3-(1-tert-butyl-5-chloro-3-trifluoromethyl-1H-pyrazol-4-ylmethylthio)-5,5-dimethyl-2-isoxazoline → HCID 178427280, compound

HRID 1172065Notes

Reaction equation

C([N:5]1[C:9]([Cl:10])=[C:8]([CH2:11][S:12][C:13]2[CH2:17][C:16]([CH3:19])([CH3:18])[O:15][N:14]=2)[C:7]([C:20]([F:23])([F:22])[F:21])=[N:6]1)(C)(C)C.Br.C(O)(=O)C>O>[Cl:10][C:9]1[NH:5][N:6]=[C:7]([C:20]([F:21])([F:23])[F:22])[C:8]=1[CH2:11][S:12][C:13]1[CH2:17][C:16]([CH3:19])([CH3:18])[O:15][N:14]=1

Participants

Conditions

Temperature: 45 °C

Procedure

19.8 g (53.4 mmoles) of 3-(1-tert-butyl-5-chloro-3-trifluoromethyl-1H-pyrazol-4-ylmethylthio)-5,5-dimethyl-2-isoxazoline was added to 170 ml of a 25% hydrogen bromide-acetic acid solution. The mixture was stirred at 40 to 50° C. for 2 hours to give rise to a reaction. After the completion of the reaction was confirmed, 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 12.0 g (yield: 60.6%) of 3-(5-chloro-3-trifluoromethyl-1H-pyrazol-4-ylmethylthio)-5,5-dimethyl-2-isoxazoline as light yellow crystals (melting point: 120.0 to 122.0° C.).

Workup

customto give rise
customto a 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-34bf047967b34187a1f6662c3e818df5
Source dataset: uspto-grants-2010_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07833939B2

Reaction notes

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