反应详情

温度

0 °C

To a cooled (0° C.), stirred solution of 21.3 g (0.10 mol) of 2-octyl-4-isothiazolin-3-one in 400 ml of anhydrous ethyl ether was added dropwise 30 ml (0.03 mol) of a 1.0M solution of lithium aluminum hydride in tetrahydrofuran over a 20 min period. After the addition the mixture was stirred at 0° C. for 1 hr. Over a 15 min period 8.96 ml (0.10 mol) of propionyl chloride was added. After this addition the mixture was allowed to warm to room temperature. After 12 hr the reaction mixture was a white solid suspended in an orange solution. The mixture was filtered and the filtrate was diluted with 300 ml of ethyl acetate and washed once with 300 ml of 10% aqueous hydrochloric acid. The organic layer was set aside and the aqueous layer was extracted three times with ethyl acetate. The combined organic layers were washed with water until the washes were neutral in pH, washed with brine, and dried over anhydrous magnesium sulfate. Filtration and removal of solvents gave N-octyl-cis-3-(propanoylthio)acrylamide as an oil which crystallized upon standing. These crude crystals were recrystallized from ethyl ether/hexane to give 16 g (59% yield) as white crystals, m.p. 68°-70° C., and is reported in Table 1.

1. additionAfter the addition the mixture
2. additionAfter this addition the mixture
3. temperatureto warm to room temperature
4. waitAfter 12 hr the reaction mixture was
5. filtrationThe mixture was filtered
6. additionthe filtrate was diluted with 300 ml of ethyl acetate
7. washwashed once with 300 ml of 10% aqueous hydrochloric acid
8. extractionthe aqueous layer was extracted three times with ethyl acetate
9. washThe combined organic layers were washed with water until the washes
10. washwashed with brine
11. dry with materialdried over anhydrous magnesium sulfate
12. filtrationFiltration and removal of solvents