Hydrochloric Acid → 3-Fluorobenzene-1-carboximidamide--hydrogen chloride (1/1)

To a solution of hexamethyldisilazane (13.8 g, 85.6 mmol) in diethyl ether (143 ml) was added dropwise a 1.6 N solution (53.5 ml, 85.6 mmol) of n-butyllithium in hexane under ice-cooling. Thereto 3-fluorobenzonitrile (5.00 g, 41.3 mmol) was added, followed by stirring at room temperature for 2 hours. Thereto 3 N hydrochloric acid (57 ml) was added dropwiseunder ice-cooling, and the reaction mixture was stirred at room temperature for 0.5 hour. Water (200 ml) was added thereto, and the ether layer was removed. The aqueous layer was basified with an aqueous 3 N sodium hydroxide solution, and then extracted with chloroform. The extract was dried over anhydrous magnesium sulfate and the solvent was distilled off under reduced pressure. A 4 N solution (50 ml) of hydrogen chloride in ethyl acetate was added to the residue, and 4.65 g (64.5%) of the desired product as a solid was collected by filtration.

1. temperaturecooling
2. temperaturecooling
3. stirringthe reaction mixture was stirred at room temperature for 0.5 hour
4. customthe ether layer was removed
5. extractionextracted with chloroform
6. dry with materialThe extract was dried over anhydrous magnesium sulfate
7. distillationthe solvent was distilled off under reduced pressure
8. additionA 4 N solution (50 ml) of hydrogen chloride in ethyl acetate was added to the residue, and 4.65 g (64.5%) of the desired product as a solid
9. filtrationwas collected by filtration

ORD record

ord-333de7074b7f460c80fe48e085567070

Source dataset

uspto-grants-2010_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07851473B2