Water → Benzonitrile, 2-amino-6-(phenylthio)-

HRID 834

반응식

HRID 834 반응식
O.[N+:2]([C:5]1[CH:12]=[CH:11][CH:10]=[C:9]([S:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:6]=1[C:7]#[N:8])([O-])=O.Cl[Sn]Cl>COCCOCCOC.Cl>[NH2:2][C:5]1[CH:12]=[CH:11][CH:10]=[C:9]([S:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:6]=1[C:7]#[N:8]

참가 물질

6

반응물 3

HCID 962WaterHCID 24479Stannous ChlorideHCID 151982412-Nitro-6-(phenylthio)benzonitrile

생성물 1

HCID 486276Benzonitrile, 2-amino-6-(phenylthio)-

시약·촉매·용매 2

HCID 313Hydrochloric Acid용매HCID 8150Diglyme용매

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.

후처리

  1. customThe water bath was removed
  2. stirringthe reaction was stirred at room temperature for 0.5 h
  3. additionThis reaction mixture was poured into
  4. stirringa vigorously stirring
  5. additionmixture of 100 mL of 50% NaOH and 300 g of crushed ice
  6. filtrationPrecipitate was collected by filtration
  7. washwashed with 1N NaOH and water
  8. customPurification by flash column chromatography on silica gel with methylene chloride
  9. customresulted in 2.3 g (68%) of 2-amino-6-(phenylthio)benzonitrile as a white solid

출처 및 근거

ORD 기록
ord-d850da0197e245649bff3ba3999f661f
출처 데이터셋
uspto-grants-1998_03
특허 번호
US05723452

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