N-Benzyl-2-Methoxy-N-MethylbenzaMide, 97% synthesis
- Product Name:N-Benzyl-2-Methoxy-N-MethylbenzaMide, 97%
- CAS Number:64302-58-5
- Molecular formula:C16H17NO2
- Molecular Weight:255.31
Yield:64302-58-5 51 %
Reaction Conditions:
Stage #1: N-benzyl-N-chloromethylamine;ortho-anisaldehydewith vanadyl sulfate trihydrate in ethyl acetate at 20;Inert atmosphere;Irradiation;
Stage #2: with triethylamine in ethyl acetate at 20;
Steps:
2.3. General procedure to compounds 3a-3u, 4a-4n
General procedure: In a round bottom flask of 25 mL, aldehyde (4 mmol) andVOSO43H2O (8.69 mg, 5% mol) were added to a solution of a N-chloroamine(0.8 mmol) in 1 mL AcOEt under Ar atmosphere and at roomtemperature. The mixture was stirred under blue led irradiation for 24 hunder Ar (the reaction was monitored by TLC until disappearance ofN-Cl-amine). Then was added NEt3 (0.8 mmol, 0.11 mL) and the reactionmixture left to stir at room temperature for 2 h until disappearanceof the intermediate acyl chloride (monitored by TLC). Then, the reactionmixture was quenched with water and extracted with AcOEt. The combined organic layers were washed three times with a solution of 5%citric acid and then three times with a solution of 5% NaHCO3; theorganic phase was dried over anhydrous Na2SO4, and the solvent wasevaporated under reduced pressure. The crude products were purifiedby flash chromatography on silica gel.
References:
Gaspa, Silvia;Sciortino, Giuseppe;Porcheddu, Andrea;Dell'Osa, Chiara;Satta, Giuseppe;Azzena, Ugo;Pisano, Luisa;Carraro, Massimo;Sanna, Daniele;Garribba, Eugenio;Maseras, Feliu;De Luca, Lidia [Molecular catalysis,2023,vol. 541,art. no. 113054]
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