Reaktion #166279

Reaktionsgleichung

3-amino benzenesulfonic acid

4-tert-butyl benzoyl chloride

→

3-(4-tert-butylbenzamido)benzenesulfonic acid

Ausbeute 63.0%

Lösungsmittel

pyridine

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigethe solvent was evaporated under vacuum
2. 2
   workup.DISSOLUTIONThe residue was dissolved in EtOAc
3. 3
   Waschenwashed with 1 M aqueous hydrochloric acid
4. 4
   ExtraktionThe aqueous washes were extracted with EtOAc
5. 5
   TrocknenThe combined organic extracts were dried over Na2SO4
6. 6
   Einengenconcentrated under vacuum
7. 7
   SonstigeThe residue was purified by silica gel chromatography (10%-20% MeOH—CH2Cl2)

Vorschrift

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)).

Quelle