Water → Methyl 4-[4-(4-fluorophenyl)-1,1-dioxoisothiazolidin-2-yl]-5-methanesulfonyl-2-methylbenzoate

HRID 501251Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 501251
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:12][S:11](=[O:14])(=[O:13])[NH:10][CH2:9]2)=[CH:4][CH:3]=1.F[C:16]1[C:25]([S:26]([CH3:29])(=[O:28])=[O:27])=[CH:24][C:19]([C:20]([O:22][CH3:23])=[O:21])=[C:18]([CH3:30])[CH:17]=1.C([O-])([O-])=O.[Cs+].[Cs+].O>CN(C=O)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]2[CH2:12][S:11](=[O:14])(=[O:13])[N:10]([C:16]3[C:25]([S:26]([CH3:29])(=[O:28])=[O:27])=[CH:24][C:19]([C:20]([O:22][CH3:23])=[O:21])=[C:18]([CH3:30])[CH:17]=3)[CH2:9]2)=[CH:6][CH:7]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 10796Cesium carbonateHCID 10538364Methyl 4-fluoro-5-methanesulfonyl-2-methylbenzoate2×HCID 684636364-(4-Fluorophenyl)-1,2-thiazolidine-1,1-dione

Produkt 1

HCID 68462085Methyl 4-[4-(4-fluorophenyl)-1,1-dioxoisothiazolidin-2-yl]-5-methanesulfonyl-2-methylbenzoateAusbeute 94,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

18.00 g of 4-(4-fluorophenyl)isothiazolidine 1,1-dioxide, 20.59 g of methyl 4-fluoro-5-methanesulfonyl-2-methylbenzoate (Journal of Medicinal Chemistry (1997), 40(13), 2017) and 81.75 g of Cs2CO3 were stirred in 500 ml of anhydrous DMF at RT for 5 hours. Then a further 2.00 g of methyl 4-fluoro-5-methanesulfonyl-2-methylbenzoate were added, and the mixture was stirred at RT for 1 hour and left to stand at RT for 15 hours. The reaction mixture was poured into 1800 ml of water and stirred at RT for 1 hour, and the product was filtered off with suction. The product was then dissolved in 1 l of EA, and the solution was mixed with MgSO4 and activated carbon and stirred at RT for 15 minutes. It was then filtered and the solvent was removed in vacuo. 35.00 g of a colorless foam were obtained.

Aufarbeitung

  1. waitleft
  2. waitto stand at RT for 15 hours
  3. stirringstirred at RT for 1 hour
  4. filtrationthe product was filtered off with suction
  5. dissolutionThe product was then dissolved in 1 l of EA
  6. additionthe solution was mixed with MgSO4 and activated carbon
  7. stirringstirred at RT for 15 minutes
  8. filtrationIt was then filtered
  9. customthe solvent was removed in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-828a5a89407b409191281d8af3dbcdd4
Quelldatensatz
uspto-grants-2010_08
Patentnummer
US07772262B2

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