Chlorine → 4-chloro-N-hydroxybenzene-1-carbonimidoyl chloride

HRID 1576973Notes

Reaction equation

HRID 1576973 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]Cl>C(Cl)(Cl)Cl>[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([Cl:11])=[N:7][OH:8])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 24526ChlorineHCID 2191584-Chloro-benzaldehyde oxime

Product 1

HCID 27555434-chloro-N-hydroxybenzene-1-carbonimidoyl chloride

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A solution of 16.75 g of 4-chlorobenzaldoxime in 155 ml of chloroform was cooled to 5°. Chlorine gas was passed slowly through the solution until no more was absorbed; a blue-green color developed and the temperature slowly increased to 20°. The mixture was stirred for 1 hour at 5°, then heated under reflux for half an hour. The mixture was cooled to room temperature, then the solvent was evaporated under reduced pressure to give a white solid. The solid was collected and dried in a vacuum desiccator in a refrigerator at 5° to give 20.4 g of 4-chlorobenzohydroximoyl chloride, m.p. 81°-85°.

Workup

  1. customno more was absorbed
  2. temperaturethe temperature slowly increased to 20°
  3. temperatureheated
  4. temperatureunder reflux for half an hour
  5. customthe solvent was evaporated under reduced pressure
  6. customto give a white solid
  7. customThe solid was collected
  8. customdried in a vacuum desiccator in a refrigerator at 5°

Sources & evidence

ORD record
ord-1210d96c0fd3483ea17a310240f0c9f2
Source dataset
uspto-grants-1976_09
Patent number
US03983246

Reaction notes

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