Chlorosuccinimide → HCID 86229620, compound

HRID 1010701Notes

Reaction equation

HRID 1010701 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][C:8]([C:11]([F:14])([F:13])[F:12])=[CH:7][C:3]=1[CH:4]=[N:5][OH:6].[Cl:15]N1C(=O)CCC1=O>CN(C)C=O.C(OCC)(=O)C>[F:1][C:2]1[CH:10]=[CH:9][C:8]([C:11]([F:12])([F:13])[F:14])=[CH:7][C:3]=1[C:4]([Cl:15])=[N:5][OH:6]

Participants

5

Reactant 2

HCID 31398ChlorosuccinimideHCID 73014307HCID 73014307, compound

Product 1

HCID 86229620HCID 86229620, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 643 mg (3.10 mmol) of 2-fluoro-5-trifluoromethylbenzaldehyde oxime in 5 mL of dimethyl formamide (DMF) was added 456 mg (3.41 mmol) of N-chlorosuccinimide (see K.-C. Liu, B. R. Shelton, and R. K. Howe, J. Org. Chem. 1980, 45, 3916). The reaction mixture was stirred at room temperature overnight, and then diluted with ethyl acetate. The ethyl acetate solution was washed with saturated sodium chloride and dried over magnesium sulfate. The drying agent was filtered off, and solvent was removed by rotoevaporation to give 675 mg (2.79 mmol) of pure white crystalline 2-fluoro-5-trifluoromethyl-N-hydroxybenzene-carboximidoyl chloride.

Workup

  1. washThe ethyl acetate solution was washed with saturated sodium chloride
  2. dry with materialdried over magnesium sulfate
  3. filtrationThe drying agent was filtered off
  4. customsolvent was removed by rotoevaporation

Sources & evidence

ORD record
ord-859d72e488de4a9ea7f515a224fc3315
Source dataset
uspto-grants-2011_07
Patent number
US07977341B2

Reaction notes

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