Chlorosuccinimide → 3-fluoro-N-hydroxybenzene-1-carbonimidoyl chloride

HRID 332302

Reaction equation

HRID 332302 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)/[CH:5]=[N:6]\[OH:7].[Cl:11]N1C(=O)CCC1=O>CN(C=O)C>[OH:7]/[N:6]=[C:5](\[Cl:11])/[C:4]1[CH:8]=[CH:9][CH:10]=[C:2]([F:1])[CH:3]=1

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 5582750(E)-N-[(3-Fluorophenyl)methylidene]hydroxylamine

Product 1

HCID 142213383-fluoro-N-hydroxybenzene-1-carbonimidoyl chlorideYield 73%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of (E)- and/or (Z)-3-fluoro-benzaldehyde oxime (6.9 g, 50 mmol) in DMF (50 mL) was added N-chlorosuccinimide (6.6 g, 50 mmol) portionwise over 1 h, keeping the temperature below 35° C. The reaction mixture was stirred at room temperature for 1 h. The mixture was then poured onto ice-water, and extracted with ethyl acetate. The combined organic layers were then washed with water and brine, dried over sodium sulfate and evaporated to afford the title compound (6.3 g, 73%) which was obtained as an off white solid. MS m/e (EI): 173.1 [M].

Workup

  1. customthe temperature below 35° C
  2. additionThe mixture was then poured onto ice-water
  3. extractionextracted with ethyl acetate
  4. washThe combined organic layers were then washed with water and brine
  5. dry with materialdried over sodium sulfate
  6. customevaporated

Sources & evidence

ORD record
ord-e8a6a4b7fb144524a46bf8e378ad6ce6
Source dataset
uspto-grants-2014_11
Patent number
US08877783B2

Linked notes

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