1H-1,2,4-Triazole → 1-(4-Chlorobenzoyl)-1-(1,2,4-triazol-1-yl)cyclopropane

HRID 1165487Notes

Reaction equation

HRID 1165487 reaction equation
Br[CH:2]([C:6]([C:8]1[CH:13]=[CH:12][C:11]([Cl:14])=[CH:10][CH:9]=1)=[O:7])[CH2:3][CH2:4]Cl.C(=O)([O-])[O-].[K+].[K+].[NH:21]1[CH:25]=[N:24][CH:23]=[N:22]1>CC(C)=O>[Cl:14][C:11]1[CH:12]=[CH:13][C:8]([C:6]([C:2]2([N:21]3[CH:25]=[N:24][CH:23]=[N:22]3)[CH2:4][CH2:3]2)=[O:7])=[CH:9][CH:10]=1

Participants

5

Reactant 3

HCID 92571H-1,2,4-TriazoleHCID 11430Potassium CarbonateHCID 1071672-Bromo-4-chloro-1-(4-chlorophenyl)butan-1-one

Product 1

HCID 136504511-(4-Chlorobenzoyl)-1-(1,2,4-triazol-1-yl)cyclopropaneYield 82.9%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

A solution of 150 g of 4-chlorophenyl 1-bromo-3-chloropropyl ketone in 200 ml of acetone is added dropwise to a boiling solution of 100 g of potassium carbonate and 110 g of 1,2,4-triazole in 400 ml of acetone, and the mixture is then stirred under reflux for 8 hours. It is then evaporated in vacuo, and the residue is stirred in 500 ml of water. The precipitate which separates out is filtered off with suction, washed several times with water and dried. 104 g (82% of theory) of 1-(4-chlorobenzoyl)-1-(1,2,4-triazol-1-yl)cyclopropane, of melting point 78° C., are obtained.

Workup

  1. temperatureunder reflux for 8 hours
  2. customIt is then evaporated in vacuo
  3. stirringthe residue is stirred in 500 ml of water
  4. filtrationThe precipitate which separates out is filtered off with suction
  5. washwashed several times with water
  6. customdried

Sources & evidence

ORD record
ord-f2ee2851d07840e0abd590617f68247b
Source dataset
uspto-grants-1990_03
Patent number
US04910213

Reaction notes

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