2-Chloro-N-(2-isopropyl-phenyl)-acetamide synthesis

Yield:57503-03-4 94%

Reaction Conditions:

with sodium hydrogencarbonate in ethyl acetate at 20; for 1.66667 h;Cooling with ice;

Steps:

2.1 Step 1. 2-Chloro-N-(2-isopropylphenyl)acetamide (C₉)

Step 1.
2-Chloro-N-(2-isopropylphenyl)acetamide (C₉)
To a stirred solution of 2-isopropylaniline (3.0 g, 22.19 mmol) in ethyl acetate (22 mL) cooled in an ice bath were added sequentially sodium bicarbonate (3.73 g, 44.4 mmol) and chloroacetyl chloride (2.1 mL, 26.6 mmol) dropwise over four minutes.
After stirring in the ice bath for ten minutes, the reaction mixture was warmed to room temperature and stirred for 90 minutes.
Water (15 mL) was added to the reaction mixture, and the phases were separated.
The organic layer was washed with brine (20 mL), dried over magnesium sulfate, filtered, and concentrated to afford the title compound as a dark solid (4.9 g, 94%): ¹H NMR (400 MHz, CDCl₃) δ 8.32 (s, 1H), 7.82-7.75 (m, 1H), 7.35-7.29 (m, 1H), 7.25-7.21 (m, 2H), 4.26 (s, 2H), 3.04 (hept, J=6.9 Hz, 1H), 1.28 (d, J=6.8 Hz, 6H); ¹³C NMR (126 MHz, CDCl₃) δ 164.06, 140.06, 133.10, 126.57, 126.50, 125.77, 123.78, 43.21, 28.12, 22.87; IR (thin film) 3255, 2963, 2869, 1662, 1525 cm-1.

References:

US2018/99958,2018,A1 Location in patent:Paragraph 0247-0249