Acetic Acid → 2-(1-Chloro-cyclopropyl)-1-(2-chlorophenyl)-3-(5-methylsulphonyl-1,2,4-triazol-1-yl)-propan-2-ol

HRID 481471Notes

Reaction equation

HRID 481471 reaction equation
[Cl:1][C:2]1([C:5]([OH:22])([CH2:14][N:15]2[C:19]([S:20][CH3:21])=[N:18][CH:17]=[N:16]2)[CH2:6][C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[Cl:13])[CH2:4][CH2:3]1.OO.[OH-:25].[Na+].C(O)(=[O:29])C>>[Cl:1][C:2]1([C:5]([OH:22])([CH2:14][N:15]2[C:19]([S:20]([CH3:21])(=[O:29])=[O:25])=[N:18][CH:17]=[N:16]2)[CH2:6][C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[Cl:13])[CH2:4][CH2:3]1

Participants

5

Reactant 4

HCID 176Acetic AcidHCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 185067551H-1,2,4-Triazole-1-ethanol, alpha-(1-chlorocyclopropyl)-alpha-((2-chlorophenyl)methyl)-5-(methylthio)-

Product 1

HCID 542027302-(1-Chloro-cyclopropyl)-1-(2-chlorophenyl)-3-(5-methylsulphonyl-1,2,4-triazol-1-yl)-propan-2-olYield 51%

Procedure

A solution of 3.57 g (10 mmol) of 2-(1-chlorocyclopropyl)-1-(2-chlorophenyl)-3-(5-methylthio-1,2,4-triazol-1-yl)-propan-2-ol in 40 ml of glacial acetic acid is treated dropwise at 90° C. with stirring with 4 ml of an aqueous hydrogen peroxide solution (35% strength). After the addition has ended, stirring of the reaction mixture is continued at 90° C. for 30 minutes, and the mixture is then cooled to room temperature, treated with ice and rendered alkaline by adding aqueous sodium hydroxide solution. The mixture is extracted repeatedly using ethyl acetate, and the combined organic phases are dried over sodium sulphate and concentrated under reduced pressure. The slowly crystallizing product which remains is filtered off with suction. In this manner, 2.0 g (51% of theory) of 2-(1-chloro-cyclopropyl)-1-(2-chlorophenyl)-3-(5-methylsulphonyl-1,2,4-triazol-1-yl)-propan-2-ol) are obtained in the form of a solid which melts at 125°-128° C.

Workup

  1. additionAfter the addition
  2. additiontreated with ice
  3. extractionThe mixture is extracted repeatedly using ethyl acetate
  4. dry with materialthe combined organic phases are dried over sodium sulphate
  5. concentrationconcentrated under reduced pressure
  6. filtrationThe slowly crystallizing product which remains is filtered off with suction

Sources & evidence

ORD record
ord-49c36a83dd6c4437aa735113dc9073c0
Source dataset
uspto-grants-1998_08
Patent number
US05789430

Reaction notes

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