Ethanone, 1-[4-fluoro-2-(methylamino)phenyl]-2-(methylsulfinyl)- → 1-(4-Fluoro-2-methylaminophenyl)-2-(methylthio)ethanone

HRID 1089766Notes

Reaction equation

HRID 1089766 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:13])[CH2:9][S:10]([CH3:12])=O)=[C:4]([NH:14][CH3:15])[CH:3]=1.S([O-])(O)=O.[Na+]>O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:13])[CH2:9][S:10][CH3:12])=[C:4]([NH:14][CH3:15])[CH:3]=1

Participants

4

Reactant 2

HCID 10059700Ethanone, 1-[4-fluoro-2-(methylamino)phenyl]-2-(methylsulfinyl)-HCID 23665763Sodium Bisulfite

Product 1

HCID 199784741-(4-Fluoro-2-methylaminophenyl)-2-(methylthio)ethanone

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 1-(4-fluoro-2-methylaminophenyl)-2-methylsulphinylethanone (100 g), prepared in a similar manner to that described in Example 1, sodium hydrogen sulphite (1 kg) and water (2.5 1) was stirred under nitrogen and heated at 90°-105° for 3 hours. The mixture, was allowed to cool and then stood at ambient temperature for 72 hours. The mixture was extracted with dichloromethane (3×250 ml) and the combined extracts evaporated to give a solid product. Crystallisation from hexane gave 1-(4-fluoro-2-methylaminophenyl)-2-(methylthio)ethanone, m.p. 61.5°-63°.

Workup

  1. customprepared in a similar manner to that
  2. temperatureheated at 90°-105° for 3 hours
  3. temperatureto cool
  4. extractionThe mixture was extracted with dichloromethane (3×250 ml)
  5. customthe combined extracts evaporated
  6. customto give a solid product
  7. customCrystallisation from hexane

Sources & evidence

ORD record
ord-fbebcd8fb6b94d05baa7770ec53116d7
Source dataset
uspto-grants-1992_01
Patent number
US05079264

Reaction notes

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