Chlorosuccinimide → HCID 86622732, compound

HRID 2410345Notes

Reaction equation

HRID 2410345 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]([O:11][CH2:12][CH:13]([CH3:15])[CH3:14])[C:3]=1[CH:4]=[N:5][OH:6].[Cl:16]N1C(=O)CCC1=O>CN(C)C=O.C(OC(=O)C)C.CCCCCC>[F:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]([O:11][CH2:12][CH:13]([CH3:15])[CH3:14])[C:3]=1[C:4]([Cl:16])=[N:5][OH:6]

Participants

6

Reactant 2

HCID 31398ChlorosuccinimideHCID 86622731HCID 86622731, compound

Product 1

HCID 86622732HCID 86622732, compoundYield 90.1%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 2-fluoro-6-isobutoxybenzaldehyde oxime (0.99 g, 6.1 mmol, EXAMPLE 16, Step 3) in N,N-dimethylformamide (20 mL) was added N-chlorosuccinimide (0.63 g, 4.7 mmol) at 0° C. The mixture was heated at 50° C. for 1 h and cooled to room temperature. The mixture was diluted with ethylacetate (30 mL) and hexane (30 mL). The organic layer was washed with water (30 mL×2), dried over magnesium sulfate and concentrated in vacuo to give an oil. The residual oil was purified by silica gel column chromatography (hexane/ethyl acetate 9:1 to 4:1) to give 1.04 g (90%) of the title compound as a pale yellow oil.

Workup

  1. temperaturecooled to room temperature
  2. washThe organic layer was washed with water (30 mL×2)
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. customto give an oil
  6. customThe residual oil was purified by silica gel column chromatography (hexane/ethyl acetate 9:1 to 4:1)

Sources & evidence

ORD record
ord-48abb524340e4291a141283a6664c236
Source dataset
uspto-grants-2014_08
Patent number
US08816090B2

Reaction notes

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