Реакция #166279

Уравнение реакции

3-amino benzenesulfonic acid

4-tert-butyl benzoyl chloride

→

3-(4-tert-butylbenzamido)benzenesulfonic acid

Выход 63.0%

Растворители

pyridine

Условия реакции

Обработка

1. 1
   Другоеthe solvent was evaporated under vacuum
2. 2
   workup.DISSOLUTIONThe residue was dissolved in EtOAc
3. 3
   Промывкаwashed with 1 M aqueous hydrochloric acid
4. 4
   ЭкстракцияThe aqueous washes were extracted with EtOAc
5. 5
   СушкаThe combined organic extracts were dried over Na2SO4
6. 6
   Концентрированиеconcentrated under vacuum
7. 7
   ДругоеThe residue was purified by silica gel chromatography (10%-20% MeOH—CH2Cl2)

Методика

To a solution of 3-amino benzenesulfonic acid (1.7 g, 10 mmol) in pyridine (100 mL) was added 4-tert-butyl benzoyl chloride (2.0 mL, 10 mmol). The reaction was stirred at room temperature 16 h and the solvent was evaporated under vacuum. The residue was dissolved in EtOAc and washed with 1 M aqueous hydrochloric acid. The aqueous washes were extracted with EtOAc. The combined organic extracts were dried over Na2SO4 and concentrated under vacuum. The residue was purified by silica gel chromatography (10%-20% MeOH—CH2Cl2) to obtain 3-(4-tert-butylbenzamido)benzenesulfonic acid (2.1 g, 63% yield). LC/MS: m/z 334.3 (M+H)+ at 2.79 min (10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA)).

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