Ammonium Hydroxide → HCID 15058685, compound

A mixture of 1.3 gram (0.0054 mole) of 2,3-di(2-fluoroethoxy)benzoic acid, 1.0 gram (0.0080 mole) of oxalyl chloride, and one drop of N,N-dimethylformamide in 20 ml of diethyl ether was stirred at room temperature for approximately 18 hours. The solvent was evaporated from the reaction mixture leaving a residue. This residue was dissolved in 100 ml of methylene chloride, and the resulting organic solution was added slowly to a stirred, cold (0° C.) aqueous solution of ammonium hydroxide (5 ml of 30% solution). This mixture was allowed to warm to room temperature and stir for approximately 18 hours. The mixture was washed with an aqueous, sodium bicarbonate solution followed by an aqueous, saturated sodium chloride solution. The washed organic phase was dried over anhydrous magnesium sulfate and filtered. The filtrate was evaporated under reduced pressure leaving a solid residue. Recrystallization of this solid from a mixture of toluene and n-hexane yielded 0.6 gram of 2,3-di(2-fluoroethoxy)benzamide, mp 100°-101° C.

1. customThe solvent was evaporated from the reaction mixture
2. customleaving a residue
3. temperatureto warm to room temperature
4. stirringstir for approximately 18 hours
5. washThe mixture was washed with an aqueous, sodium bicarbonate solution
6. dry with materialThe washed organic phase was dried over anhydrous magnesium sulfate
7. filtrationfiltered
8. customThe filtrate was evaporated under reduced pressure
9. customleaving a solid residue
10. customRecrystallization of this solid
11. additionfrom a mixture of toluene and n-hexane

ORD record

ord-55c65ef56b1147df9f8292a37d4086fe

Source dataset

uspto-grants-1990_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04960884