Chlorosuccinimide → 4-Chloro-N-hydroxybenzimidoyl chloride

HRID 1911649Notes

Reaction equation

HRID 1911649 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:5](/[CH:6]=[N:7]\[OH:8])=[CH:4][CH:3]=1.[Cl:11]N1C(=O)CCC1=O>CN(C=O)C>[OH:8]/[N:7]=[C:6](\[Cl:11])/[C:5]1[CH:9]=[CH:10][C:2]([Cl:1])=[CH:3][CH:4]=1

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 5354056anti-p-Chlorobenzaldoxime

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 (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-95d443c3c76c4799a3bbce96a955578f
Source dataset
uspto-grants-2013_12
Patent number
US08604062B2

Reaction notes

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