Hydrazine → HCID 67598281, compound

HRID 1417312Notes

Reaction equation

HRID 1417312 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][CH2:12][CH2:13][CH2:14][CH2:15][O:16][C:17]2[CH:22]=[CH:21][C:20]([N+:23]([O-])=O)=[CH:19][CH:18]=2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.NN>C(O)C.[Pd]>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([S:8]([NH:11][CH2:12][CH2:13][CH2:14][CH2:15][O:16][C:17]2[CH:18]=[CH:19][C:20]([NH2:23])=[CH:21][CH:22]=2)(=[O:9])=[O:10])=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 9321HydrazineHCID 67600028HCID 67600028, compound

Product 1

HCID 67598281HCID 67598281, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

5.0 g of 4-methyl-N-[4-(4-nitrophenoxy)-butyl]benzenesulfonamide (Example 35) is dissolved in 500 ml of ethanol, 1.5 ml of anhydrous hydrazine and 500 mg of 10% palladium on carbon are added, and the mixture is then stirred under reflux for four hours. The reaction mixture is filtered hot. Cooling the filtrate to room temperature produces a precipitate, which is collected. The filtrate is reheated to boiling and utilized to re-extract the palladium-carbon residue, and after filtration, cooled to room temperature, the precipitate being collected. The process is repeated until no further precipitate is formed on cooling to room temperature. After drying at 60° in vacuo, the combined precipitates weigh 3.3 g; m.p. 176°-178° C.

Workup

  1. temperatureunder reflux for four hours
  2. filtrationThe reaction mixture is filtered hot
  3. customproduces a precipitate, which
  4. customis collected
  5. extractionto re-extract the palladium-carbon residue
  6. filtrationafter filtration
  7. temperaturecooled to room temperature
  8. customthe precipitate being collected
  9. customis formed
  10. temperatureon cooling to room temperature
  11. customAfter drying at 60° in vacuo
  12. customthe combined precipitates

Sources & evidence

ORD record
ord-2a1beb848f1d4d95b7d5eacdf0a8b46b
Source dataset
uspto-grants-1999_03
Patent number
US05877196

Reaction notes

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