Water → 5,5-dimethyl-3-(3-ethoxy-1-methyl-5-trifluoromethyl-1H-pyrazol-4-ylmethylthio)-2-isoxazoline

HRID 1172071Notes

Reaction equation

C(=O)([O-])[O-].[K+].[K+].[CH2:7](I)[CH3:8].[CH3:10][C:11]1([CH3:29])[O:15][N:14]=[C:13]([S:16][CH2:17][C:18]2[C:19]([OH:28])=[N:20][N:21]([CH3:27])[C:22]=2[C:23]([F:26])([F:25])[F:24])[CH2:12]1.O>CN(C)C=O>[CH3:10][C:11]1([CH3:29])[O:15][N:14]=[C:13]([S:16][CH2:17][C:18]2[C:19]([O:28][CH2:7][CH3:8])=[N:20][N:21]([CH3:27])[C:22]=2[C:23]([F:26])([F:25])[F:24])[CH2:12]1

Participants

Conditions

Temperature: 50 °C

Procedure

0.20 g (1.3 mmoles) of anhydrous potassium carbonate and 0.20 g (1.5 mmoles) of ethyl iodide were added to a solution of 0.30 g (1.0 mmoles) of 5,5-dimethyl-3-(3-hydroxy-1-methyl-5-trifluoromethyl-1H-pyrazol-4-ylmethylthio)-2-isoxazoline dissolved in 10 ml of N,N-dimethylformamide. The mixture was stirred at 50° C. for 3 hours to give rise to a reaction. After the completion of the reaction, the reaction mixture was poured into water, followed by extraction with ethyl acetate. The resulting-organic layer was washed with an aqueous sodium chloride solution and then dried over anhydrous magnesium sulfate. The resulting solution was subjected to vacuum distillation to remove the solvent contained therein, to obtain 0.30 g (yield: 92.0%) of intended 5,5-dimethyl-3-(3-ethoxy-1-methyl-5-trifluoromethyl-1H-pyrazol-4-ylmethylthio)-2-isoxazoline.

Workup

customto give rise
customto a reaction
customAfter the completion of the reaction
extractionfollowed by extraction with ethyl acetate
washThe resulting-organic layer was washed with an aqueous sodium chloride solution
dry with materialdried over anhydrous magnesium sulfate
distillationThe resulting solution was subjected to vacuum distillation
customto remove the solvent

Sources & evidence

ORD record: ord-86e446e160014b4bba636f6e14f86989
Source dataset: uspto-grants-2010_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07833939B2

Reaction notes

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