反应详情

温度

55 °C

A suspension of zinc (22.94 g, 0.35 mol) and 2-acetylamino-indan-5-sulfonyl chloride (93% weight) (29.45 g, 0.10 mol) in acetonitrile (200 mL) in a 1 Liter four-necked round-bottomed flask equipped with a condenser, a thermometer, an addition funnel, and a mechanical stirrer was heated to about 50-60° C. The heating source was removed and to the warm suspension was added concentrated HCl (59.20 g, 0.60 mol) slowly over 1 hour. The addition rate was adjusted to maintain the reaction temperature between about 70-75° C. A gentle gas (H2) evolution was observed throughout the addition of HCl. The reaction was then cooled to about 30-36° C. over 30 minutes while stirring. The reaction mixture was filtered into a 500 mL one-necked round-bottomed flask through a fritted glass funnel to remove the Zn residue. The reaction flask was rinsed with EtOAc (25 mL). The mixture was concentrated on a rotavapor under reduced pressure at about 45-50° C. bath temperature to remove most of the organic solvents. The concentrated aqueous solution was mixed with of EtOAc (150 mL), followed by the addition of H2O (75 mL). After stirring for 15 minutes, the layers were separated. The organic layer was washed four times with H2O (3×75 mL). After separation of layers, the organic layer was concentrated on a rotavapor at 60° C. to ¼ of its original volume (about 40 mL). Most of the precipitated white solid was dissolved by heating to reflux. The mixture was then diluted with MTBE (75 mL). The mixture was stirred at ambient temperature for 18 hours. The solid product was collected by vacuum filtration, washed with MTBE (20 mL), dried under nitrogen for 4 hours, then in a vacuum oven at about 40-45° C. for 24 h. The product was obtained as an off-white solid.

1. customequipped with a condenser
2. customThe heating source was removed and to the warm suspension
3. temperatureto maintain the reaction temperature between about 70-75° C
4. temperatureThe reaction was then cooled to about 30-36° C. over 30 minutes
5. filtrationThe reaction mixture was filtered into a 500 mL one-necked round-bottomed flask through a fritted glass funnel
6. customto remove the Zn residue
7. washThe reaction flask was rinsed with EtOAc (25 mL)
8. concentrationThe mixture was concentrated on a rotavapor under reduced pressure at about 45-50° C. bath temperature
9. customto remove most of the organic solvents
10. additionThe concentrated aqueous solution was mixed with of EtOAc (150 mL)
11. additionfollowed by the addition of H2O (75 mL)
12. stirringAfter stirring for 15 minutes
13. customthe layers were separated
14. washThe organic layer was washed four times with H2O (3×75 mL)
15. customAfter separation of layers
16. concentrationthe organic layer was concentrated on a rotavapor at 60° C.
17. dissolutionMost of the precipitated white solid was dissolved
18. temperatureby heating to reflux
19. additionThe mixture was then diluted with MTBE (75 mL)
20. stirringThe mixture was stirred at ambient temperature for 18 hours
21. filtrationThe solid product was collected by vacuum filtration
22. washwashed with MTBE (20 mL)
23. customdried under nitrogen for 4 hours
24. customThe product was obtained as an off-white solid