Реакция #2467990

Уравнение реакции

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

potassium carbonate

iodomethane

potassium iodide

→

product

Выход 57.3%

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

Выход 57.3%

Растворители

acetone

Условия реакции

Обработка

1. 1
   ФильтрацияThe solution was filtered
2. 2
   Промывкаthe solids were washed with acetone
3. 3
   ДругоеAcetone was evaporated under reduced pressure
4. 4
   workup.ADDITIONdiluted with ice cold water
5. 5
   workup.STIRRINGstirred for 10 min
6. 6
   ЭкстракцияThe solution was extracted with chloroform (4×75 mL)
7. 7
   Промывкаthe combined CHCl3 layer was washed with water, brine
8. 8
   Сушкаdried over sodium sulfate
9. 9
   ФильтрацияThe solution was filtered
10. 10
    Другоеevaporated the solvent
11. 11
    ДругоеThe residue was chromatographed over silica gel column

Методика

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.

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