반응 #1869147

반응 방정식

(3-(hydroxy)imino-3H-thiophen-2-ylidene)-(2-methylphenyl)-acetonitrile

propanesulfonyl chloride

water

triethylamine

→

yellow crystals

수율 70.0%

(3-(propanesulfonyloxy)imino-3H-thiophen-2-ylidene)-(2-methylphenyl)-acetonitrile

수율 70.0%

용매

tetrahydrofuran

dichloromethane

반응 조건

후처리

1. 1
   온도To the solution cooled
2. 2
   기타exceed 10° C
3. 3
   기타The organic layer was separated
4. 4
   세척washed with 150 g of water three times
5. 5
   농축The organic layer was concentrated in vacuum
6. 6
   workup.ADDITIONMethanol was added to the
7. 7
   농축concentrate for recrystallization
8. 8
   여과followed by filtration
9. 9
   기타drying
10. 10
    기타There were obtained crude yellow crystals
11. 11
    기타The crude yellow crystals were purified by silica gel column chromatography (eluent, dichloromethane)
12. 12
    농축The elute was concentrated
13. 13
    기타followed by recrystallization from methanol, filtration
14. 14
    기타drying

실험 절차

In 490 g of tetrahydrofuran were dissolved 45 g (0.19 mol) of (3-(hydroxy)imino-3H-thiophen-2-ylidene)-(2-methylphenyl)-acetonitrile in Synthesis Example 1 and 27.0 g (0.19 mol) of commercially available propanesulfonyl chloride. To the solution cooled, 20.6 g (0.20 mol) of triethylamine was added dropwise such that the temperature might not exceed 10° C. The solution was allowed to ripen for 1 hour at room temperature, after which 150 g of water and 500 g of dichloromethane were added. The organic layer was separated, and washed with 150 g of water three times. The organic layer was concentrated in vacuum. Methanol was added to the concentrate for recrystallization, followed by filtration and drying. There were obtained crude yellow crystals. The crude yellow crystals were purified by silica gel column chromatography (eluent, dichloromethane). The elute was concentrated, followed by recrystallization from methanol, filtration and drying. There was obtained 77 g of yellow crystals (yield 70%).

출처