Acetic Acid → HCID 9890141, Verbindung

HRID 1637201Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1637201
OO.[OH2:3].[C:4]1([S:10][C:11]2[C:12]3[CH:24]=[CH:23][C:22]([O:25][CH2:26][C:27]4[CH:28]=[N:29][CH:30]=[CH:31][CH:32]=4)=[CH:21][C:13]=3[S:14][C:15]=2[C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.C(O)(=[O:35])C>>[C:4]1([S:10]([C:11]2[C:12]3[CH:24]=[CH:23][C:22]([O:25][CH2:26][C:27]4[CH:28]=[N:29][CH:30]=[CH:31][CH:32]=4)=[CH:21][C:13]=3[S:14][C:15]=2[C:16]([O:18][CH2:19][CH3:20])=[O:17])(=[O:35])=[O:3])[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Komponenten

5

Edukt 4

HCID 176Acetic AcidHCID 784Hydrogen PeroxideHCID 962WaterHCID 9931973HCID 9931973, Verbindung

Produkt 1

HCID 9890141HCID 9890141, Verbindung

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

Hydrogen peroxide in water (0.42 ml of 30% w/v, 3.75 mmol) was added to a solution of ethyl 3-(phenylsulfanyl)-6-(3-pyridylmethoxy)benzo[b]thiophene-2-carboxylate (Example 1, 633 mg, 1.5 mmol) in acetic acid (4.5 ml). The mixture was heated to 100° C. for 90 minutes. The solvents were removed by evaporation under reduced pressure, and the residue was partitioned between ethyl acetate and aqueous sodium bicarbonate solution. The organic layer was separated, dried (magnesium sulfate) and concentrated under vacuo, and the residue flash chromatographed on silica gel using 1% methanol in dichloromethane as eluant. The less polar product was isolated and crystallised from dichloromethane and diethyl ether to give the title compound as a colourless solid (230 mg).

Aufarbeitung

  1. customThe solvents were removed by evaporation under reduced pressure
  2. customthe residue was partitioned between ethyl acetate and aqueous sodium bicarbonate solution
  3. customThe organic layer was separated
  4. dry with materialdried (magnesium sulfate)
  5. concentrationconcentrated under vacuo
  6. customthe residue flash chromatographed on silica gel using 1% methanol in dichloromethane as eluant
  7. customThe less polar product was isolated
  8. customcrystallised from dichloromethane and diethyl ether

Quellen und Nachweise

ORD-Eintrag
ord-d084c8ecde014ad2a7f8a5439727b9e4
Quelldatensatz
uspto-grants-2000_03
Patentnummer
US06040309

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