Hydrazine hydrate (1:1) → HCID 68678931, compound

HRID 2240070Notes

Reaction equation

HRID 2240070 reaction equation
[C:1]1([S:7]([CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([O:17][CH2:18][CH2:19][Cl:20])[C:12]=2[N+:21]([O-])=O)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.O.NN>C(O)C.[Pd]>[C:1]1([S:7]([CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([O:17][CH2:18][CH2:19][Cl:20])[C:12]=2[NH2:21])(=[O:9])=[O:8])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 68679897HCID 68679897, compound

Product 1

HCID 68678931HCID 68678931, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 1-benzenesulfonylmethyl-3-(2-chloro-ethoxy)-2-nitrobenzene (0.57 g, 1.6 mmoles) in ethanol (10 mL) was stirred under nitrogen in a round bottom flask at 60° C. 10% Pd/C was added, and the temperature was increased to 80° C. Hydrazine hydrate (1.5 mL) was added dropwise and the mixture was stirred at reflux for 3 hours. Reaction mixture was filtered off through Celite, and the solution was washed with H2O (3×), dried over Na2SO4, and concentrated under vacuum to afford the title compound as an off white solid (0.5 g, 1.53 mmoles).

Workup

  1. temperaturethe temperature was increased to 80° C
  2. stirringthe mixture was stirred
  3. temperatureat reflux for 3 hours
  4. customReaction mixture
  5. filtrationwas filtered off through Celite
  6. washthe solution was washed with H2O (3×)
  7. dry with materialdried over Na2SO4
  8. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-547997e0125d4179924c62c7e732fb60
Source dataset
uspto-grants-2010_05
Patent number
US07723329B2

Reaction notes

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