Pyridine → HCID 11300023, compound

To 50 g (0.463 mole) of p-cresol (4-methylphenol) and 37 mL (0.458 mole) of pyridine dissolved in 250 mL of chloroform was added 50 g (0.226 mole) of 3-nitrobenzenesulfonyl chloride. The reaction was allowed to stir at ambient temperature. After 2 hours, the reaction was judged complete by TLC and the volatiles were removed by rotary evaporation. The resulting residue was treated with 400 mL of 0.5 M sodium bicarbonate. The insoluble product was collected and washed with sodium bicarbonate (2 times, 200 mL each) and water (2 times, 300 mL each). The solid was then treated with methanol (200 mL) followed by water (200 mL). The solid was collected by vacuum filtration and washed with water. This solid was treated with 170 g (0.897 mole) of tin (II) chloride dissolved in 250 mL of concentrated HCl. The reaction was allowed to stir at ambient temperature for 40 hours. TLC indicated that the reaction was incomplete, so the reaction was heated at 50 C for 27 hours. The solid precipitate was collected by vacuum filtration and was washed with 6N HCl. The solid was extracted with ethyl acetate and water. The ethyl acetate layer was washed with brine, dried with magnesium sulfate, filtered, and the volatiles removed by rotary evaporation to yield 42.5 g of compound 5 as an oil that solidified on standing.

1. customthe volatiles were removed by rotary evaporation
2. additionThe resulting residue was treated with 400 mL of 0.5 M sodium bicarbonate
3. customThe insoluble product was collected
4. washwashed with sodium bicarbonate (2 times, 200 mL each) and water (2 times, 300 mL each)
5. additionThe solid was then treated with methanol (200 mL)
6. filtrationThe solid was collected by vacuum filtration
7. washwashed with water
8. stirringto stir at ambient temperature for 40 hours
9. temperaturewas heated at 50 C for 27 hours
10. filtrationThe solid precipitate was collected by vacuum filtration
11. washwas washed with 6N HCl
12. extractionThe solid was extracted with ethyl acetate and water
13. washThe ethyl acetate layer was washed with brine
14. dry with materialdried with magnesium sulfate
15. filtrationfiltered
16. customthe volatiles removed by rotary evaporation

ORD record

ord-fc7c84b695ff493b9d788642c9763ea0

Source dataset

uspto-grants-2006_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07071231B2