Potassium Carbonate → 1-(4-Chlorobenzoyl)-1-(3-chloro-1,2,4-triazol-1-yl)-cyclopropane

HRID 893627Notes

Reaction equation

HRID 893627 reaction equation
C(=O)([O-])[O-].[K+].[K+].[Cl:7][C:8]1[N:12]=[CH:11][NH:10][N:9]=1.Br[CH:14]([CH2:24][CH2:25]Cl)[C:15]([C:17]1[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=1)=[O:16]>CC(C)=O>[Cl:23][C:20]1[CH:21]=[CH:22][C:17]([C:15]([C:14]2([N:10]3[CH:11]=[N:12][C:8]([Cl:7])=[N:9]3)[CH2:25][CH2:24]2)=[O:16])=[CH:18][CH:19]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 1071672-Bromo-4-chloro-1-(4-chlorophenyl)butan-1-oneHCID 178478410HCID 178478410, compound

Product 1

HCID 146972271-(4-Chlorobenzoyl)-1-(3-chloro-1,2,4-triazol-1-yl)-cyclopropaneYield 90%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

34 g (246 mmol) of potassium carbonate and 35 g (338 mmol) of 3-chloro-1,2,4-triazole are initially introduced into 130 ml of acetone under reflux and 50 g (169 mol) of 2-bromo-4-chloro-1-(4-chlorophenyl)-butan-1-one in 60 ml of acetone are added dropwise. The mixture is boiled under reflux for 8 hours, the solution is filtered off with suction from the residue and the solvent is stripped off in vacuo. The residue is taken up in ethyl acetate, washed with water and dried over sodium sulphate, and the solvent is evaporated. Chromatography on silica gel (eluent: dichloromethane) gives 42.9 g of the title compound (90% of theory) of m.p. 85° C.

Workup

  1. temperatureunder reflux
  2. temperatureunder reflux for 8 hours
  3. filtrationthe solution is filtered off with suction from the residue
  4. washwashed with water
  5. dry with materialdried over sodium sulphate
  6. customthe solvent is evaporated

Sources & evidence

ORD record
ord-ca0768b7f1a34bbbb62ba7fdc517292f
Source dataset
uspto-grants-1992_06
Patent number
US05126359

Reaction notes

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