Benzenesulfonyl chloride → 1,5-Bis(benzenesulfonyl) carbohydrazide

HRID 2163307Notes

Reaction equation

HRID 2163307 reaction equation
[C:1]1([S:7](Cl)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH2:11][NH:12][C:13]([NH:15][NH2:16])=[O:14].C(=O)(O)[O-].[Na+]>C(O)C>[C:1]1([S:7]([NH:11][NH:12][C:13]([NH:15][NH:16][S:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)(=[O:9])=[O:8])=[O:14])(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 7369Benzenesulfonyl chlorideHCID 73948CarbohydrazideHCID 516892Sodium Bicarbonate

Product 1

HCID 706050231,5-Bis(benzenesulfonyl) carbohydrazide

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

175.6 g (1.0 mole) of benzenesulfonyl chloride was added to a stirred mixture of 45 g (0.5 mole) carbohydrazide and 100 g sodium bicarbonate in 1000 ml ethanol in a 3 liter 3 neck flask. The mixture was heated to gentle reflux for six hours. The cooled mixture was filtered and the solid precipitate (containing the desired product along with sodium chloride) was washed with ethanol and dried. Yield: 207 g. This mixture was then suspended in water and stirred for 10 minutes. The insoluble solid was filtered off and washed well with water and dried. Yield: 120.5 g, m.p. 227° C (dec.)

Workup

  1. temperatureThe mixture was heated
  2. temperatureto gentle reflux for six hours
  3. filtrationThe cooled mixture was filtered
  4. additionthe solid precipitate (containing the desired product along with sodium chloride)
  5. washwas washed with ethanol
  6. customdried
  7. filtrationThe insoluble solid was filtered off
  8. washwashed well with water
  9. customdried

Sources & evidence

ORD record
ord-ee625081b9d041b78aa4a0d462eff930
Source dataset
uspto-grants-1979_01
Patent number
US04133832

Reaction notes

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