Methanol → HCID 86648961, Verbindung

HRID 449921Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 449921
[Cl:1][C:2]1[CH:22]=[C:21]([CH:23]=C)[CH:20]=[C:19]([Cl:25])[C:3]=1[C:4]([NH:6][C:7]1[CH:12]=[CH:11][N:10]=[C:9]([NH:13][C:14]([CH:16]2[CH2:18][CH2:17]2)=[O:15])[CH:8]=1)=[O:5].C[OH:27]>C(Cl)Cl>[Cl:25][C:19]1[CH:20]=[C:21]([CH:23]=[O:27])[CH:22]=[C:2]([Cl:1])[C:3]=1[C:4]([NH:6][C:7]1[CH:12]=[CH:11][N:10]=[C:9]([NH:13][C:14]([CH:16]2[CH2:17][CH2:18]2)=[O:15])[CH:8]=1)=[O:5]

Komponenten

4

Edukt 2

HCID 887MethanolHCID 671286562,6-dichloro-N-(2-(cyclopropanecarboxamido)pyridin-4-yl)-4-vinylbenzamide

Produkt 1

HCID 86648961HCID 86648961, VerbindungAusbeute 86 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

2,6-dichloro-N-(2-(cyclopropanecarboxamido)pyridin-4-yl)-4-vinylbenzamide (750 mg, 1.99 mmol) was dissolved in a solution of MeOH (14 mL) and DCM (28 mL). The resulting mixture was cooled to −78° C., O3 was bubbled into the solution for 7 min, N2 was bubbled for 10 min, and then Me2S (14 mL) was added. The reaction mixture was slowly warmed to room temperature and stirred for 20 min. The mixture was concentrated under reduced pressure to provide 2,6-dichloro-N-(2-(cyclopropanecarboxamido)pyridin-4-yl)-4-formylbenzamide (0.70 g, yield: 86%). LCMS (ESI) m/z: 378.1 [M+H+].

Aufarbeitung

  1. customO3 was bubbled into the solution for 7 min
  2. customN2 was bubbled for 10 min
  3. additionMe2S (14 mL) was added
  4. temperatureThe reaction mixture was slowly warmed to room temperature
  5. concentrationThe mixture was concentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-0aff287a4b6d4fa2a0cca6e23d01d417
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08486950B2

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