Sulphenone → Hydrazine, (4-(phenylsulfonyl)phenyl)-

HRID 1815613Notes

Reaction equation

HRID 1815613 reaction equation
[C:1]1([S:7]([C:10]2[CH:15]=[CH:14][C:13](Cl)=[CH:12][CH:11]=2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.O.[NH2:18][NH2:19]>C(N(CC)CC)C.C(O)CO.O>[C:1]1([S:7]([C:10]2[CH:15]=[CH:14][C:13]([NH:18][NH2:19])=[CH:12][CH:11]=2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 2

HCID 6621SulphenoneHCID 24654Hydrazine hydrate (1:1)

Product 1

HCID 116834Hydrazine, (4-(phenylsulfonyl)phenyl)-

Reagents, catalysts & solvents 3

HCID 8471TriethylamineCatalystHCID 174Ethylene GlycolSolventHCID 962WaterSolvent

Procedure

A mixture of 4-chlorophenyl phenyl sulfone (10.1 g, 40.0 mmol), hydrazine mono hydrate (30 mL), and triethylamine (4 drops) in ethylene glycol (20 mL) is heated at 150° for 15 hr. Upon cooling, the mixture is diluted with H2O and filtered. The residual solid is washed with H2O until the washings are neural (pH=6). This material is then triturated with methylene chloride and dried under reduced pressure at 50° to give the title compound, IR (drift) 3282, 1586, 1514, 1306, 1291, 1158, 1145, 1104, 996, 813, 756, 730, 717, 688 and 678 cm−1, NMR (300 MHz, CDCl3) 7.70-7.85, 7.45-7.65, 6.79 and 4.22 δ; MS (EI) m/z 248 (M+), 125, 123, 108, 107, 90, 80, 77, 63 and 51.

Workup

  1. temperatureis heated at 150° for 15 hr
  2. temperatureUpon cooling
  3. filtrationfiltered
  4. washThe residual solid is washed with H2O until the washings
  5. customThis material is then triturated with methylene chloride
  6. customdried under reduced pressure at 50°

Sources & evidence

ORD record
ord-37bb6ed265094ab58fba3c1636883a80
Source dataset
uspto-grants-2005_04
Patent number
US06878823B2

Reaction notes

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