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Thioanisole → 2-[5-(dimethoxymethyl)-4,5-dihydro-1,3-thiazol-2-yl]-5-(2-methoxyethoxy)-7-nitro-1H-indole

HRID 1960413
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1960413
C1(P(=O)(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.FC(F)(F)C(OC(=O)C(F)(F)F)=O.C([S:41][CH:42]([CH:64]([O:67][CH3:68])[O:65][CH3:66])[CH2:43][NH:44][C:45]([C:47]1[NH:48][C:49]2[C:54]([CH:55]=1)=[CH:53][C:52]([O:56][CH2:57][CH2:58][O:59][CH3:60])=[CH:51][C:50]=2[N+:61]([O-:63])=[O:62])=O)C1C=CC=CC=1.C1(SC)C=CC=CC=1>ClCCl.CCCCCC.C(OCC)(=O)C.O>[CH3:66][O:65][CH:64]([O:67][CH3:68])[CH:42]1[S:41][C:45]([C:47]2[NH:48][C:49]3[C:54]([CH:55]=2)=[CH:53][C:52]([O:56][CH2:57][CH2:58][O:59][CH3:60])=[CH:51][C:50]=3[N+:61]([O-:63])=[O:62])=[N:44][CH2:43]1
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Komponenten

9

Edukt 4

HCID 7520ThioanisoleHCID 9845Trifluoroacetic anhydrideHCID 13097Triphenylphosphine OxideHCID 59136022N-[2-(benzylthio)-3,3-dimethoxypropyl]-5-(2-methoxyethoxy)-7-nitro-1H-indole-2-carboxamide

Produkt 1

HCID 574762212-[5-(dimethoxymethyl)-4,5-dihydro-1,3-thiazol-2-yl]-5-(2-methoxyethoxy)-7-nitro-1H-indole
Ausbeute 173,2 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel2×HCID 8058HexaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

Triphenylphosphine oxide (3 g) was dissolved in dichloromethane (30 mL), trifluoroacetic anhydride (3.1 g) was added under ice-cooling, and the mixture was stirred for 10 min. A solution of N-[2-(benzylthio)-3,3-dimethoxypropyl]-5-(2-methoxyethoxy)-7-nitro-1H-indole-2-carboxamide (5.0 g) and thioanisole (2.5 g) in dichloromethane (20 mL) was added dropwise to this suspension under ice-cooling. The reaction solution was allowed to warm to room temperature, and stirred for 10 min. Water was added, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over magnesium sulfate, and filtrated, and the filtrate was concentrated under reduced pressure. The obtained crude product was subjected to silica gel column chromatography (ethyl acetate:hexane=10:90-40:60), and the obtained solid was washed with ethyl acetate-hexane to give the title compound (6.8 g, yield 97%) as yellow crystals. melting point 100-101° C.

Aufarbeitung

  1. temperaturecooling
  2. temperaturecooling
  3. stirringstirred for 10 min
  4. extractionthe mixture was extracted with ethyl acetate
  5. washThe organic layer was washed with saturated brine
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltrated
  8. concentrationthe filtrate was concentrated under reduced pressure
  9. customThe obtained crude product
  10. washthe obtained solid was washed with ethyl acetate-hexane

Quellen und Nachweise

ORD-Eintrag
ord-b36f7e5e1a584b1b8d51071d78645e4a
Quelldatensatz
uspto-grants-2013_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08410087B2

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