Stannous Chloride → 2-(Cyclopentylsulfonyl)benzenamine

HRID 852240Notes

Reaction equation

HRID 852240 reaction equation
[CH:1]1([S:6]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[N+:15]([O-])=O)(=[O:8])=[O:7])[CH2:5][CH2:4][CH2:3][CH2:2]1.Cl[Sn]Cl>CCO>[CH:1]1([S:6]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[NH2:15])(=[O:8])=[O:7])[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 24479Stannous ChlorideHCID 12646358HCID 12646358, compound

Product 1

HCID 126463672-(Cyclopentylsulfonyl)benzenamineYield 66%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 1-cyclopentanesulfonyl-2-nitrobenzene (0.66 g, 2.6 mmol) and SnCl2 (2.4 g, 10.34 mmol) in EtOH (10 ml) was heated under reflux for 2 h. The solvent was removed under reduced pressure and the resulting crude was dissolved in AcOEt (100 ml) and washed with sodium hydroxide 2N (30 ml) and brine (10 ml). The organic layer was dried (MgSO4) and the solvents removed under reduced pressure to give the title compound (0.38 g, 66%) as a white solid.

Workup

  1. temperatureunder reflux for 2 h
  2. customThe solvent was removed under reduced pressure
  3. dissolutionthe resulting crude was dissolved in AcOEt (100 ml)
  4. washwashed with sodium hydroxide 2N (30 ml) and brine (10 ml)
  5. dry with materialThe organic layer was dried (MgSO4)
  6. customthe solvents removed under reduced pressure

Sources & evidence

ORD record
ord-bf0b343fd829486c9ffb9106c949fb81
Source dataset
uspto-grants-2007_08
Patent number
US07253171B2

Reaction notes

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