Water → HCID 17862867, compound

HRID 1172075Notes

Reaction equation

[C-:1]#[N:2].[Na+].[CH3:4][C:5]1([CH3:23])[O:9][N:8]=[C:7]([S:10][CH2:11][C:12]2[C:13]([C:19]([F:22])([F:21])[F:20])=[N:14][N:15]([CH3:18])[C:16]=2F)[CH2:6]1.O>CN(C)C=O>[C:1]([C:16]1[N:15]([CH3:18])[N:14]=[C:13]([C:19]([F:22])([F:21])[F:20])[C:12]=1[CH2:11][S:10][C:7]1[CH2:6][C:5]([CH3:23])([CH3:4])[O:9][N:8]=1)#[N:2]

Participants

Conditions

Temperature: 40 °C

Procedure

0.2 g (4.0 mmoles) of sodium cyanide was added to a solution of 0.5 g (1.6 mmoles) of 5,5-dimethyl-3-(5-fluoro-1-methyl-3-trifluoromethyl-1H-pyrazol-4-ylmethylthio)-2-isoxazoline dissolved in 30 ml of N,N-dimethylformamide. The mixture was stirred at 40° C. for 1 hour to give rise to a reaction. After confirmation of 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 water and 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 0.9 g of crude 3-(5-cyano-1-methyl-3-trifluoromethyl-1H-pyrazol-4-ylmethylthio)-5,5-dimethyl-2-isoxazoline as a yellow oily substance.

Workup

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

Sources & evidence

ORD record: ord-21f4605c6bde404dbdde236b99bdb6dd
Source dataset: uspto-grants-2010_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07833939B2

Reaction notes

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