Water → HCID 19876896, compound

HRID 1948833Notes

Reaction equation

HRID 1948833 reaction equation
[CH:1](=[N:8]/[OH:9])\[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl:10]N1C(=O)CCC1=O.O>C(Cl)Cl>[Cl:10][C:2]1([CH:7]=[CH:6][CH:5]=[CH:4][CH2:3]1)/[CH:1]=[N:8]/[OH:9]

Participants

5

Reactant 3

HCID 962WaterHCID 31398ChlorosuccinimideHCID 5324611Benzaldehyde Oxime

Product 1

HCID 19876896HCID 19876896, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

After dissolving (E)-benzaldehyde oxime (3.0 g, 25 mmol) in CH2Cl2 (30 ml), N-chlorosuccinimide (3.4 g, 25 mmol) was slowly added at 0° C. After stirring reaction solution for 2 hours, the reaction was completed by adding water (20 ml), and the reaction solution was extracted with dichloromethane. A pure compound of (E)-1-chloro-benzaldehyde oxime (3.30 g, 85%) was obtained by separating the residue with silica gel column chromatography. After dissolving the (E)- and (Z)-oxime mixtures (1.5 g, 9.64 mmol) in CH2Cl2 (30 ml), benzoylchloride (1.45 ml, 12.53 mmol) was slowly added at 0° C. under the presence of triethylamine (1.75 ml, 12.53 mmol). After stirring reaction solution for 1 hour, the reaction was quenched by 1 N hydrochloric acid, and the reaction solution was extracted with dichloromethane. A pure compound of (E)-1-chloro-benzaldehyde O-benzoyloxime (15) (1.9 g, 76%) was obtained by separating the residue with silica gel column chromatography.

Workup

  1. additionwas slowly added at 0° C
  2. customreaction solution for 2 hours
  3. extractionthe reaction solution was extracted with dichloromethane

Sources & evidence

ORD record
ord-7d1ea2502a1842cd86a9bd2c76001c83
Source dataset
uspto-grants-2013_03
Patent number
US08399662B2

Reaction notes

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