Toluene → HCID 68488483, compound

Temperature

80 °C

To a solution of 3-(ethylthio)acrylic acid (5.67 g) in toluene (50 mL) were added thionyl chloride (3.48 mL) and DMF (catalytic amount) at room temperature, and the mixture was stirred at 80° C. for 2 hours. The reaction mixture was concentrated under reduced pressure. To the residue was added acetonitrile (50 mL), and then was added dropwise a solution of aniline (8.78 g) in acetonitrile (10 mL) under ice-cooling. The mixture was stirred at the same temperature for 1 hour and then at room temperature for 3 hours, and then concentrated under reduced pressure. To the residue was added 1N hydrochloric acid (50 mL), and the mixture was stirred at room temperature for 0.5 hour. The formed crystals were collected by filtration, washed with water, filtered, and then dried to obtain 3-(ethylthio)-N-(phenyl)acrylamide (8.03 g) as a white crystal.

1. concentrationThe reaction mixture was concentrated under reduced pressure
2. additionTo the residue was added acetonitrile (50 mL)
3. additionwas added dropwise a solution of aniline (8.78 g) in acetonitrile (10 mL) under ice-
4. temperaturecooling
5. stirringThe mixture was stirred at the same temperature for 1 hour
6. waitat room temperature for 3 hours
7. concentrationconcentrated under reduced pressure
8. additionTo the residue was added 1N hydrochloric acid (50 mL)
9. stirringthe mixture was stirred at room temperature for 0.5 hour
10. filtrationThe formed crystals were collected by filtration
11. washwashed with water
12. filtrationfiltered
13. customdried

ORD record

ord-2b0313f0c60a460c963ff168c376144b

Source dataset

uspto-grants-2012_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08318981B2