Chlorosuccinimide → 4-fluoro-N-hydroxybenzenecarboximidoyl chloride

HRID 606070Notes

Reaction equation

HRID 606070 reaction equation
[Cl:1]N1C(=O)CCC1=O.[F:9][C:10]1[CH:18]=[CH:17][C:13]([CH:14]=[N:15][OH:16])=[CH:12][CH:11]=1>CN(C=O)C>[F:9][C:10]1[CH:18]=[CH:17][C:13]([C:14]([Cl:1])=[N:15][OH:16])=[CH:12][CH:11]=1

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 68017N-[(4-fluorophenyl)methylidene]hydroxylamine

Product 1

HCID 27563164-fluoro-N-hydroxybenzenecarboximidoyl chlorideYield 68.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
40 °C

Procedure

N-Chlorosuccinimide (85.5 g, 438 mmol) was added to a solution of 4-fluorobenzaldehyde oxime (61.0 g, 438 mmol) in DMF (100 mL) at room temperature; an exotherm occurred. After the addition, the solution was heated at 40° C. for 30 minutes under nitrogen. The solution was poured onto ice and extracted with chloroform. The combined extracts were washed with brine, dried over magnesium sulfate, filtered, and concentrated under reduced pressure, and further dried under high vacuum for 16 hours to provide 52.23 g of 4-fluoro-N-hydroxybenzenecarboximidoyl chloride as an amber oil.

Workup

  1. additionAfter the addition
  2. additionThe solution was poured onto ice
  3. extractionextracted with chloroform
  4. washThe combined extracts were washed with brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customfurther dried under high vacuum for 16 hours

Sources & evidence

ORD record
ord-23b16744807545f7ba07c21803ebcf7d
Source dataset
uspto-grants-2011_03
Patent number
US07915281B2

Reaction notes

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