m-Chloroperbenzoic acid → Ethanone, 1-[4-fluoro-2-(methylamino)phenyl]-2-(methylsulfinyl)-

HRID 1089787Notes

Reaction equation

HRID 1089787 reaction equation
ClC1C=C(C=CC=1)C(OO)=[O:6].[F:12][C:13]1[CH:18]=[CH:17][C:16]([C:19](=[O:23])[CH2:20][S:21][CH3:22])=[C:15]([NH:24][CH3:25])[CH:14]=1>ClCCl>[F:12][C:13]1[CH:18]=[CH:17][C:16]([C:19](=[O:23])[CH2:20][S:21]([CH3:22])=[O:6])=[C:15]([NH:24][CH3:25])[CH:14]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 199784741-(4-Fluoro-2-methylaminophenyl)-2-(methylthio)ethanone

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 3-chloroperoxybenzoic acid (3.49 g) in dichloromethane (80 ml) was added to a stirred solution of 1-(4-fluoro-2-methylaminophenyl)-2-(methylthio)ethanone (4.3 g), prepared in a similar manner to that described in Example 2, in dichloromethane (75 ml) under nitrogen over 15 minutes whilst maintaining the temperature below 25°. The mixture was stirred for a further 2 hours at ambient temperature. The solution was washed with saturated aqueous sodium hydrogen carbonate solution (3×50 ml) and evaporated in vacuo to give a solid product. Crystallisation from toluene gave 1-(4-fluoro-2-methylaminophenyl)-2-methylsulphinylethanone, m.p. 137°-138°.

Workup

  1. customprepared in a similar manner to that
  2. temperaturewhilst maintaining the temperature below 25°
  3. washThe solution was washed with saturated aqueous sodium hydrogen carbonate solution (3×50 ml)
  4. customevaporated in vacuo
  5. customto give a solid product
  6. customCrystallisation from toluene

Sources & evidence

ORD record
ord-38fdd755e4344e539ef42e8d5798479f
Source dataset
uspto-grants-1992_01
Patent number
US05079264

Reaction notes

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