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

HRID 1356674ノート

反応式

HRID 1356674 の反応式
[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]

参加物

6

反応物 4

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

生成物 1

HCID 185093012'-Nitro-4'-methylthio-p-toluenesulfonanilide収率 47%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-6715ceead43145bdaed3549a1d8ea711
出典データセット
uspto-grants-2003_07
特許番号
US06586617B1

反応ノート

読み込み中…