Sulfisoxazole → 4-Benzylamino-N-(3,4-dimethyl-5-isoxazolyl)benzenesulfonamide

HRID 1899686

反応式

HRID 1899686 の反応式
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][C:12]2[O:16][N:15]=[C:14]([CH3:17])[C:13]=2[CH3:18])(=[O:10])=[O:9])=[CH:4][CH:3]=1.C(=O)(O)[O-].[Na+].[CH2:24](Br)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>C(O)C>[CH2:24]([NH:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][C:12]2[O:16][N:15]=[C:14]([CH3:17])[C:13]=2[CH3:18])(=[O:10])=[O:9])=[CH:4][CH:3]=1)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

参加物

5

反応物 3

HCID 5344SulfisoxazoleHCID 7498Benzyl BromideHCID 516892Sodium Bicarbonate

生成物 1

HCID 100212404-Benzylamino-N-(3,4-dimethyl-5-isoxazolyl)benzenesulfonamide収率 72%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

反応条件

温度
70 °C

実験手順

To a mixture of 4-amino-N-(3,4-dimethyl-5-isoxazolyl)benzenesulfonamide (1.0 g, 3.74 mmol) and sodium bicarbonate (310 mg, 4.48 mmol) suspended in ethanol was added benzyl bromide (770 mg, 4.48 mmol). After 10 min of stirring at 70° C., the mixture became homogeneous. The reaction was stirred at 70° C. for 2 h and the solvent and volatiles were evaporated under reduced pressure. The residue was dissolved in ethyl acetate and washed with brine (2×25 ml). After drying over magnesium sulfate, evaporation of the solvent left a viscous yellow oil which was chromatographed on silica gel to give 960 mg (72% yield) clear, colorless oil. Further purification by HPLC gave a white solid, m.p. 47°-8° C.

後処理

  1. stirringThe reaction was stirred at 70° C. for 2 h
  2. customthe solvent and volatiles were evaporated under reduced pressure
  3. dissolutionThe residue was dissolved in ethyl acetate
  4. washwashed with brine (2×25 ml)
  5. dry with materialAfter drying over magnesium sulfate, evaporation of the solvent
  6. waitleft a viscous yellow oil which
  7. customwas chromatographed on silica gel
  8. customto give 960 mg (72% yield) clear
  9. customFurther purification by HPLC
  10. customgave a white solid, m.p. 47°-8° C.

出典と根拠

ORDレコード
ord-7fc3d170a6f8405bb785bca560b17f29
出典データセット
uspto-grants-1996_11
特許番号
US05571821

関連ノート

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