Reaction #502134

Reaction equation

methanol

ammonium chloride

trimethylaluminium

3,4-dichlorophenylacetonitrile

→

title compound

2-(3,4-Dichlorophenyl)ethanamidine hydrochloride

Solvents

toluene

toluene

Conditions

Workup

1. 1
   Temperaturethe mixture is warmed to room temperature
2. 2
   workup.STIRRINGthe mixture is stirred at 80° C. overnight
3. 3
   TemperatureAfter cooling to 0° C.
4. 4
   OtherThe product is separated from the precipitated solid by filtration with suction
5. 5
   Washthe filter cake is washed several times with methanol
6. 6
   OtherThe combined filtrates are evaporated to dryness
7. 7
   Filtrationagain filtered with suction

Procedure

2.88 g (54 mmol) of ammonium chloride are suspended in 50 ml of toluene under an argon atmosphere and cooled to 0° C. After dropwise addition of 27 ml of a 2 M trimethylaluminium solution in toluene, the mixture is warmed to room temperature and then stirred for 1.5 h. 5 g (27 mmol) of 3,4-dichlorophenylacetonitrile are added, and the mixture is stirred at 80° C. overnight. After cooling to 0° C., 50 ml of methanol are added dropwise. The product is separated from the precipitated solid by filtration with suction, and the filter cake is washed several times with methanol. The combined filtrates are evaporated to dryness, and the residue is then suspended in dichloromethane/methanol 10:1 and again filtered with suction. Concentration of the filtrate results in 6.2 g (77% of theory) of the title compound.

Source