Water → 1-(4-Chlorobenzyl)-1-(1, 2, 4-triazol-1-yl)-cyclopropane

HRID 1761893Notes

Reaction equation

HRID 1761893 reaction equation
[N:1]1([C:6]2([C:9]([C:11]3[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][CH:12]=3)=O)[CH2:8][CH2:7]2)[CH:5]=[N:4][CH:3]=[N:2]1.O.NN.[OH-].[K+].O>C(O)COCCO>[Cl:17][C:14]1[CH:13]=[CH:12][C:11]([CH2:9][C:6]2([N:1]3[CH:5]=[N:4][CH:3]=[N:2]3)[CH2:7][CH2:8]2)=[CH:16][CH:15]=1

Participants

6

Reactant 4

HCID 962WaterHCID 14797Potassium HydroxideHCID 24654Hydrazine hydrate (1:1)HCID 136504511-(4-Chlorobenzoyl)-1-(1,2,4-triazol-1-yl)cyclopropane

Product 1

HCID 141259771-(4-Chlorobenzyl)-1-(1, 2, 4-triazol-1-yl)-cyclopropaneYield 57.8%

Reagents, catalysts & solvents 1

HCID 8117Diethylene GlycolSolvent

Procedure

A suspension of 24.8 g (0.1 mol) of 4-chlorophenyl 1-(1, 2, 4-triazol-1-yl)-cyclopropyl ketone with 19.8 g of 80% strength hydrazine hydrate in 40 ml of diethylene glycol was refluxed for 1 hour and cooled, and 14.3 g of powdered potassium hydroxide were added to the clear yellow solution. The mixture was refluxed, and the resultant water of reaction was then distilled off until the diethylene glycol again refluxed. After 1 hour, the mixture was poured into water and extracted with dichloromethane; after drying, the solvent was removed in vacuo and the residue remaining was distilled in a high vacuum. 13.5 g (57%) of the title compound were obtained as a yellowish oil, of boiling point 154°-156° C./0.05, which crystallized with melting point 67°-8° C.

Workup

  1. temperaturewas refluxed for 1 hour
  2. temperaturecooled
  3. temperatureThe mixture was refluxed
  4. distillationwas then distilled off until the diethylene glycol
  5. temperatureagain refluxed
  6. additionthe mixture was poured into water
  7. extractionextracted with dichloromethane
  8. customafter drying
  9. customthe solvent was removed in vacuo
  10. distillationthe residue remaining was distilled in a high vacuum

Sources & evidence

ORD record
ord-f8c97b43eb6946bb926ecdf9dfbb75ae
Source dataset
uspto-grants-1989_05
Patent number
US04829075

Reaction notes

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