Реакция #3592

Уравнение реакции

water

ethyl 4-aminobenzoate

2-methylbenzoyl chloride

triethylamine

→

ethyl 4-[(2-methylbenzoyl)amino]benzoate

Выход 76.5%

Растворители

dichloromethane

Условия реакции

Обработка

1. 1
   Температураis cooled in an ice bath
2. 2
   workup.ADDITIONthe addition
3. 3
   Другоеthe organic layer separated
4. 4
   ПромывкаThe organic layer is washed with water, 1N HCl, 1M NaHCO3
5. 5
   Сушкаdried over Na2SO4
6. 6
   ДругоеThe solvent is removed
7. 7
   Фильтрацияthe solid slurried with ethyl acetate and filtered

Методика

A mixture of 43.42 g of ethyl 4-aminobenzoate and 40.8 g of 2-methylbenzoyl chloride in 150 ml of dichloromethane is cooled in an ice bath and 26.56 g of triethylamine the solution is stirrer the addition, the solution is stirred at room temperature overnight. The mixture is poured into water and the organic layer separated. The organic layer is washed with water, 1N HCl, 1M NaHCO3 and dried over Na2SO4. The solvent is removed and the solid slurried with ethyl acetate and filtered to give 57 g of ethyl 4-[(2-methylbenzoyl)amino]benzoate as crystals, m.p. 110°-115° C. A mixture of 50.7 g of the preceding compound in 280 ml of ethyl alcohol and 55 ml of 10N NaOH is refluxed for 5 minutes. The mixture is cooled to room temperature, diluted with 200 ml of water and acidified with concentrated hydrochloric acid (pH 1-2). The mixture is filtered and the solid washed with water and dried to give 51 g of the desired product as white crystals, m.p. 270°-275° C.

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