Sodium Carbonate → HCID 86653073, compound

HRID 339117Notes

Reaction equation

HRID 339117 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6](/[CH:9]=[CH:10]/[C:11]([NH:13][CH:14]([C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([C:25]([F:28])([F:27])[F:26])[CH:20]=2)[C:15]([F:18])([F:17])[F:16])=[O:12])=[CH:5][C:4]=1[C:29]([F:32])([F:31])[F:30])#[N:2].[Cl-].[OH:34][NH3+:35].C(=O)([O-])[O-].[Na+].[Na+]>C(O)C.O>[OH:34][N:35]=[C:1]([C:3]1[CH:8]=[CH:7][C:6](/[CH:9]=[CH:10]/[C:11]([NH:13][CH:14]([C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([C:25]([F:26])([F:27])[F:28])[CH:20]=2)[C:15]([F:16])([F:17])[F:18])=[O:12])=[CH:5][C:4]=1[C:29]([F:30])([F:32])[F:31])[NH2:2]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 21645Hydroxylamine HClHCID 86653074HCID 86653074, compound

Product 1

HCID 86653073HCID 86653073, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

1.17 g (2.51 mmol) of (2E)-3-[4-cyano-3-(trifluoromethyl)phenyl]-N-{2,2,2-trifluoro-1-[3-(trifluoromethyl)phenyl]ethyl}acrylamide from Example Ia-46 were initially charged in a mixture of 11.7 ml of ethanol and 2.9 ml of water and admixed with 209.6 mg (3.01 mmol) of hydroxylammonium chloride and 399.5 mg (3.77 mmol) of sodium carbonate. The reaction mixture was heated under reflux for 18 hours and then admixed with water. After extracting repeatedly with ethyl acetate, the combined organic phases were dried over magnesium sulphate, the solvent was distilled off under reduced pressure and the residue was chromatographed using silica gel with cyclohexane/ethyl acetate as the eluent (gradient from 0% ethyl acetate to 100% ethyl acetate).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureunder reflux for 18 hours
  3. extractionAfter extracting repeatedly with ethyl acetate
  4. dry with materialthe combined organic phases were dried over magnesium sulphate
  5. distillationthe solvent was distilled off under reduced pressure
  6. customthe residue was chromatographed

Sources & evidence

ORD record
ord-2aac72c217f74523ad2915d3f32a8ba6
Source dataset
uspto-grants-2014_11
Patent number
US08889878B2

Reaction notes

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