Sodium Hydroxide → 3-(Methanesulfonylmethyl)aniline

HRID 1633950Notes

Reaction equation

HRID 1633950 reaction equation
[CH3:1][S:2]([CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([N+:12]([O-])=O)[CH:7]=1)(=[O:4])=[O:3].[OH-].[Na+]>C(O)C>[CH3:1][S:2]([CH2:5][C:6]1[CH:7]=[C:8]([CH:9]=[CH:10][CH:11]=1)[NH2:12])(=[O:3])=[O:4]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 179084331-(Methanesulfonylmethyl)-3-nitrobenzene

Product 1

HCID 219563393-(Methanesulfonylmethyl)anilineYield 55.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1-Methylsulfonylmethyl-3-nitrobenzene (4.70 g, 21.8 mmol) was added ethanol (70 mL) and the mixture was heated to reflux. At reflux the mixture was added SnCl2 dihydrate (24.6 g, 109 mmol) and heating at reflux was continued for 1 hour. After cooling, the mixture was poured into ice/water (200 mL) and neutralised (to pH 7) with 1 N sodium hydroxide. The mixture was filtered through celite, and the filter cake was washed with ethyl acetate. The phases from the combined filtrate and washings were separated, and the aqueous phase was extracted with ethyl acetate (2×150 mL). The combined organic phases were dried (MgSO4) and evaporated in vacuo to afford 2.23 g (55%) 3-(methylsulfonylmethyl)aniline.

Workup

  1. temperaturethe mixture was heated to reflux
  2. temperatureAt reflux the mixture
  3. temperatureheating
  4. temperatureat reflux
  5. temperatureAfter cooling
  6. filtrationThe mixture was filtered through celite
  7. washthe filter cake was washed with ethyl acetate
  8. customThe phases from the combined filtrate and washings were separated
  9. extractionthe aqueous phase was extracted with ethyl acetate (2×150 mL)
  10. dry with materialThe combined organic phases were dried (MgSO4)
  11. customevaporated in vacuo

Sources & evidence

ORD record
ord-419d725560d445c3b988c21c79631844
Source dataset
uspto-grants-2003_01
Patent number
US06503949B1

Reaction notes

Loading…