Dimethylformamide → HCID 68602527, Verbindung

To a solution (60 ml) of 2-chloro-4-fluoro-3-methylbenzoic acid (5.66 g) synthesized by a known method in THF were added thionyl chloride (10.7 g) and DMF (0.2 ml) with stirring under ice-cooling, and the mixture was stirred at 70° C. for 3 hr. The solvent was evaporated under reduced pressure, and the residue was dissolved in dry THF (50 ml) and added dropwise to a mixture of concentrated aqueous ammonia (130 ml) and THF (86 ml) with stirring under ice-cooling. The mixture was stirred at the same temperature for 1 hr and extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the precipitated crystals were collected by filtration, washed with diethyl ether and dried to give 2-chloro-4-fluoro-3-methylbenzamide (4.82 g) as crystals.

1. temperaturecooling
2. stirringthe mixture was stirred at 70° C. for 3 hr
3. customThe solvent was evaporated under reduced pressure
4. dissolutionthe residue was dissolved in dry THF (50 ml)
5. additionadded dropwise to a mixture of concentrated aqueous ammonia (130 ml) and THF (86 ml)
6. stirringwith stirring under ice-
7. temperaturecooling
8. stirringThe mixture was stirred at the same temperature for 1 hr
9. extractionextracted with ethyl acetate
10. washThe organic layer was washed with saturated brine
11. dry with materialdried over anhydrous sodium sulfate
12. customThe solvent was evaporated under reduced pressure
13. filtrationthe precipitated crystals were collected by filtration
14. washwashed with diethyl ether
15. customdried

ORD-Eintrag

ord-e38a1ade01174ca0b3fa44a5ebdba199

Quelldatensatz

uspto-grants-2013_11

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08592452B2