Chlorosuccinimide → 4-Chloro-N-hydroxybenzimidoyl chloride

HRID 1911654Notes

Reaction equation

HRID 1911654 reaction equation
FC1C=CC(C=O)=CC=1.[Cl:10][C:11]1[CH:19]=[CH:18][C:14](/[CH:15]=[N:16]\[OH:17])=[CH:13][CH:12]=1.[Cl:20]N1C(=O)CCC1=O>CN(C=O)C>[OH:17]/[N:16]=[C:15](\[Cl:20])/[C:14]1[CH:18]=[CH:19][C:11]([Cl:10])=[CH:12][CH:13]=1

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 87630081(NZ)-N-[(4-chlorophenyl)methylidene]hydroxylamine;4-fluorobenzaldehyde

Product 1

HCID 72718654-Chloro-N-hydroxybenzimidoyl chlorideYield 86.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of (E)- and/or (Z)-4-chloro-benzaldehyde oxime 4-fluorobenzaldehyde (27.0 g, 173 mmol) in DMF (173 mL) was added N-chlorosuccinimide (22.8 g, 173 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 (28.4 g, 86%) which was obtained as a light yellow solid. MS: m/e=189.1 [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-89e21046a7b846fd8e5313bbbe87caa2
Source dataset
uspto-grants-2013_12
Patent number
US08604062B2

Reaction notes

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