ChemicalBook CAS DataBase List pyroxasulfone

pyroxasulfone synthesis

8synthesis methods

Product Name:pyroxasulfone
CAS Number:447399-55-5
Molecular formula:C12H14F5N3O4S
Molecular Weight:391.31

Isoxazole, 3-[[[5-(difluoromethoxy)-1-methyl-3-(trifluoromethyl)-1H-pyrazol-4-yl]methyl]thio]-4,5-dihydro-5,5-dimethyl-

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Yield:447399-55-5 86%

Reaction Conditions:

with 3-chloro-benzenecarboperoxoic acid in chloroform at 0 - 20; for 4 h;

Steps:

46
PREPARATION EXAMPLE 46 Production of 3-(5-difluoromethoxy-1-methyl-3-trifluoromethyl-1H-pyrazol-4-ylmethanesulfonyl)-5,5-dimethyl-2-isoxazoline (Present Compound No. 3-0188); 157.6 g of m-chloroperbenzoic acid (purity: 70%, 0.64 mole) was added, with ice-cooling, to a solution of 56.5 g (0.16 mole) of 3-(5-difluoromethoxy-1-methyl-3-trifluoromethyl-1H-pyrazol-4-ylmethylthio)-5,5-dimethyl-2-isoxazoline dissolved in 1000 ml of chloroform. The mixture was stirred at room temperature for 4 hours to give rise to a reaction. After the completion of the reaction, the reaction solution was filtrated to remove insoluble matters. The filtrate thus obtained was poured into ice water, followed by extraction with chloroform. The resulting organic layer was washed with a 10% aqueous sodium hydroxide solution, water, an aqueous sodium hydrogensulfite solution, and a saturated aqueous sodium chloride solution in this order and then dried over anhydrous magnesium sulfate. The resulting solution was subjected to vacuum distillation to remove the solvent contained therein. The residue was washed with n-hexane to obtain 52.7 g (yield: 86.0%) of 3-(5-difluoromethoxy-1-methyl-3-trifluoromethyl-1H-pyrazol-4-ylmethanesulfonyl)-5,5-dimethyl-2-isoxazoline as white crystals (melting point: 129.0 to 130.0° C.). ¹H-NMR [CDCl₃/TMS, δ (ppm)]: 6.83 (1H,t,J=71.9 Hz), 4.60 (2H,s), 3.88 (3H,s), 3.11 (2H,s), 1.52 (6H,s)

References:

Takahashi, Satoru;Ueno, Ryohei;Yamaji, Yoshihiro;Fujinami, Makoto US2005/256004, 2005, A1 Location in patent:Page/Page column 26

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