Water → 2-(4-Chlorophenyl)-2-[1-(3-chloro-1,2,4-triazol-1-yl)-cyclopropyl]oxirane

HRID 893628Notes

Reaction equation

[H-].[Na+].[I-].[CH3:4][S+](C)(C)=O.[Cl:9][C:10]1[CH:26]=[CH:25][C:13]([C:14]([C:16]2([N:19]3[CH:23]=[N:22][C:21]([Cl:24])=[N:20]3)[CH2:18][CH2:17]2)=[O:15])=[CH:12][CH:11]=1.O>CS(C)=O>[Cl:9][C:10]1[CH:11]=[CH:12][C:13]([C:14]2([C:16]3([N:19]4[CH:23]=[N:22][C:21]([Cl:24])=[N:20]4)[CH2:17][CH2:18]3)[CH2:4][O:15]2)=[CH:25][CH:26]=1

Participants

Conditions

Temperature: 20 °C

Procedure

2.5 g (83 mmol) of sodium hydride (80% strength) and 17.6 g (80 mmol) of trimethylsulphoxonium iodide are initially introduced under a nitrogen atmosphere and 60 ml of absolute dimethyl sulphoxide are added dropwise at 10° C. The mixture is stirred for 1 hour at 20° C. and then 20 g (71 mmol) of 1-(4-chlorobenzoyl)-1-(3-chloro-1,2,4-triazol-1-yl)-cyclopropane dissolved in 30 ml of absolute dimethyl sulphoxide are added at 10° C. After 48 hours at 20° C., the mixture is warmed to 40° C. for 1 hour and the reaction solution is then poured into water. The mixture is extracted with ethyl acetate, the combined organic phases are washed with water and dried over sodium sulphate, and the solvent is evaporated in vacuo. 21 g of the title compound (100 % of theory) remain in the form of an oil.

Workup

additionare added at 10° C
waitAfter 48 hours at 20° C.
temperaturethe mixture is warmed to 40° C. for 1 hour
extractionThe mixture is extracted with ethyl acetate
washthe combined organic phases are washed with water
dry with materialdried over sodium sulphate
customthe solvent is evaporated in vacuo

Sources & evidence

ORD record: ord-105799d7c3274e6784070d6d8dd6a5b2
Source dataset: uspto-grants-1992_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05126359

Reaction notes

Loading…