Cl.[Cl:2][C:3]1[CH:10]=[CH:9][C:6]([C:7]#[N:8])=[CH:5][CH:4]=1.[CH2:11]([OH:13])[CH3:12]>>[ClH:2].[Cl:2][C:3]1[CH:10]=[CH:9][C:6]([C:7](=[NH:8])[O:13][CH2:11][CH3:12])=[CH:5][CH:4]=1Hydrogen chloride gas was passed through a solution of 4-chloro-benzonitrile (1.0 g, 7.3 mmol) in anhydrous ethanol (100 mL) cooled to 0° C. After 3 h, hydrogen chloride gas was stopped and the reaction mixture was stirred at room temperature for 16 h. The solvent was removed and the residue was triturated in diethyl ether to afford ethyl 4-chloro-benzimidate hydrochloride (1.12 g, 83%). It was used without further purification.
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