Hydrochloric Acid → HCID 12282158, compound

Reaction equation

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]=1

Participants

Reactant 3

HCID 313Hydrochloric Acid2×

HCID 702Ethanol

HCID 121634-Chlorobenzonitrile

Product 1

HCID 12282158HCID 12282158, compoundYield 83%

Conditions

Temperature: 0 °C

Procedure

Hydrogen 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.