4-Toluenesulfonyl chloride → 2-(Toluene-4-sulfonylamino)-benzoic acid methyl ester

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Reaction Steps

To a mixture of 2-Amino-benzoic acid methyl ester (900 g, 6 mol) in pyridine (6 L) was added p-Toluenesulfonyl chloride (1500 g, 7.5 mol). The mixture was stirred overnight at room temperature. The mixture was poured into ice water, and the resultant precipitates were collected by filtration. The filtrates were dissolved in CH2Cl2, and the solution washed with diluted HCl, H2O, and dried over MgSO4. The residue thus obtained was crystallized from ethanol to give 2-(Toluene-4-sulfonylamino)-benzoic acid methyl ester (1454 g, 80%).

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