Dimethylamine → N,N-dimethyl-[6-[4-(2-thenoyl)benzoyl]-4,5,6,7-tetrahydrofuro[2,3-c]pyridin-2-ylmethyl]amine
Reaktionsgleichung
[C:1]1([C:6]([C:8]2[CH:24]=[CH:23][C:11]([C:12]([N:14]3[CH2:19][CH2:18][C:17]4[CH:20]=[CH:21][O:22][C:16]=4[CH2:15]3)=[O:13])=[CH:10][CH:9]=2)=[O:7])[S:5][CH:4]=[CH:3][CH:2]=1.[CH3:25][NH:26][CH3:27].[CH2:28]=O>C(O)(=O)C>[CH3:25][N:26]([CH2:28][C:21]1[O:22][C:16]2[CH2:15][N:14]([C:12](=[O:13])[C:11]3[CH:10]=[CH:9][C:8]([C:6](=[O:7])[C:1]4[S:5][CH:4]=[CH:3][CH:2]=4)=[CH:24][CH:23]=3)[CH2:19][CH2:18][C:17]=2[CH:20]=1)[CH3:27]Komponenten
5
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 100 °C
Versuchsvorschrift
To a solution of 0.251 g (0.744 mmol) of 6-[4-(2-thenoyl)benzoyl]-4,5,6,7-tetrahydrofuro[2,3-c]pyridine in 10 ml of acetic acid, 0.10 g (1.1 mmol) of 50% aqueous dimethylamine and 0.09 g (1.1 mmol) of 37% aqueous formaldehyde were added, followed by stirring at 100° C. for 0.5 hours. After the solvent was distilled off under reduced pressure, the residual solution was alkalified with an aqueous sodium hydroxide and extracted with ethyl acetate 3 times. The combined organic layer was dried over anhydrous magnesium sulfate; the solvent was distilled off under reduced pressure. The resulting crude product was purified by silica gel column chromatography (ethyl acetate to ethyl acetate/methanol=4/1) to yield the desired product.
Aufarbeitung
- distillationAfter the solvent was distilled off under reduced pressure
- extractionextracted with ethyl acetate 3 times
- dry with materialThe combined organic layer was dried over anhydrous magnesium sulfate
- distillationthe solvent was distilled off under reduced pressure
- customThe resulting crude product was purified by silica gel column chromatography (ethyl acetate to ethyl acetate/methanol=4/1)
Quellen und Nachweise
- ORD-Eintrag
- ord-5de31371bdc6443c855ede361b009347
- Quelldatensatz
- uspto-grants-1999_12
- Patentnummer
- US05998433
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