Reaction #2467990

Reaction equation

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

potassium carbonate

iodomethane

potassium iodide

→

product

Yield 57.3%

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

Yield 57.3%

Solvents

acetone

Conditions

Workup

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

Procedure

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.

Source