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

HRID 2352125Notes

Reaction equation

HRID 2352125 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 drop-wise to a boiling solution of 100 g of potassium carbonate and 110 g of 1,2,4-triazol in 400 ml of acetone, and the mixture is then stirred under reflux for 8 hours. Thereafter, it is evaporated down in vacuo, and the residue is stirred in 500 ml of water. The precipitate which separates out is filtered off under 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. ##STR56##

Workup

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

Sources & evidence

ORD record
ord-6f0cb39b6c9b465ea1a18d8209feabcb
Source dataset
uspto-grants-1989_10
Patent number
US04875928

Reaction notes

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