تفاعل #65222

معادلة التفاعل

4-Chloroacetophenone

5-Methylsulfonyl-3-(trifluoromethyl)isothiazole

acetic acid

→

title compound

1-(4-Chlorophenyl)-2-(3-(trifluoromethyl)-5-isothiazolyl)ethanone

المذيبات

tetrahydrofuran

ظروف التفاعل

المعالجة

1. 1
   أخرىThe oil of a 4.0 g (100 mmol) portion of 60 percent in mineral oil sodium hydride was removed by triple extraction with hexane
2. 2
   درجة الحرارةthe mixture was heated
3. 3
   درجة الحرارةat reflux
4. 4
   درجة الحرارةto cool
5. 5
   workup.ADDITIONwas added
6. 6
   درجة الحرارةthe mixture was heated
7. 7
   درجة الحرارةat reflux
8. 8
   workup.STIRRINGwith stirring for 3 hr
9. 9
   درجة الحرارةto cool
10. 10
    أخرىthe layers that formed
11. 11
    أخرىwere separated
12. 12
    استخلاصThe aqueous layer was extracted with 2×100 mL of ether
13. 13
    غسيلwashed with aqueous sodium bicarbonate solution
14. 14
    تجفيفdried over sodium sulfate
15. 15
    ترشيحfiltered
16. 16
    تركيزconcentrated by evaporation under reduced pressure
17. 17
    أخرىto obtain a residue
18. 18
    غسيلThis residue was washed with hexane
19. 19
    أخرىcrystallized from a 1:1 mixture of dichloromethane and hexane

الإجراء التجريبي

The oil of a 4.0 g (100 mmol) portion of 60 percent in mineral oil sodium hydride was removed by triple extraction with hexane and was replaced with 100 mL of tetrahydrofuran. 4-Chloroacetophenone (4.33 g, 28 mmol) was added and the mixture was heated at reflux with stirring for 1 hr and then allowed to cool. 5-Methylsulfonyl-3-(trifluoromethyl)isothiazole (4.57 g, 19.8 mmol) dissolved in a small amount of tetrahydrofuran was added and the mixture was heated at reflux with stirring for 3 hr and then allowed to cool. The mixture was next acidified with 60 mL of 10 percent aqueous acetic acid and the layers that formed were separated. The aqueous layer was extracted with 2×100 mL of ether and the organic fractions were combined, washed with aqueous sodium bicarbonate solution, dried over sodium sulfate, filtered, and concentrated by evaporation under reduced pressure to obtain a residue. This residue was washed with hexane and crystallized from a 1:1 mixture of dichloromethane and hexane to obtain 3.19 g (53 percent of theory) of the title compound as a solid melting at 109°-110° C.

المصدر