| 44% |
|
Example 2.3; Preparation of 4-Furan-2-yl-6-thiophen-2-yl-2-thioxo-l,2-dihydro- pyridine-3-carbonitrileAll fumes from this reaction were vented through a bleach trap:A steady stream of oxygen was bubbled through a solution of (E)-3-furan-2-yl-l-thiophen-2- yl-propenone (1.0 g, 4.90 mmol) and 2-cyano-thioacetamide (540 mg, 5.39 mmol) in DMSO (14 mL). The mixture was cooled to O0C before portionwise addition of potassium tert- butoxide (1.65 g, 14.7 mmol) over 15 min. The reaction was warmed to 5O0C and stirred vigorously, still bubbling O2 through. On completion, the reaction was cooled to room temperature and slowly transferred into 4M HCl (65 mL) cooled in an ice bath (N.B. liberation of HCN) - keeping the temperature below 2O0C. This solution was stirred until the evolution of gas ceased (approx. Vz hr) and filtered, washing the precipitate with water and ethanol. The precipitate was triturated with ether and filtered. The precipitate was triturated with hot glacial acetic acid and filtered on cooling to give pure product (617 mg, 44% yield), as a mixture of monomer and dimer, as an orange solid.1H nmr (300 MHz, CDCl3) delta 7.70, s, IH, Ar-H; 7.58, m, 1eta, Ar-H; 7.52, dd, 2eta, / 1.2, 3.9 Hz, Ar-H; 7.24, dd, 1eta, / 1.2, 5.1 Hz, Ar-H; 6.91, dd, 1eta, J 3.6, 5.1 Hz, Ar-H; 6.55, dd, 1eta, J 1.8, 3.6 Hz, Ar-H.MS (ESI+) m/z 567 (M+l) (dimer) |
| 44% |
With potassium tert-butylate; In dimethyl sulfoxide; at 0 - 50℃; for 0.25h; |
2.3: Preparation of 4-Furan-2-yl-6-thiophen-2-yl-2-thioxo-l,2-dihydro-pyridine-3- carbonitrile; All fumes from this reaction were vented through a bleach trap:A steady stream of oxygen was bubbled through a solution of (E)-3-furan-2-yl-l-thiophen-2- yl-propenone (1.0 g, 4.90 mmol) and 2-cyano-thioacetamide (540 mg, 5.39 mmol) in DMSO (14 mL). The mixture was cooled to O0C before portionwise addition of potassium tert- butoxide (1.65 g, 14.7 mmol) over 15 minutes. The reaction was warmed to 5O0C and stirred vigorously, still bubbling O2 through. On completion, the reaction was cooled to room temperature and slowly transferred into 4M HCl (65 mL) cooled in an ice bath (N.B. liberation of HCN) - keeping the temperature below 2O0C. This solution was stirred until the evolution of gas ceased (approx. Vz hr) and filtered, washing the precipitate with water and <n="30"/>ethanol. The precipitate was triturated with ether and filtered. The precipitate was triturated with hot glacial acetic acid and filtered on cooling to give pure product (617 mg, 44% yield), as a mixture of monomer and dimer, as an orange solid.1H NMR (CDCl3) delta 7.70, s, IH, Ar-H; 7.58, m, IH, Ar-H; 7.52, dd, 2eta, J 1.2, 3.9 Hz, Ar-H; 7.24, dd, 1eta, J 1.2, 5.1 Hz, Ar-H; 6.91, dd, 1eta, 73.6, 5.1 Hz, Ar-H; 6.55, dd, 1eta, J 1.8, 3.6 Hz, Ar-H.MS (ESI+) m/z 567 (dimer M+l) |
| 44% |
|
Example 2.3 Preparation of 4-Furan-2-yI-6-thiophen-2-yl-2-thioxo-l,2-dihydro- pyridine-3-carbonitriIeAU fumes from this reaction were vented through a bleach trap:A steady stream of oxygen was bubbled through a solution of (E)-3-furan-2-yl-l-thiophen-2- yl-propenone (1.0 g, 4.90 mmol) and 2-cyano-thioacetamide (540 mg, 5.39 mmol) in DMSO (14 mL). The mixture was cooled to O0C before portionwise addition of potassium tert- butoxide (1.65 g, 14.7 mmol) over 15 minutes. The reaction was warmed to 5O0C and stirred vigorously, still bubbling O2 through. On completion, the reaction was cooled to room temperature and slowly transferred into 4M HCl (65 mL) cooled in an ice bath (N.B. liberation of HCN) - keeping the temperature below 2O0C. This solution was stirred until the evolution of gas ceased (approx. Vi hr) and filtered, washing the precipitate with water and ethanol. The precipitate was triturated with ether and filtered. The precipitate was triturated with hot glacial acetic acid and filtered on cooling to give pure product (617 mg, 44%), as a mixture of monomer and dimer, as an orange solid.1H NMR delta (300 MHz, CDCl3) delta 7.70, s, IH, Ar-H; 7.58, m, 1eta, Ar-H; 7.52, dd, 2eta, / 1.2, 3.9 Hz, Ar-H; 7.24, dd, 1eta, / 1.2, 5.1 Hz, Ar-H; 6.91, dd, 1eta, J 3.6, 5.1 Hz, Ar-H; 6.55, dd, 1eta, / 1.8, 3.6 Hz, Ar-H.MS (ESI+) m/z 567 (dimer M+l) |
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