Reacción #2460298

Ecuación de reacción

thiosalicylic acid

3-iodoanisole

potassium carbonate

→

2-(3-methoxyphenylthio)benzoic acid

Disolventes

N-methylpyrrolidinone

Condiciones de reacción

Tratamiento posterior

1. 1
   Otroby sparging with nitrogen for 10 min
2. 2
   Temperaturacooled
3. 3
   workup.ADDITIONThe reaction mixture was poured onto a mixture of 500 g of ice plus 40 mL of concentrated HCl
4. 4
   OtroThe resulting precipitate was collected
5. 5
   Lavadowashed with water
6. 6
   Otrodried
7. 7
   workup.DISSOLUTIONThe precipitate was dissolved in acetone
8. 8
   Filtraciónfiltered through Celite
9. 9
   Concentraciónconcentrated
10. 10
    OtroThe product was purified by recrystallization from aqueous ethanol
11. 11
    OtroA tan powder was obtained

Procedimiento

First, 2-(3-methoxyphenylthio)benzoic acid was prepared. A stirred mixture of thiosalicylic acid (3.57 g, 23 mmol), 3-iodoanisole (5.42 g, 23 mmol), potassium carbonate (7.04 g, 51 mmol), copper powder (0.29 g, 5 mmol), and N-methylpyrrolidinone (75 mL) was deaerated by sparging with nitrogen for 10 min, heated at 165° C. for 2 h, and then cooled to ambient. The reaction mixture was poured onto a mixture of 500 g of ice plus 40 mL of concentrated HCl. The resulting precipitate was collected, washed with water, and dried. The precipitate was dissolved in acetone and filtered through Celite, then concentrated to deposit a crude product. The product was purified by recrystallization from aqueous ethanol. A tan powder was obtained, mass: 4.60 g (76% of theory).

Fuente