Ammonium Chloride → 4-Methylbenzene-1-carboximidamide hydrochloride

To a solution of p-methylbenzimidate hydrochloride (8.00 g, 43.09 mmol) in MeCH (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 removed 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 preciptate is filtered. The beige filtrate is concentrated to yield p-methylbenzamidine hydrochloride as an off-white solid (7.15 g, 97%).

1. temperaturecooled in refrigerator
2. customthe precipitate is removed by filtration
3. concentrationThe mother liquor is concentrated
4. customto yield the crude product which
5. filtrationthe white preciptate is filtered
6. concentrationThe beige filtrate is concentrated

ORD record

ord-e4dc2ce7f8e849fb82c3fa4c3162e5e0

Source dataset

uspto-grants-2000_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06156776