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

HRID 127966Notes

Reaction equation

HRID 127966 reaction equation
[C:1]1([NH:7][NH:8][C:9](=[O:21])[C:10]2[CH:15]=[CH:14][C:13]([Cl:16])=[C:12]([S:17](=[O:20])(=[O:19])[NH2:18])[CH:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[I-].[K+].[CH2:24](Br)[CH:25]=[CH2:26]>C(O)(C)C>[CH2:26]([N:7]([C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)[NH:8][C:9](=[O:21])[C:10]1[CH:15]=[CH:14][C:13]([Cl:16])=[C:12]([S:17](=[O:20])(=[O:19])[NH2:18])[CH:11]=1)[CH:25]=[CH2:24]

Participants

5

Reactant 3

HCID 4875Potassium IodideHCID 7841Allyl bromideHCID 155715011-Phenyl-2-(3-sulfamoyl-4-chlorobenzoyl)-hydrazine

Product 1

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

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

In a three necked 12 liter round bottom reaction flask equipped with a mechanical stirrer and reflux condenser was placed isopropanol 6.1 liters and 1-phenyl-2-(3-sulfamoyl-4-chlorobenzoyl)-hydrazine 1.3 kg (4.1 mol), potassium iodide 68.0 g (0.41 mol) and allyl bromide 768 g (8 mol). This mixture was stirred at gentle reflux for about 20 hours then suction filtered while still hot. The cake was washed with isopropanol 300 ml and the combined filtrate and wash were diluted with warm water 2.7 liters. Crystallization occured in about 0.5 hours. The crystals were filtered and washed with isopropanol-water (70% v/v) to provide the compound (m.p. 99°-101° C.).

Workup

  1. customIn a three necked 12 liter round bottom reaction flask equipped with a mechanical stirrer
  2. temperaturereflux condenser
  3. temperatureat gentle reflux for about 20 hours
  4. filtrationsuction filtered while still hot
  5. washThe cake was washed with isopropanol 300 ml
  6. washthe combined filtrate and wash
  7. additionwere diluted with warm water 2.7 liters
  8. customCrystallization
  9. filtrationThe crystals were filtered
  10. washwashed with isopropanol-water (70% v/v)

Sources & evidence

ORD record
ord-8daef974bced459fb9a7bad44996d53f
Source dataset
uspto-grants-1981_03
Patent number
US04258059

Reaction notes

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