Ethanol → HCID 20262153, compound

HRID 464621Notes

Reaction equation

HRID 464621 reaction equation
C(O)C.[Cl:4][C:5]1[CH:6]=[C:7]([S:12]([NH:15][C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([OH:22])[CH:17]=2)(=[O:14])=[O:13])[CH:8]=[N:9][C:10]=1Cl.[NH2:23][NH2:24]>O>[Cl:4][C:5]1[CH:6]=[C:7]([S:12]([NH:15][C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([OH:22])[CH:17]=2)(=[O:14])=[O:13])[CH:8]=[N:9][C:10]=1[NH:23][NH2:24]

Participants

5

Reactant 3

HCID 702EthanolHCID 9321HydrazineHCID 20262152HCID 20262152, compound

Product 1

HCID 20262153HCID 20262153, compoundYield 80.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 500 ml ethanol was added 5,6-dichloro-3'-hydroxy-3-pyridinesulfonanilide (10.4 g, 42 mmol) and 95 percent hydrazine (60 mmol). The reaction mixture was refluxed overnight. The completely reacted mixture was chilled, and the precipitate was filtered off and washed with ethanol. The filtrate was concentrated so as to obtain a second crop, yielding a total of 16.5 g. The solid was stirred in 250 ml of water to remove any salts. The product was filtered, washed with water, and dried under vacuum at 50° C. to give 10.61 g (80 percent) of pure product.

Workup

  1. temperatureThe reaction mixture was refluxed overnight
  2. temperatureThe completely reacted mixture was chilled
  3. filtrationthe precipitate was filtered off
  4. washwashed with ethanol
  5. concentrationThe filtrate was concentrated so as
  6. customto obtain a second crop
  7. customyielding a total of 16.5 g
  8. customto remove any salts
  9. filtrationThe product was filtered
  10. washwashed with water
  11. customdried under vacuum at 50° C.

Sources & evidence

ORD record
ord-e19d0bb152324936ab94aef6ed694d91
Source dataset
uspto-grants-1985_10
Patent number
US04548888

Reaction notes

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