Réaction #595315

Équation de réaction

4-[5-(3,5-dichlorophenyl)-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]-1-naphthalenecarboxamide

dimethylsulfoxide

trifluoroacetic anhydride

→

title product

4-[5-(3,5-dichlorophenyl)-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]-N-(dimethyl-λ4-sulfanylidene)-1-naphthalenecarboxamide

Solvants

dichloromethane

Conditions de réaction

Traitement

1. 1
   Températureto warm to −20° C. over 1 h
2. 2
   Autrequenched with water
3. 3
   Extractionextracted with dichloromethane
4. 4
   ExtractionThe combined organic extract
5. 5
   Lavagewas washed with aqueous 1.0 N of NaOH and brine
6. 6
   Séchagedried with anhydrous sodium sulfate
7. 7
   Concentrationconcentrated
8. 8
   AutreThe residue was purified by column chromatography on silica gel

Mode opératoire

To a stirred solution of dimethylsulfoxide (38 mg) in dichloromethane (1 mL) at −60° C. was added trifluoroacetic anhydride (105 mg). After the reaction mixture was stirred for 10 minutes at −60° C., a solution of 4-[5-(3,5-dichlorophenyl)-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]-1-naphthalenecarboxamide (75 mg, in 1.5 mL of dichloromethane and 0.4 mL of dimethylsulfoxide) was added. The reaction mixture was allowed to warm to −20° C. over 1 h, then quenched with water and extracted with dichloromethane. The combined organic extract was washed with aqueous 1.0 N of NaOH and brine, dried with anhydrous sodium sulfate and concentrated. The residue was purified by column chromatography on silica gel using dichloromethane/methanol (98:2 to 95:5) as eluent to afford the title product, a compound of the present invention, as semi-solid (70 mg, 82% yield).

Source