2-Methanesulfonylamino-benzoic acid methyl ester synthesis

Yield:716-41-6 98%

Reaction Conditions:

with pyridine at 0 - 25; for 3 h;Inert atmosphere;

Steps:

9 5.9. Methyl 2-(methylsulfonamido)benzoate (11)

5.9
Methyl 2-(methylsulfonamido)benzoate (11)
To a stirred solution of methyl 2-aminobenzoate (25.0 g, 165.6 mmol) in pyridine (200 mL) at 0 °C, methane sulfonyl chloride (13 mL, 168 mmol) was added drop wise and the mixture stirred at 25 °C for 3 h.
After completion, the reaction was quenched with ice cold water and extracted with ethyl acetate (3 * 200 mL).
The organic layer was washed with water (50 mL), brine (50 mL), dried with anhydrous sodium sulfate and concentrated.
The resulting crude product eluted at ethyl acetate in hexane (1/4 by volume).
The fractions with product were concentrated to obtain methyl 2-(methylsulfonamido)benzoate as white solid (37.0 g, yield: 98%).

References:

Lei, Kang;Hua, Xue-Wen;Tao, Yuan-Yuan;Liu, Yang;Liu, Na;Ma, Yi;Li, Yong-Hong;Xu, Xiao-Hua;Kong, Chui-Hua [Bioorganic and Medicinal Chemistry,2016,vol. 24,# 2,p. 92 - 103] Location in patent:supporting information