Chloroform → 2-Propyloxybenzamidine Hydrochloride

21.41 g (400 mmol) of ammonium chloride are suspended in 400 ml of toluene and cooled to 0–5° C. 200 ml of a 2M solution of triethylaluminium in hexane are added dropwise, and the mixture is stirred at room temperature until the evolution of gas has ceased. After addition of 32.2 g (200 mmol) of 2-propoxybenzonitrile, the reaction mixture is stirred at 80° C. (bath) overnight. With ice-cooling, the cooled reaction mixture is added to a suspension of 300 g of silica gel and 2.85 1 of ice-cooled chloroform, and the mixture is stirred for 30 minutes. The mixture is filtered off with suction and the filter residue is washed with the same amount of methanol. The solvent is distilled off under reduced pressure, the residue is stirred with 500 ml of a mixture of dichloromethane and methanol (9:1), the solid is filtered off and the mother liquor is concentrated. The residue is stirred with petroleum ether and filtered off with suction. This gives 22.3 g (52%) of product.

1. temperaturecooled to 0–5° C
2. stirringthe reaction mixture is stirred at 80° C. (bath) overnight
3. temperatureWith ice-cooling
4. customthe cooled reaction mixture
5. additionis added to a suspension of 300 g of silica gel and 2.85 1 of ice-
6. stirringthe mixture is stirred for 30 minutes
7. filtrationThe mixture is filtered off with suction
8. washthe filter residue is washed with the same amount of methanol
9. distillationThe solvent is distilled off under reduced pressure
10. stirringthe residue is stirred with 500 ml of a mixture of dichloromethane and methanol (9:1)
11. filtrationthe solid is filtered off
12. concentrationthe mother liquor is concentrated
13. stirringThe residue is stirred with petroleum ether
14. filtrationfiltered off with suction

ORD record

ord-403739dbe43d4a4bb96862317c4b95ff

Source dataset

uspto-grants-2006_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07122540B2