Trifluoroacetic anhydride → HCID 57901755, Verbindung

HRID 1851346Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1851346
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[S:6]([NH:9][C:10]1[CH:11]=[CH:12][CH:13]=[C:14]2[C:18]=1[NH:17][C:16]([C:19]([NH2:21])=O)=[CH:15]2)(=[O:8])=[O:7].FC(F)(F)C(OC(=O)C(F)(F)F)=O>N1C=CC=CC=1>[C:19]([C:16]1[NH:17][C:18]2[C:14]([CH:15]=1)=[CH:13][CH:12]=[CH:11][C:10]=2[NH:9][S:6]([C:2]1[S:1][CH:5]=[CH:4][CH:3]=1)(=[O:7])=[O:8])#[N:21]

Komponenten

4

Edukt 2

HCID 9845Trifluoroacetic anhydrideHCID 57476167HCID 57476167, Verbindung

Produkt 1

HCID 57901755HCID 57901755, VerbindungAusbeute 92 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Versuchsvorschrift

To a mixture of 7-[(2-thienylsulfonyl)amino]-1H-indole-2-carboxamide (4.65 g) and pyridine (20 mL) was slowly added trifluoroacetic anhydride (4.50 mL) at 0° C., and the mixture was stirred for 1 hr. The reaction mixture was concentrated, 10% aqueous citric acid solution was added, and the resulting crystals were filtrated, washed with water and dried. The obtained crystals were subjected to silica gel column chromatography, and eluted with tetrahydrofuran-hexane (2:3, volume ratio). The eluate was treated with activated carbon and concentrated to give the title compound (4.04 g, yield 92%) as pale-yellow crystals. The crystals were recrystallized from ethyl acetate-hexane. melting point 283-284° C.

Aufarbeitung

  1. customat 0° C.
  2. concentrationThe reaction mixture was concentrated
  3. addition10% aqueous citric acid solution was added
  4. filtrationthe resulting crystals were filtrated
  5. washwashed with water
  6. customdried
  7. washeluted with tetrahydrofuran-hexane (2:3, volume ratio)
  8. additionThe eluate was treated with activated carbon
  9. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-cda5f657b65a4009acf0d2644afd8497
Quelldatensatz
uspto-grants-2015_02
Patentnummer
US08957070B2

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