Chlorosuccinimide → HCID 85444714, compound

HRID 1025762Notes

Reaction equation

HRID 1025762 reaction equation
[F:1][C:2]([F:13])([F:12])[C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][CH:11]=1)[CH:6]=[N:7][OH:8].[Cl:14]N1C(=O)CCC1=O>C(Cl)Cl.O>[OH:8][N:7]=[C:6]([Cl:14])[C:5]1[CH:9]=[CH:10][CH:11]=[C:3]([C:2]([F:12])([F:13])[F:1])[CH:4]=1

Participants

5

Reactant 2

HCID 31398ChlorosuccinimideHCID 2777383N-{[3-(Trifluoromethyl)phenyl]methylidene}hydroxylamine

Product 1

HCID 85444714HCID 85444714, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
45 °C

Procedure

To a dried flask containing 3-(trifluoromethyl)benzaldehyde oxime (1.89 g, 10 mol) in methylene chloride (100 mL) was added N-chlorosuccinimide (1.40 g, 10.5 mmol) slowly at 0° C. The reaction mixture was warmed to 45° C. for 2 h, poured over ice, diluted with H2O (20 mL), and extracted with EtOAc (100 mL). The organic phase was washed with H2O (2×25 mL) and saline solution (25 mL), dried over sodium sulfate, concentrated in vacuo to give N-hydroxy-3-(trifluoromethyl)benzenecarboximidoyl chloride (2 g, 90%). LCMS: 224.4 (M+H)+.

Workup

  1. additionpoured over ice
  2. extractionextracted with EtOAc (100 mL)
  3. washThe organic phase was washed with H2O (2×25 mL) and saline solution (25 mL)
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-77be7d9bf97f44f9a16db6c70d157c99
Source dataset
uspto-grants-2014_05
Patent number
US08729063B2

Reaction notes

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