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Triphenylphosphine Oxide → N-[2-(4,5-dihydro-1,3-thiazol-2-yl)-4-methyl-1H-indol-7-yl]thiophene-2-sulfonamide

HRID 1851477
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1851477
C1(P(=O)(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.FC(F)(F)S(OS(C(F)(F)F)(=O)=O)(=O)=O.[CH3:36][C:37]1[CH:45]=[CH:44][C:43]([NH:46][S:47]([C:50]2[S:51][CH:52]=[CH:53][CH:54]=2)(=[O:49])=[O:48])=[C:42]2[C:38]=1[CH:39]=[C:40]([C:55]([NH:57][CH2:58][CH2:59][S:60]C(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)=O)[NH:41]2.C(=O)([O-])O.[Na+]>ClCCl>[S:60]1[CH2:59][CH2:58][N:57]=[C:55]1[C:40]1[NH:41][C:42]2[C:38]([CH:39]=1)=[C:37]([CH3:36])[CH:45]=[CH:44][C:43]=2[NH:46][S:47]([C:50]1[S:51][CH:52]=[CH:53][CH:54]=1)(=[O:49])=[O:48]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 13097Triphenylphosphine OxideHCID 67749Trifluoromethanesulfonic anhydrideHCID 516892Sodium BicarbonateHCID 579016404-Methyl-7-[(2-thienylsulfonyl)amino]-N-[2-(tritylthio)ethyl]-1H-indole-2-carboxamide

Produkt 1

HCID 57901806N-[2-(4,5-dihydro-1,3-thiazol-2-yl)-4-methyl-1H-indol-7-yl]thiophene-2-sulfonamide
Ausbeute 91 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A mixture of triphenylphosphine oxide (2.1 g), trifluoromethanesulfonic anhydride (0.63 mL) and dichloromethane (35 mL) was stirred for 30 min under ice-cooling. 4-Methyl-7-[(2-thienylsulfonyl)amino]-N-[2-(tritylthio)ethyl]-1H-indole-2-carboxamide (0.80 g) was added, and the mixture was stirred for 90 min under ice-cooling. The reaction mixture was poured into aqueous sodium hydrogencarbonate solution and extracted with dichloromethane. The aqueous layer was extracted with dichloromethane, and the combined dichloromethane layer was dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography (ethyl acetate:hexane=3:7-5:5), and the obtained crystals were recrystallized from ethyl acetate-hexane to give the title compound (431 mg, yield 91%) as colorless prism crystals. melting point 198-199° C.

Aufarbeitung

  1. temperaturecooling
  2. stirringthe mixture was stirred for 90 min under ice-
  3. temperaturecooling
  4. extractionextracted with dichloromethane
  5. extractionThe aqueous layer was extracted with dichloromethane
  6. dry with materialthe combined dichloromethane layer was dried over anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customthe obtained crystals were recrystallized from ethyl acetate-hexane

Quellen und Nachweise

ORD-Eintrag
ord-ac44e460f3b6489eb7fad33ab8e7ca8f
Quelldatensatz
uspto-grants-2015_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08957070B2

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