2-Mercaptobenzoic Acid → 2-[(3-Methoxyphenyl)sulfanyl]benzoic acid

Temperatur

165 °C

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).

1. customby sparging with nitrogen for 10 min
2. temperaturecooled
3. additionThe reaction mixture was poured onto a mixture of 500 g of ice plus 40 mL of concentrated HCl
4. customThe resulting precipitate was collected
5. washwashed with water
6. customdried
7. dissolutionThe precipitate was dissolved in acetone
8. filtrationfiltered through Celite
9. concentrationconcentrated
10. customThe product was purified by recrystallization from aqueous ethanol
11. customA tan powder was obtained

ORD-Eintrag

ord-0536f15731294b0d91a9b24a06ada3c7

Quelldatensatz

uspto-grants-2008_12

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07459263B2