Sodium Hydroxide → 3-(Methanesulfonylmethyl)aniline

HRID 514694Notes

Reaction equation

HRID 514694 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+]>Cl.C1COCC1.[Cl-].[Ti+3].[Cl-].[Cl-]>[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

6

Reactant 2

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

Product 1

HCID 219563393-(Methanesulfonylmethyl)anilineYield 102.1%

Reagents, catalysts & solvents 3

HCID 10313229titanium(III) trichlorideCatalystHCID 313Hydrochloric AcidSolventHCID 8028TetrahydrofuranSolvent

Procedure

Titanium(III)chloride solution (about 15%) in about 10% hydrochloric acid (162 mL; Merck Schuchardt OHG) was added to a stirred solution of 1-[(methylsulfonyl)methyl]-3-nitrobenzene (5.1 g; 23.8 mmol) in THF (250 mL) at room temperature and the batch was stirred for 16 hours. By adding 1N sodium hydroxide solution the pH value of the reaction mixture was raised to 10 before the batch was extracted with ethyl acetate (2×). The combined organic phases were washed with brine, filtered using a Whatman filter and concentrated to give the desired product (4.5 g) that was used without further purification.

Workup

  1. temperaturewas raised to 10 before the batch
  2. extractionwas extracted with ethyl acetate (2×)
  3. washThe combined organic phases were washed with brine
  4. filtrationfiltered
  5. filtrationfilter
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-55a767625104494a81a623826cd4e827
Source dataset
uspto-grants-2015_08
Patent number
US09108926B2

Reaction notes

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