m-Chloroperbenzoic acid → methyl 8-(1-(3,5-difluorophenylamino)ethyl)-2-(ethylsulfinyl)-4-oxo-4H-chromene-6-carboxylate

HRID 1947374Notes

Reaction equation

HRID 1947374 reaction equation
ClC1C=C(C=CC=1)C(OO)=[O:6].[F:12][C:13]1[CH:14]=[C:15]([NH:20][CH:21]([C:23]2[CH:24]=[C:25]([C:37]([O:39][CH3:40])=[O:38])[CH:26]=[C:27]3[C:32]=2[O:31][C:30]([S:33][CH2:34][CH3:35])=[CH:29][C:28]3=[O:36])[CH3:22])[CH:16]=[C:17]([F:19])[CH:18]=1>C(Cl)Cl>[F:12][C:13]1[CH:14]=[C:15]([NH:20][CH:21]([C:23]2[CH:24]=[C:25]([C:37]([O:39][CH3:40])=[O:38])[CH:26]=[C:27]3[C:32]=2[O:31][C:30]([S:33]([CH2:34][CH3:35])=[O:6])=[CH:29][C:28]3=[O:36])[CH3:22])[CH:16]=[C:17]([F:19])[CH:18]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 58235050HCID 58235050, compound

Product 1

HCID 58235048methyl 8-(1-(3,5-difluorophenylamino)ethyl)-2-(ethylsulfinyl)-4-oxo-4H-chromene-6-carboxylateYield 101.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-chlorobenzoperoxoic acid (326 mg, 1.13 mmol) was added in one portion to a stirred suspension of methyl 8-(1-(3,5-difluorophenylamino)ethyl)-2-(ethylthio)-4-oxo-4H-chromene-6-carboxylate (475 mg, 1.13 mmol) in DCM (5 mL) cooled with an water/ice bath. The resulting mixture was stirred at RT for 1 h. The suspension was cooled to −15° C. and filtered, the solid was washed with cold DCM (5 mL). The filtrate was then washed with an aq. sol. of sodium thiosulfate pentahydrate in water (10 mL), and with a mixture of a sat. sol. of NaHCO3 and water (1:1, 15 mL). The organic layer was decanted, dried over MgSO4 and evaporated to afford the crude product methyl 8-(1-(3,5-difluorophenylamino)ethyl)-2-(ethylsulfinyl)-4-oxo-4H-chromene-6-carboxylate (500 mg, 100%) as a reddish foam. Mass Spectrum: M+H+ 436.

Workup

  1. temperaturecooled with an water/ice bath
  2. temperatureThe suspension was cooled to −15° C.
  3. filtrationfiltered
  4. washthe solid was washed with cold DCM (5 mL)
  5. washThe filtrate was then washed with an aq. sol. of sodium thiosulfate pentahydrate in water (10 mL)
  6. additionwith a mixture of a sat. sol. of NaHCO3 and water (1:1, 15 mL)
  7. customThe organic layer was decanted
  8. dry with materialdried over MgSO4
  9. customevaporated

Sources & evidence

ORD record
ord-fe19a520281547108670e0d01a53f161
Source dataset
uspto-grants-2013_03
Patent number
US08399460B2

Reaction notes

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