Thionyl Chloride → O-methyl (4'-methylbiphenyl-2-yl)carbonylthiocarbamate

In chloroform (40 ml) was dissolved (4'-methylbiphenyl-2-yl)carboxylic acid (10 g). To the solution was added thionyl chloride (7 ml), and the mixture was heated for 3 hours under reflux. The reaction mixture was poured into ice-water, then the organic layer was separated, washed with water and concentrated to dryness to give a syrup, which was dissolved in dioxane (80 ml). To the solution was added powdered potassium thiocyanate (9.16 g), and the mixture was heated for one hour under reflux. The reaction mixture was allowed to cool, and then insolubles were filtered off. After addition of methanol (15 ml) to the filtrate, the solution was heated for 15 minutes under reflux. The reaction solution was concentrated to dryness, and the resulting crystals were crystallized from isopropyl ether to afford the title compound as white plates (7.4 g, 55%),

1. temperaturethe mixture was heated for 3 hours
2. temperatureunder reflux
3. customthe organic layer was separated
4. washwashed with water
5. concentrationconcentrated to dryness
6. customto give a syrup, which
7. temperaturethe mixture was heated for one hour
8. temperatureunder reflux
9. temperatureto cool
10. filtrationinsolubles were filtered off
11. additionAfter addition of methanol (15 ml) to the filtrate
12. temperaturethe solution was heated for 15 minutes
13. temperatureunder reflux
14. concentrationThe reaction solution was concentrated to dryness
15. customthe resulting crystals were crystallized from isopropyl ether

ORD-Eintrag

ord-3530d84ddd434b9796c4ba61b9c55ed4

Quelldatensatz

uspto-grants-1993_09

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US05243054