2-chloro-N-(2-chloro-6-Methylphenyl)acetaMide synthesis

Yield:6307-67-1 98%

Reaction Conditions:

Stage #1: 2-chloro-6-methylanilinewith pyridine in dichloromethane at -10; for 0.166667 h;
Stage #2: chloroacetyl chloride in dichloromethane at -10 - 20; for 2 h;

Steps:

2.A A.

To a solution of 2-chloro-6-methyl-aniline (28) (25.0 g, 176.6 mmol) in CH₂Cl₂ (200 mL) was added pyridine (28.6 mL, 353 mmol) at -10° C. After 10 mins, chloroacetyl chloride (3a) (21.1 mL, 265 mmol) was added. The reaction mixture was allowed to warm to room temperature over a period of 2 h. A solution of 1 N HCl (500 mL) was added and the mixture was stirred for 10 mins. The organic phase was separated and the aqueous layer was extracted with CH₂Cl₂ (2×300 mL). The combined organic extracts were washed with 1 N HCl solution (400 mL), H₂O (400 mL) and brine (400 mL). It was dried over MgSO₄, filtered and concentrated in vacuo to give the product 29a as a white solid (37.8 g, 98% yield). ¹H NMR (500 MHz, CDCl₃) δ 2.28 (s, 3H), 4.25 (s, 2H), 7.14-7.18 (m, 2H), 7.26-7.31 (m, 1H), 8.02 (bs, 1H).

References:

US2007/219370,2007,A1 Location in patent:Page/Page column 27; 28