Potassium Iodide → 1-Allyl-1-phenyl-2-(3-sulfamoyl-4-chlorobenzoyl)-hydrazine

HRID 1589419ノート

反応式

HRID 1589419 の反応式
[NH2:1][S:2]([C:5]1[CH:6]=[C:7]([CH:12]=[CH:13][C:14]=1[Cl:15])[C:8]([NH:10][NH2:11])=[O:9])(=[O:4])=[O:3].C(=O)(O)[O-].[Na+].[I-].[K+].[CH2:23](Br)[CH:24]=[CH2:25]>C(O)(C)C>[CH2:23]([N:11]([C:5]1[CH:6]=[CH:7][CH:12]=[CH:13][CH:14]=1)[NH:10][C:8](=[O:9])[C:7]1[CH:12]=[CH:13][C:14]([Cl:15])=[C:5]([S:2](=[O:4])(=[O:3])[NH2:1])[CH:6]=1)[CH:24]=[CH2:25]

参加物

6

反応物 4

HCID 4875Potassium IodideHCID 7841Allyl bromideHCID 516892Sodium BicarbonateHCID 24026562-Chloro-5-(hydrazinecarbonyl)benzene-1-sulfonamide

生成物 1

HCID 155715021-Allyl-1-phenyl-2-(3-sulfamoyl-4-chlorobenzoyl)-hydrazine収率 80%

試薬・触媒・溶媒 1

HCID 3776Isopropanol溶媒

実験手順

A mixture of 3-aminosulfonyl-4-chloro-benzhydrazide (326.6g, 1.0 mole) sodium bicarbonate (420.0g, 2.0 mole), potassium iodide (16.6g, 0.1 mole) and allyl bromide (242.0g, 2.0 mole) in isopropanol (1,500 ml) was stirred at gentle reflux for 20 hours, then cooled to 50° and filtered by suction. The cake was washed twice with 100 ml portions of isopropanol. The washes and filtrate were combined and diluted with sufficient water to make a 70% isopropanol solution, then allowed to stir overnight to complete crystallization. The crude product was filtered and washed twice with 100 ml portions of isopropanol-water (70:30). One recrystallization from isopropanol-water (70:30) and clarification with activated charcoal gave pure compound in 80% yield.

後処理

  1. temperatureat gentle reflux for 20 hours
  2. temperaturecooled to 50°
  3. filtrationfiltered by suction
  4. washThe cake was washed twice with 100 ml portions of isopropanol
  5. additiondiluted with sufficient water
  6. stirringto stir overnight
  7. customcrystallization
  8. filtrationThe crude product was filtered
  9. washwashed twice with 100 ml portions of isopropanol-water (70:30)
  10. customOne recrystallization from isopropanol-water (70:30) and clarification with activated charcoal
  11. customgave pure compound in 80% yield

出典と根拠

ORDレコード
ord-db21313f16aa4ec1a3502f319105b778
出典データセット
uspto-grants-1986_02
特許番号
US04570001

反応ノート

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