Sodium Hydroxide → HCID 58980636, compound

HRID 735792Notes

Reaction equation

HRID 735792 reaction equation
O.O.[Sn](Cl)Cl.[C:6]([C:10]1[CH:15]=[CH:14][C:13]([S:16]([CH3:19])(=[O:18])=[O:17])=[C:12]([N+:20]([O-])=O)[CH:11]=1)([CH3:9])([CH3:8])[CH3:7].[OH-].[Na+]>C(OCC)(=O)C>[C:6]([C:10]1[CH:15]=[CH:14][C:13]([S:16]([CH3:19])(=[O:17])=[O:18])=[C:12]([NH2:20])[CH:11]=1)([CH3:9])([CH3:7])[CH3:8]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 61436Stannous chloride dihydrateHCID 58980656HCID 58980656, compound

Product 1

HCID 58980636HCID 58980636, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Tin(II) chloride dihydrate (2.73 g, 12.1 mmol) was added to a solution of the above sulfone (777 mg, 3.02 mmol) in ethyl acetate (15 mL). The mixture was heated to reflux for 0.5 h then cooled to room temperature and poured onto aqueous 2.0 M NaOH. The aqueous phase was extracted with diethyl ether and the combined organic layers were washed with saturated aqueous NaHCO3, dried over sodium sulfate, filtered and concentrated in vacuo to provide pure 5-tert-butyl-2-methanesulfonyl-phenylamine (618 mg, 90%) as a white solid.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 0.5 h
  3. extractionThe aqueous phase was extracted with diethyl ether
  4. washthe combined organic layers were washed with saturated aqueous NaHCO3
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-8dacfbdb554f4c78b531e9af3c1d2a1e
Source dataset
uspto-grants-2009_09
Patent number
US07592332B2

Reaction notes

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