Ethanol → Ethyl 3-chlorobenzimidate hydrochloride

To a solution of 3-chlorobenzonitrile (50 g, 363 mmol) in anhydrous ethanol (500 mL), cooled to 0° C. in an ice bath, was bubbled HCl (g) through a gas dispersion tube for approximately 20 minutes until the solution was saturated. The resulting reaction mixture was stirred at room temperature for 16 h. Volatiles were removed in vacuo and the residue was triturated with anhydrous ether (˜200 mL). The white solid was collected by filtration and dried in vacuo overnight to afford ethyl 3-chlorobenzimidate hydrochloride (INTERMEDIATE II.1) (80 g, 363 mmol, 100%) which was used directly without further purification.

1. customwas bubbled HCl (g) through a gas dispersion tube for approximately 20 minutes until the solution
2. customThe resulting reaction mixture
3. customVolatiles were removed in vacuo
4. customthe residue was triturated with anhydrous ether (˜200 mL)
5. filtrationThe white solid was collected by filtration
6. customdried in vacuo overnight

ORD record

ord-bb4e323615f34b59885f49acecccb010

Source dataset

uspto-grants-2010_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07820649B2