Chloroform → alpha-Chloro-3-nitrobenzaldoxime

HRID 328653Notes

Reaction equation

HRID 328653 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][CH:12]=1)[CH:7]=[N:8][OH:9])([O-:3])=[O:2].C(Cl)(Cl)[Cl:14]>>[Cl:14][C:7](=[N:8][OH:9])[C:6]1[CH:10]=[CH:11][CH:12]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=1

Participants

3

Reactant 2

HCID 6212ChloroformHCID 2191323-Nitrobenzaldoxime

Product 1

HCID 2756318alpha-Chloro-3-nitrobenzaldoximeYield 93.7%

Procedure

32.9 g (0.2 mol) of 3-nitrobenzaldoxime was suspended in 150 g of chloroform and chlorine gas was bubbled into the suspension while maintaining the reaction mixture at a temperature of from 5° to 10° C. 3-Nitrobenzaldoxime went into solution showing a green color upon reaction with chlorine to give a reaction mixture having a deep green color. The reaction mixture turned a pale yellowish-brown upon standing; chloroform was then removed from the reaction mixture under reduced pressure to give 37.6 g of pale yellow crystals having a melting point of 98°-101° C. Yield, 94%.

Workup

  1. customchlorine gas was bubbled into the suspension
  2. temperaturewhile maintaining the reaction mixture at a temperature of from 5° to 10° C
  3. customupon reaction with chlorine
  4. customto give a reaction mixture
  5. customchloroform was then removed from the reaction mixture under reduced pressure

Sources & evidence

ORD record
ord-dc39e48f4844465387e4cd39efcfb0d4
Source dataset
uspto-grants-1977_04
Patent number
US04018645

Reaction notes

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