Reaktion #11357

Reaktionsgleichung

ammonium chloride

5-Benzyloxy-2-ethoxybenzonitrile

Trimethylaluminum

hexane

→

3-Benzyloxy-6-ethloxybenzamidine hydrochloride

Lösungsmittel

toluene

dichloromethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturthe mixture is cooled to 0–5° C
2. 2
   workup.STIRRINGthe mixture is stirred at 80° C. overnight
3. 3
   SonstigeThe cooled reaction mixture
4. 4
   Temperaturcooling
5. 5
   workup.STIRRINGthe mixture is stirred for 30 min
6. 6
   FiltrationThe mixture is filtered off with suction
7. 7
   Waschenthe filter cake is washed with methanol
8. 8
   Einengenconcentrated
9. 9
   SonstigeThe resulting residue is triturated
10. 10
    workup.ADDITIONa mixture of dicloromethane/methanol 9:1
11. 11
    Filtrationfiltered
12. 12
    Einengenconcentrated
13. 13
    Sonstigea rotary evaporator
14. 14
    SonstigeThe residue is then triturated with ether
15. 15
    Filtrationthe colorless solid is filtered off with suction

Vorschrift

46.46 g of ammonium chloride (868.5 mol) are suspended in 650 ml of toluene, and the mixture is cooled to 0–5° C. Trimethylaluminum is added dropwise as a 2M solution in hexane (445 ml, 888.3 mmol), and the mixture is then stirred at room temperature until the evolution of gas has ceased. 5-Benzyloxy-2-ethoxybenzonitrile (100 g, 394.8 mmol) (example 32A) is added, and the mixture is stirred at 80° C. overnight. The cooled reaction mixture is with ice-cooling, added to a suspension of 200 g of silica gel and 2 l of dichloromethane, and the mixture is stirred for 30 min. The mixture is filtered off with suction and the filter cake is washed with methanol. The organic phases are combined and concentrated. The resulting residue is triturated using a mixture of dicloromethane/methanol 9:1, filtered and concentrated using a rotary evaporator. The residue is then triturated with ether, and the colorless solid is filtered off with suction.

Quelle