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

Sources & evidence

ORD record
ord-068deb44a5de4ac58aed5685f015a7f9
Source dataset
uspto-grants-1994_12
Patent number
US05371231

Reaction notes

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