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

HRID 1589419노트

반응식

HRID 1589419 반응식
[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]

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 3776Isopropanol용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-db21313f16aa4ec1a3502f319105b778
출처 데이터셋
uspto-grants-1986_02
특허 번호
US04570001

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