N-[2-(Phenylmethyl)phenyl]-2-chloroacetamide synthesis

Yield: 85%

Reaction Conditions:

with pyridine in toluene at 0 - 20; for 1.5 h;Inert atmosphere;

Steps:

N-(2-benzylphenyl)-2-chloroacetamide (12).
A samples of commercially available 2-benzylaniline (1841 mg, 10.05 mmol) in toluene (10 mL) at 0 °C under Ar was treated with chloroacetyl chloride (0.82 mL, 10.25 mmol) and pyridine (0.98 mL, 12.11 mmol). Reaction mixture was stirred at 0 °C for 30 min and at rt for 1 h, and the reaction was quenched with water (5 mL). Resulting mixture was stirred for 20 min, diluted with EtOAc (200 mL), washed with aqueous 1N HCl (3 x 30 mL) and saturated aqueous NaCl, dried over anhydrous MgSO₄ and concentrated under reduced pressure to provide compound 12 as a gray solid (2205 mg, 85%): ¹H NMR (CDCl₃, 400 MHz) δ 7.99 (br s, 1H), 7.84 (d, J = 8.0 Hz, 1H), 7.34-7.11 (m, 8H), 4.06 (s, 2H), 4.00 (s, 2H); CAS Registry: 21535-43-3.

References:

Park, Sang Won;Kang, Han Eol;Yun, Wheesahng;Lee, Sang Yeul;Nam, Tae-gyu [Tetrahedron Letters,2019,art. no. 151451] Location in patent:supporting information