Triethylamine → HCID 18691205, compound

To a mixture of 8.2 g of 2-methyl-3-(2-thienyl)acrylic acid and 9.5 ml of triethylamine in 45 ml of acetone was added dropwise 7.2 ml of ethyl chlorocarbonate over a period of 30 minutes under ice-cooling with stirring. After being stirred for 1 hour, a solution of 5.1 g of sodium azide in 10 ml of water was added dropwise over 30 minutes, and then stirred for 1 hour. The reaction mixture was poured into water and extracted with benzene. The extract was washed with water and saturated saline, and dried over anhydrous magnesium sulfate. Drying agent was removed by filtration, and the solvent was removed under reduced pressure, and then 15 ml of diphenylether was added to the residue. The resultant solution was added dropwise to a mixture of 14 ml of tri-n-butylamine and 35 ml of diphenylether at 200° C. When addition was complete, the reaction mixture was allowed to cool and the crystalline precipitate was washed with diethyl ether to give 6.2 g of 6-methylthieno[3,2-c]pyridin-4(5H)-one as a pale yellow powder.

1. temperaturecooling
2. stirringAfter being stirred for 1 hour
3. stirringstirred for 1 hour
4. extractionextracted with benzene
5. washThe extract was washed with water and saturated saline
6. dry with materialdried over anhydrous magnesium sulfate
7. customDrying agent
8. customwas removed by filtration
9. customthe solvent was removed under reduced pressure
10. addition15 ml of diphenylether was added to the residue
11. additionThe resultant solution was added dropwise to a mixture of 14 ml of tri-n-butylamine and 35 ml of diphenylether at 200° C
12. additionWhen addition
13. temperatureto cool
14. washthe crystalline precipitate was washed with diethyl ether

ORD record

ord-41a55a64ec8b4d638b575423ad9d3aa8

Source dataset

uspto-grants-2000_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06020342