Chlorosuccinimide → 5-[3,5-Bis(trifluoromethyl)phenyl]-3-(4-ethylphenyl)-5-trifluoromethyl-4,5-dihydroisoxazole

To a solution of 1.49 g of 4-ethylbenzaldoxime in 10 mL of N,N-dimethylformamide, 1.60 g of N-chlorosuccinimide was added and the resultant mixture was stirred at room temperature for 2 hours. Next, to the reaction mixture, 3.00 g of 3,5-bis(trifluoromethyl)-1-(1-trifluoromethylethenyl)benzene and 3.00 g of potassium hydrogen carbonate were added and the stirring of the resultant reaction mixture was continued at room temperature further for 14 hours. After the completion of the reaction, 10 mL of water was added to the reaction mixture and the resultant reaction mixture was extracted with ethyl acetate (50 mL×1). The organic phase was washed with 20 mL of water and then dehydrated and dried over saturated saline and anhydrous sodium sulfate in this order, and the solvent was distilled off under reduced pressure. To the resultant residue, hexane was added and a deposited crystal was filtered off to obtain 3.00 g of the objective substance as a white crystal.

1. customreaction mixture
2. additionwas added to the reaction mixture
3. customthe resultant reaction mixture
4. extractionwas extracted with ethyl acetate (50 mL×1)
5. washThe organic phase was washed with 20 mL of water
6. dry with materialdried over saturated saline and anhydrous sodium sulfate in this order
7. distillationthe solvent was distilled off under reduced pressure
8. additionTo the resultant residue, hexane was added
9. filtrationa deposited crystal was filtered off
10. customto obtain 3.00 g of the objective substance as a white crystal

ORD-Eintrag

ord-69471006fc5d4f5aa872d9264a881c9f

Quelldatensatz

uspto-grants-2012_11

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08318757B2