Réaction #1447095

Équation de réaction

Phosphorus oxychloride

tin(IV) chloride

N-(4-bromo-3-methoxy-phenyl)-acetamide

4-ethylbenzoic acid

→

N-[4-Bromo-2-(4-ethyl-benzoyl)-5-methoxy-phenyl]-acetamide

Solvants

dichloromethane

1,2-dichloroethane

Conditions de réaction

Traitement

1. 1
   Autremaintains below 35° C
2. 2
   TempératureThe resulting mixture is heated
3. 3
   Températureat reflux temperature overnight
4. 4
   workup.ADDITIONpoured
5. 5
   Autreonto crushed ice
6. 6
   Autrethe organic phase is separated
7. 7
   Lavagewashed with 10% NaOH in water and water
8. 8
   SéchageThe organic phase is dried (sodium sulphate)
9. 9
   Autrethe solvent is removed
10. 10
    Autrethe residue is triturated with methanol
11. 11
    Autreto give the product

Mode opératoire

Phosphorus oxychloride (17 mL) and tin(IV) chloride (5 mL) are successively added to a suspension of N-(4-bromo-3-methoxy-phenyl)-acetamide (5.0 g) and 4-ethylbenzoic acid (4.4 g) in 1,2-dichloroethane at such a rate that the temperature maintains below 35° C. The resulting mixture is heated at reflux temperature overnight. Then, the mixture is diluted with dichloromethane and poured onto crushed ice. After stirring the aqueous mixture for 30 min, the organic phase is separated and washed with 10% NaOH in water and water. The organic phase is dried (sodium sulphate), the solvent is removed and the residue is triturated with methanol to give the product.

Source