Sodium Hydroxide → Aniline, p-(ethylsulfonyl)-

HRID 2268771Notes

Reaction equation

HRID 2268771 reaction equation
O.O.[Sn](Cl)Cl.[CH2:6]([S:8]([C:11]1[CH:16]=[CH:15][C:14]([N+:17]([O-])=O)=[CH:13][CH:12]=1)(=[O:10])=[O:9])[CH3:7].[OH-].[Na+]>C(O)C>[CH2:6]([S:8]([C:11]1[CH:16]=[CH:15][C:14]([NH2:17])=[CH:13][CH:12]=1)(=[O:10])=[O:9])[CH3:7]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 61436Stannous chloride dihydrateHCID 24591461-(ethylsulfonyl)-4-nitrobenzene

Product 1

HCID 22795Aniline, p-(ethylsulfonyl)-

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Tin (II) chloride dihydrate (51.89 g, 0.230 mol) was added to 1-(ethylsulfonyl)-4-nitrobenzene (10 g, 0.046 mol) in ethanol (250 ml) then heated under reflux for 16 h. The mixture was cooled to room temperature and treated with aqueous sodium hydroxide (2N, 100 ml). The product was then extracted into ethyl acetate (3×150 ml). The organic extracts were combined, dried (MgSO4) and concentrated in vacuo. The residue was then purified by chromatography column over silica (50% ethyl acetate/50% petroleum ether) to afford 4-(ethylsulfonyl)-benzene amine. δ(1H NMR, DMSO, ppm): 1.00 (3H, t), 2.95 (2H, q), 5.95 (2H, s), 6.55 (2H, d), 7.35(2H, d).

Workup

  1. temperaturethen heated
  2. temperatureunder reflux for 16 h
  3. extractionThe product was then extracted into ethyl acetate (3×150 ml)
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated in vacuo
  6. customThe residue was then purified by chromatography column over silica (50% ethyl acetate/50% petroleum ether)

Sources & evidence

ORD record
ord-726266faa32f49eca04cf8bf01b8a877
Source dataset
uspto-grants-2001_12
Patent number
US06329366B1

Reaction notes

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