Tetrahydrofuran → 2-(3-Chloropyridin-4-yl)-5-(trifluoromethylthio)benzoxazole

HRID 884889Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 884889
[Cl:1][C:2]1[CH:22]=[N:21][CH:20]=[CH:19][C:3]=1[C:4]([NH:6][C:7]1[CH:12]=[C:11]([S:13][C:14]([F:17])([F:16])[F:15])[CH:10]=[CH:9][C:8]=1[OH:18])=O.O1CCCC1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:22]=[N:21][CH:20]=[CH:19][C:3]=1[C:4]1[O:18][C:8]2[CH:9]=[CH:10][C:11]([S:13][C:14]([F:17])([F:16])[F:15])=[CH:12][C:7]=2[N:6]=1

Komponenten

6

Edukt 4

HCID 8028TetrahydrofuranHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 66881883HCID 66881883, Verbindung

Produkt 1

HCID 668809412-(3-Chloropyridin-4-yl)-5-(trifluoromethylthio)benzoxazoleAusbeute 93,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

To a mixture of 0.64 g of 3-chloro-N-[2-hydroxy-5-(trifluoromethylthio)phenyl]isonicotinamide, 6 ml of tetrahydrofuran and 0.53 g of triphenylphosphine, 0.87 g of 40% toluene solution of diethyl azodicarboxylate was added dropwise at room temperature and stirred for 1.5 hours. The reaction mixture was concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to give 0.57 g of 2-(3-chloropyridin-4-yl)-5-(trifluoromethylthio)benzoxazole (hereinafter, referred to as “active compound 77”).

Aufarbeitung

  1. additionwas added dropwise at room temperature
  2. concentrationThe reaction mixture was concentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-51149e08da8048a5b7a40d32eba51bec
Quelldatensatz
uspto-grants-2012_08
Patentnummer
US08242133B2

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