Water → N-Ethyl-4'-methylthio-2'-nitro-p-toluenesulfonanilide

HRID 1356675노트

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HRID 1356675 반응식
[H-].[Na+].[N+:3]([C:6]1[CH:22]=[C:21]([S:23][CH3:24])[CH:20]=[CH:19][C:7]=1[NH:8][S:9]([C:12]1[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][CH:13]=1)(=[O:11])=[O:10])([O-:5])=[O:4].[CH2:25](I)[CH3:26].O>CN(C=O)C>[CH2:25]([N:8]([S:9]([C:12]1[CH:13]=[CH:14][C:15]([CH3:18])=[CH:16][CH:17]=1)(=[O:11])=[O:10])[C:7]1[CH:19]=[CH:20][C:21]([S:23][CH3:24])=[CH:22][C:6]=1[N+:3]([O-:5])=[O:4])[CH3:26]

참가 물질

6

반응물 4

HCID 962WaterHCID 6340IodoethaneHCID 24758Sodium hydrideHCID 185093012'-Nitro-4'-methylthio-p-toluenesulfonanilide

생성물 1

HCID 18509310N-Ethyl-4'-methylthio-2'-nitro-p-toluenesulfonanilide수율 64.1%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a suspension of sodium hydride (65%, 0.21 g (5.76 mmol)) in 4.0 ml of DMF, 2′-nitro-4′-methylthio-p-toluenesulfonanilide (1.50 g (4.43 mmol)) was added with stirring at room temperature. To the resulting mixture, after 30 minutes' stirring at room temperature, ethyl iodide (0.52 ml (6.21 mmol)) was added dropwise and the mixture was stirred at room temperature for 16 hours. Then, the reaction mixture was poured into water and extracted with ethyl acetate. The extract was washed with a saturated aqueous solution of sodium bicarbonate, dilute hydrochloric acid, and saturated aqueous solution of sodium chloride successively. The ethyl acetate layer was dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The resulting residue was then subjected to silica gel column chromatography with chloroform as eluent to give 1.04 g (64%) of the title compound as pale yellow crystals.

후처리

  1. additionwas added
  2. stirringTo the resulting mixture, after 30 minutes' stirring at room temperature
  3. stirringthe mixture was stirred at room temperature for 16 hours
  4. extractionextracted with ethyl acetate
  5. washThe extract was washed with a saturated aqueous solution of sodium bicarbonate, dilute hydrochloric acid, and saturated aqueous solution of sodium chloride successively
  6. dry with materialThe ethyl acetate layer was dried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-080e41be164a44c790283355840931f1
출처 데이터셋
uspto-grants-2003_07
특허 번호
US06586617B1

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