Réaction #2517

Équation de réaction

sodium bicarbonate

o-anisidine

4-nitrobenzoic acid

1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride

→

title compound

Rendement 87.5%

4-Nitro-N-(2-methoxyphenyl)benzamide

Rendement 87.5%

Solvants

methylene chloride

Conditions de réaction

Traitement

1. 1
   TempératureWith cooling in an ice bath
2. 2
   Extractionextracted with methylene chloride
3. 3
   Lavagewashed with water and saturated brine in that order
4. 4
   SéchageAfter drying on anhydrous magnesium sulfate
5. 5
   Autrethe solvent was removed by evaporation
6. 6
   Autrethe resulting solid material was purified by silica gel column chromatography (methylene chloride)

Mode opératoire

With cooling in an ice bath, 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDC.HCl) (630 mg, 3.29 mmol) was added to 15 ml of methylene chloride solution containing o-anisidine (368 mg, 2.99 mmol) and 4-nitrobenzoic acid (500 mg, 2.99 mmol). After 1 hour of stirring at the same temperature, the reaction mixture was roughly adjusted to pH 8 with saturated sodium bicarbonate aqueous solution, extracted with methylene chloride and then washed with water and saturated brine in that order. After drying on anhydrous magnesium sulfate, the solvent was removed by evaporation, and the resulting solid material was purified by silica gel column chromatography (methylene chloride) to obtain 712 mg (87.4%) of the title compound in the form of yellow powder.

Source