Ethanol → 4-Methylbenzene-1-carboximidamide hydrochloride

Participants

Reaction Steps

To a solution of p-methylbenzimidate hydrochloride (8.00 g, 43.09 mmol) in MeOH (100 ml) is added NH3/MeOH solution (2.68M, 24.12 ml, 64.64 mmol). Upon the addition of the NH3, the mixture has a pH around 8.5. To this solution is added ammonium chloride (2.30 g, 43.09 mmol). The reaction mixture is stirred at room temperature for 20 hours, then cooled in refrigerator and the precipitate is remoiva by filtration. The mother liquor is concentrated to yield the crude product which is taken up in a limited amount of cold EtOH and the white precipitate is filtered. The beige filtrate is concentrated to yield p-methylbenzamidine hydrochloride as an off-white solid (7.15 g, 97%). 1H NMR (DMSOd6): δ 2.41 (s, 3H), 7.43 (d, 2H), 7.78 (d, 2H), 9.24-9.39 (broad d, 3H).

Provenance & Evidence