Hydrochloric Acid → HCID 18423073, compound

To a solution of 4-fluoro-2-methoxyaniline (3.0 g) in orthoxylene (50 ml) was added bis(2-chloroethyl)amine hydrochloride (3.8 g) and the mixture was refluxed under heating for 13 hr. The reaction mixture was poured into water and washed with isopropyl ether. To the aqueous layer was added an aqueous sodium hydroxide solution to make it alkaline (pH 12) and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine and dried over anhydrous magnesium sulfate and the solvent was evaporated to give a black oil. The oil was dissolved in methanol and conc. hydrochloric acid was added and the mixture was concentrated. To this concentrated solution added tetrahydrofuran to give the title compound (3.1 g) as pale-purple crystals.

1. temperaturethe mixture was refluxed
2. temperatureunder heating for 13 hr
3. washwashed with isopropyl ether
4. additionTo the aqueous layer was added an aqueous sodium hydroxide solution
5. extractionthe mixture was extracted with ethyl acetate
6. washThe extract was washed with saturated brine
7. dry with materialdried over anhydrous magnesium sulfate
8. customthe solvent was evaporated
9. customto give a black oil
10. concentrationthe mixture was concentrated
11. additionTo this concentrated solution added tetrahydrofuran

ORD record

ord-bf8516f7609346e7af9c7ee86dcffa31

Source dataset

uspto-grants-2002_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06455528B1