反应 #1869147

反应方程式

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

propanesulfonyl chloride

water

triethylamine

→

yellow crystals

收率 70.0%

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

收率 70.0%

溶剂

tetrahydrofuran

dichloromethane

反应条件

后处理

1. 1
   温度To the solution cooled
2. 2
   其他exceed 10° C
3. 3
   其他The organic layer was separated
4. 4
   洗涤washed with 150 g of water three times
5. 5
   浓缩The organic layer was concentrated in vacuum
6. 6
   workup.ADDITIONMethanol was added to the
7. 7
   浓缩concentrate for recrystallization
8. 8
   过滤followed by filtration
9. 9
   其他drying
10. 10
    其他There were obtained crude yellow crystals
11. 11
    其他The crude yellow crystals were purified by silica gel column chromatography (eluent, dichloromethane)
12. 12
    浓缩The elute was concentrated
13. 13
    其他followed by recrystallization from methanol, filtration
14. 14
    其他drying

实验过程

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%).

来源