Water → N-(2-Methoxyphenyl)-4-methylbenzenesulfonamide

HRID 2407

反応式

HRID 2407 の反応式
[CH3:1][O:2][C:3]1[C:4]([NH2:9])=[CH:5][CH:6]=[CH:7][CH:8]=1.N1C=CC=CC=1.[C:16]1([CH3:26])[CH:21]=[CH:20][C:19]([S:22](Cl)(=[O:24])=[O:23])=[CH:18][CH:17]=1.O>C1(C)C=CC=CC=1.CN(C)C1C=CN=CC=1>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[NH:9][S:22]([C:19]1[CH:20]=[CH:21][C:16]([CH3:26])=[CH:17][CH:18]=1)(=[O:24])=[O:23]

参加物

7

反応物 4

HCID 962WaterHCID 1049PyridineHCID 70002-MethoxyanilineHCID 73974-Toluenesulfonyl chloride

生成物 1

HCID 241731N-(2-Methoxyphenyl)-4-methylbenzenesulfonamide収率 62%

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 1140Toluene溶媒

実験手順

o-Anisidine (2.34 ml, 20 mmol) was dissolved in toluene (60 ml) to which were subsequently added, with cooling in an ice bath, pyridine (4.58 ml, 60 mmol), p-toluenesulfonyl chloride (3.89 g, 20 mmol) and a catalytically effective amount of 4-dimethylaminopyridine. After 2.5 hours of stirring at room temperature, the resulting reaction solution was mixed-with water (50 ml), extracted with ethyl acetate and then washed with water, 10% sodium hydroxide aqueous solution, 1N hydrochloric acid, water and saturated brine in that order. After drying on anhydrous magnesium sulfate and removing the solvent by evaporation, the resulting orange solid was dissolved in ethyl acetate (50 ml), adsorbed to anhydrous magnesium sulfate (20 g), eluted with ether and then subjected to evaporation to remove the solvent. The resulting colorless solid which was then washed with an ether-hexane (1:1) mixture solution to obtain 3.44 g (62.0%) of the title compound in the form of colorless prism crystals.

後処理

  1. additionwere subsequently added
  2. temperaturewith cooling in an ice bath
  3. customthe resulting reaction solution
  4. extractionextracted with ethyl acetate
  5. washwashed with water, 10% sodium hydroxide aqueous solution, 1N hydrochloric acid, water and saturated brine in that order
  6. dry with materialAfter drying on anhydrous magnesium sulfate
  7. customremoving the solvent
  8. customby evaporation
  9. dissolutionthe resulting orange solid was dissolved in ethyl acetate (50 ml)
  10. washeluted with ether
  11. customsubjected to evaporation
  12. customto remove the solvent
  13. washThe resulting colorless solid which was then washed with an ether-hexane (1:1) mixture solution

出典と根拠

ORDレコード
ord-04e2e891f8e24233803e97b3a1a02cf4
出典データセット
uspto-grants-1998_03
特許番号
US05728835

関連ノート

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