Acetyl chloride → ethyl N-acetyl-o-chlorobenzimidate

Reaktionsgleichung

[Cl:1][C:2]1[CH:12]=[CH:11][CH:10]=[CH:9][C:3]=1[C:4](=[NH:8])[O:5][CH2:6][CH3:7].C(N(CC)CC)C.[C:20](Cl)(=[O:22])[CH3:21]>C(Cl)Cl>[C:20]([N:8]=[C:4]([O:5][CH2:6][CH3:7])[C:3]1[CH:9]=[CH:10][CH:11]=[CH:12][C:2]=1[Cl:1])(=[O:22])[CH3:21]

Komponenten

Versuchsvorschrift

A mixture of 41 g (22.3 mmol) of ethyl o-chlorobenzimidate and 25 g (25 mmol) of triethylamine in 500 ml of methylene chloride is treated dropwise with 19.5 g (24.8 mmol) of acetyl chloride, the temperature being held at 40° C. by the use of cooling. The reaction mixture is stirred at room temperature for a further 30 minutes, and the mixture is then washed in sequence with water, 5% sodium bicarbonate solution and semi-saturated sodium chloride solution, dried over anhydrous magnesium sulfate and evaporated under reduced pressure. After distillation of the crude product at 110° C./0.16 mmHg (21.33 Pa) there is obtained ethyl N-acetyl-o-chlorobenzimidate as a colourless liquid.