Benzonitrile, 4-bromo- → 4-Bromobenzene-1-carboximidamide--hydrogen chloride (1/1)

Temperature

25 °C

Sodium methoxide (0.81 g, 15 mmol) was dissolved in methanol (150 mL) and 4-bromobenzonitrile (27.3 g, 150 mmol) was added and the mixture was stirred at 25° C. for 24 h. Solid ammonium chloride (8.1 g, 150 mmol) was added and the mixture was stirred for an additional 24 h. The mixture was filtered, the solid was washed with methanol and ether, and the filtrate was combined and concentrated. The white residue was collected and washed thoroughly with ether and dried under vacuum to give 4-bromobenzenecarboximidamide hydrochloride (16 g, 54%) as a white solid. HRMS: calcd for C7H7BrN2+H+, 198.98654; found (ESI, [M+H]+), 198.9868; Analytical HPLC: purity 98.4% at 246 nm, 3.4 min; 97.8% at 210-370 nm, 3.4 min; the Xterra® RP18 column, 3.5μ, 150×4.6 mm column, 1.2 mL/min, 85/15-5/95 (Ammon. Form. Buff. pH=3.5/ACN+MeOH) for 10 min, hold 4 min.

1. stirringthe mixture was stirred for an additional 24 h
2. filtrationThe mixture was filtered
3. washthe solid was washed with methanol and ether
4. concentrationconcentrated
5. customThe white residue was collected
6. washwashed thoroughly with ether
7. customdried under vacuum

ORD record

ord-64b1267486264c8283500d01821bdc3b

Source dataset

uspto-grants-2009_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07618990B2