Hydrochloric Acid → N-hydroxybenzenecarboximidoyl chloride

HRID 917983Notes

Reaction equation

HRID 917983 reaction equation
[CH:1](=[N:8][OH:9])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[ClH:10]>>[Cl:10][C:1](=[N:8][OH:9])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 12143(Z)-Benzaldehyde oxime

Product 1

HCID 2756315N-hydroxybenzenecarboximidoyl chloride

Procedure

60.5 g (0.5 mol) of benzaldoxime was suspended in 390 ml of 8N hydrochloric acid and chlorine gas was bubbled into the suspension while stirring and maintaining the reaction temperature at from 5° to 15°C. The oxime immediately showed a green color upon reaction with chlorine and, after allowing the reaction mixture to stand, pale yellow crystals of α-chlorobenzaldoxime precipitated. Filtration of the reaction mixture yielded 66 g of crystals having a melting point of 45°-47°C. Yield, about 84%.

Workup

  1. customchlorine gas was bubbled into the suspension
  2. temperaturemaintaining the reaction temperature at from 5° to 15°C
  3. customupon reaction with chlorine
  4. custompale yellow crystals of α-chlorobenzaldoxime precipitated
  5. filtrationFiltration of the reaction mixture

Sources & evidence

ORD record
ord-ef0f52cfbcd343a1bb1d4839a56b66da
Source dataset
uspto-grants-1976_07
Patent number
US03968240

Reaction notes

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