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

HRID 1589419Notes

Reaction equation

HRID 1589419 reaction equation
[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]

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-db21313f16aa4ec1a3502f319105b778
Source dataset
uspto-grants-1986_02
Patent number
US04570001

Reaction notes

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