Methanol → 2-(4-Methylphenyl)ethanimidamide hydrochloride

Temperature

0 °C

10.8 g (201 mmol) of ammonium chloride are suspended under argon in 200 ml of dry toluene and the suspension is cooled to 0° C. 100 ml of a 2M solution of trimethylaluminium in hexane are added dropwise and the mixture is stirred at room temperature until the evolution of gas is complete. After addition of 13.2 g (100 mmol) of 4-methylbenzyl cyanide, the reaction mixture is stirred overnight at 80° C. (bath). The cooled reaction mixture is treated with 35 ml of methanol and then stirred at room temperature for a further 1 h. The solid is then first filtered off with suction, and the filter cake is washed several times with methanol. The filtrate is concentrated, resuspended in dichloromethane/methanol 10/1, and the insoluble solid is filtered off. The solvent is then again evacuated from the filtrate in vacuo.

1. stirringthe reaction mixture is stirred overnight at 80° C. (bath)
2. customThe cooled reaction mixture
3. stirringstirred at room temperature for a further 1 h
4. filtrationThe solid is then first filtered off with suction
5. washthe filter cake is washed several times with methanol
6. concentrationThe filtrate is concentrated
7. filtrationthe insoluble solid is filtered off
8. customThe solvent is then again evacuated from the filtrate in vacuo

ORD record

ord-d05f8f7e152945bf97dd4c37702f04e2

Source dataset

uspto-grants-2003_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06573263B2