Dimethylformamide → 7-Chlorothieno[3,2-b]pyridine-2-carboxamide
Reaktionsgleichung
[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[CH:8]=[C:9]([C:11]([O-:13])=O)[S:10][C:3]=12.[Li+].S(Cl)(Cl)=O.C(Cl)Cl.C[N:23](C=O)C>>[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[CH:8]=[C:9]([C:11]([NH2:23])=[O:13])[S:10][C:3]=12Komponenten
5
Versuchsvorschrift
A solution of lithium 7-chloro-thieno[3,2-b]pyridine-2-carboxylate (1.0 g, 4.7 mmol), thionyl chloride (7.0 mmol, 3.5 mL), CH2Cl2 (40 mL), and DMF (0.4 mL) was heated to reflux. After 3 h the resulting yellow solution was concentrated under reduced pressure, the resulting residue was suspended in CH2Cl2 (60 mL), and NH3 gas was bubbled through the mixture for 10 min. The reaction mixture was filtered to give the title compound as a white solid (1.17 g, 100%). MS: 213.0/215.1 (MH+); HPLC Rf: 3.44 min; HPLC purity: 98%.