Reaktion #2467990

Reaktionsgleichung

3H-thiopheno[2,3-d]1,2,3-triazin-4-one

potassium carbonate

iodomethane

potassium iodide

→

product

Ausbeute 57.3%

3-Methylthiopheno[2,3-d]1,2,3-triazin-4-one

Ausbeute 57.3%

Lösungsmittel

acetone

Reaktionsbedingungen

Aufarbeitung

1. 1
   FiltrationThe solution was filtered
2. 2
   Waschenthe solids were washed with acetone
3. 3
   SonstigeAcetone was evaporated under reduced pressure
4. 4
   workup.ADDITIONdiluted with ice cold water
5. 5
   workup.STIRRINGstirred for 10 min
6. 6
   ExtraktionThe solution was extracted with chloroform (4×75 mL)
7. 7
   Waschenthe combined CHCl3 layer was washed with water, brine
8. 8
   Trocknendried over sodium sulfate
9. 9
   FiltrationThe solution was filtered
10. 10
    Sonstigeevaporated the solvent
11. 11
    SonstigeThe residue was chromatographed over silica gel column

Vorschrift

To a solution of 3H-thiopheno[2,3-d]1,2,3-triazin-4-one (80 mg, 0.522 mmol) in acetone (50 mL) was added sequentially potassium carbonate (144 mg, 1.04 mmol), iodomethane (0.04 mL, 0.627 mmol) and potassium iodide (catalytic) at rt and the mixture was stirred at rt for 3 h. The solution was filtered and the solids were washed with acetone. Acetone was evaporated under reduced pressure, diluted with ice cold water and stirred for 10 min. The solution was extracted with chloroform (4×75 mL) and the combined CHCl3 layer was washed with water, brine and dried over sodium sulfate. The solution was filtered and evaporated the solvent. The residue was chromatographed over silica gel column using hexane-ethyl acetate (90:10) as eluents to give the product as an off-white solid (50 mg, 57%), mp 104-108° C. 1H NMR (400 MHz, DMSO-d6): δ 8.17 (1H, d, J=5.6 Hz), 7.64 (1H, d, J=5.6 Hz), 3.95 (3H, s); 13C NMR (100 MHz, CDCl3): δ 159.4, 153.9, 130.7, 125.6, 121.7, 37.3.

Quelle