Hydrochloric Acid → (1Z)-1-(2,4-Dichlorophenyl)-2-(1H-imidazol-1-yl)ethanone oxime

HRID 465136Notes

Reaction equation

HRID 465136 reaction equation
[Cl:1][C:2]1[CH:15]=[C:14]([Cl:16])[CH:13]=[CH:12][C:3]=1[C:4](=O)[CH2:5][N:6]1[CH:10]=[CH:9][N:8]=[CH:7]1.[Cl-].[OH:18][NH3+:19].[OH-].[K+].Cl>CO>[Cl:1][C:2]1[CH:15]=[C:14]([Cl:16])[CH:13]=[CH:12][C:3]=1/[C:4](=[N:19]/[OH:18])/[CH2:5][N:6]1[CH:10]=[CH:9][N:8]=[CH:7]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 21645Hydroxylamine HClHCID 322321-(2,4-Dichlorophenyl)-2-(1H-imidazol-1-yl)ethan-1-one

Product 1

HCID 5480616(1Z)-1-(2,4-Dichlorophenyl)-2-(1H-imidazol-1-yl)ethanone oxime

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1240 g (4.9 moles) of the thus prepared 2,4-dichlorophenacyl-1H-imidazol is dissolved in 6.2 l methanol. 506.6 g (7.3 moles) hydroxylammonium chloride and 818.2 g KOH (14.6 moles) are added to this solution, which then is heated for one hour under reflux while stirring. After cooling the reaction mixture is poured into 5330 ml aqueous HCl having a concentration of 5% by weight, whereby the oxime product is precipitated. About one hour later the solig product is filtered off and well washed with water. Then after well drying the thus obtained raw product is recrystallized from ethylene glycol monomethyl ether. The pure oxime product, i.e. the (Z)-1-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl)-ethanone oxime thus is obtained in the form of colourless crystals having a melting point of 227°-229° C. The yield is 89%. The purity and the identity of the obtained product were confirmed by chemical analysis, TLC, NMR and IR absorption spectra.

Workup

  1. temperaturethen is heated for one hour
  2. temperatureunder reflux
  3. temperatureAfter cooling the reaction mixture
  4. customis precipitated
  5. filtrationAbout one hour later the solig product is filtered off
  6. washwell washed with water
  7. customThen after well drying the
  8. customthus obtained raw product
  9. customis recrystallized from ethylene glycol monomethyl ether

Sources & evidence

ORD record
ord-1251f58c3b1f45398c49b186500ba433
Source dataset
uspto-grants-1985_10
Patent number
US04550175

Reaction notes

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