Sodium Chloride → HCID 178510797, compound

Participants

Reaction Conditions

Reaction Steps

The crude 2-phenyl-acetamidine hydrochloride (1.32 g, 7.74 mmol) was dissolved in water (10 mL) and cooled to 0° C. A ˜1.7 M solution of sodium hypochlorite in water (3.68 mL, 6.26 mmol) was added dropwise. The reaction mixture was stirred 1 h, then solid sodium chloride was added to saturate the aqueous phase, which was extracted with ethyl acetate (2×25 mL). The combined organic phases were filtered through sodium sulfate and evaporated in vacuo. The residue was purified by flash column chromatography (Merck silica gel 60, 40-63 μm; 33% ethyl acetate/hexanes) to afford N-chloro-2-phenyl-acetamidine (155 mg, 9% over two steps) as an off-white semi-solid: H1-NMR (400 MHz, CDCl3) δ=3.67 (2H, s), 5.13 (2H, br), 7.31 (5H, m).

Provenance & Evidence