Water → 2'-Nitro-4'-methylthio-p-toluenesulfonanilide

HRID 1356674노트

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HRID 1356674 반응식
[N+:1]([C:4]1[CH:20]=[C:19]([S:21][C:22]#N)[CH:18]=[CH:17][C:5]=1[NH:6][S:7]([C:10]1[CH:15]=[CH:14][C:13]([CH3:16])=[CH:12][CH:11]=1)(=[O:9])=[O:8])([O-:3])=[O:2].[BH4-].[Na+].CI.O>CO>[N+:1]([C:4]1[CH:20]=[C:19]([S:21][CH3:22])[CH:18]=[CH:17][C:5]=1[NH:6][S:7]([C:10]1[CH:11]=[CH:12][C:13]([CH3:16])=[CH:14][CH:15]=1)(=[O:9])=[O:8])([O-:3])=[O:2]

참가 물질

6

반응물 4

HCID 962WaterHCID 6328Methyl iodideHCID 4311764Sodium borohydrideHCID 185092522'-Nitro-4'-thiocyano-p-toluenesulfonanilide

생성물 1

HCID 185093012'-Nitro-4'-methylthio-p-toluenesulfonanilide수율 47%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

To a solution of 2′-Nitro-4′-thiocyano-p-toluenesulfonanilide (5.0 g (14.3 mmol) in methanol (20 ml), sodium borohydride (2.80 g (66.7 mmol)) was added under cooling with ice and with stirring. After 30 minutes' stirring, to the resulting mixture, methyl iodide (3.67 ml (59.0 mmol)) was added dropwise under cooling with ice and the mixture was then stirred at room temperature for 20 hours. Then, water was added to the reaction mixture and the resulting mixture was extracted with ethyl acetate. The extract was washed with a saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate, filtered and concentrated. The residue was then subjected to silica gel column chromatography with ethyl acetate-hexane (1:4) as eluent. The resulting crystals were recrystallized from ethyl acetate to give 2.27 g (47%) of 2′-nitro-4′-methylthio-p-toluenesulfonanilide as orange crystals.

후처리

  1. temperatureunder cooling with ice
  2. additionwas added dropwise
  3. temperatureunder cooling with ice
  4. stirringthe mixture was then stirred at room temperature for 20 hours
  5. extractionthe resulting mixture was extracted with ethyl acetate
  6. washThe extract was washed with a saturated aqueous solution of sodium chloride
  7. dry with materialdried over anhydrous magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customThe resulting crystals were recrystallized from ethyl acetate

출처 및 근거

ORD 기록
ord-6715ceead43145bdaed3549a1d8ea711
출처 데이터셋
uspto-grants-2003_07
특허 번호
US06586617B1

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