반응 #930

반응 방정식

water

2-nitro-6-(phenylthio)benzonitrile

SnCl2

→

2-Amino-6-(phenylthio)benzonitrile

용매

diglyme

HCl

반응 조건

후처리

1. 1
   기타The water bath was removed
2. 2
   workup.STIRRINGthe reaction was stirred at room temperature for 0.5 h
3. 3
   workup.ADDITIONThis reaction mixture was poured into
4. 4
   workup.STIRRINGa vigorously stirring
5. 5
   workup.ADDITIONmixture of 100 mL of 50% NaOH and 300 g of crushed ice
6. 6
   여과Precipitate was collected by filtration
7. 7
   세척washed with 1N NaOH and water
8. 8
   기타Purification by flash column chromatography on silica gel with methylene chloride
9. 9
   기타resulted in 2.3 g (68%) of 2-amino-6-(phenylthio)benzonitrile as a white solid

실험 절차

To a water bath-cooled solution of 3.9 g (0.015 mol) of 2-nitro-6-(phenylthio)benzonitrile (Example 1) in 85 mL of diglyme was added dropwise, with stirring, 11.53 g (0.045 mol) of SnCl2.2H2 O in 35 mL of conc. HCl. The water bath was removed, and the reaction was stirred at room temperature for 0.5 h. This reaction mixture was poured into a vigorously stirring mixture of 100 mL of 50% NaOH and 300 g of crushed ice. Precipitate was collected by filtration and washed with 1N NaOH and water. Purification by flash column chromatography on silica gel with methylene chloride resulted in 2.3 g (68%) of 2-amino-6-(phenylthio)benzonitrile as a white solid: mp 73°-77° C.

출처