Water → 2-(4-Chlorophenyl)-2-[1-(3-chloro-1,2,4-triazol-1-yl)-cyclopropyl]oxirane
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]=1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 40 °C
Procedure
60 ml of absolute dimethyl sulphoxide are added dropwise at 10° C. under a nitrogen atmosphere to a stirred mixture of 2.5 g (83 mmol) of sodium hydride (80 per cent of substance) and 17.6 g (80 mmol) of trimethyl sulphoxonium iodide. Stirring is continued for one hour at 20° C., and a solution of 20 g (71 mmol) of 1-(4-chlorobenzoyl)-1-(3-chloro-1,2,4-triazol-1-yl)-cyclopropane in 30 ml of dimethyl sulphoxide is subsequently added at 10° C. After the reaction mixture has been stirred for 48 hours at 20° C., it is warmed for another hour at 40° C. and then poured into water. The mixture is extracted several times using ethyl acetate, and the combined organic phases are washed with water, dried over sodium sulphate and concentrated by stripping off the solvent under reduced pressure. This procedure gives 21 g (100% of theory) of 2-(4-chlorophenyl)-2-[1-(3-chloro-1,2,4-triazol-1-yl)-cyclopropyl]-oxirane in the form of an oil. 1H-NMR (200 MHz, CDCl3): δ=0.8-1.4 (m, 4H); 2.92 (d, 1H); 3.15 (d, 1H); 7.10 (d, 2 H); 7.38 (d, 2H); 7.75 (s, 1H). ##STR18##
Workup
- stirringAfter the reaction mixture has been stirred for 48 hours at 20° C.
- extractionThe mixture is extracted several times
- washthe combined organic phases are washed with water
- dry with materialdried over sodium sulphate
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-67a00124b04449b1abe2050bff1c5783
- Source dataset
- uspto-grants-1992_03
- Patent number
- US05096913
Reaction notes
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