ChemicalBook CAS DataBase List 4,N-DIMETHYL-N-METHOXYBENZAMIDE

4,N-DIMETHYL-N-METHOXYBENZAMIDE synthesis

13synthesis methods

Product Name:4,N-DIMETHYL-N-METHOXYBENZAMIDE
CAS Number:122334-36-5
Molecular formula:C10H13NO2
Molecular Weight:179.22

99-94-5 Synthesis

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Yield: 98%

Reaction Conditions:

Stage #1:p-Toluic acid;N,0-dimethylhydroxylamine in toluene at 0; for 0.166667 h;
Stage #2: with phosphorus trichloride in toluene at 20 - 60; for 0.5 h;

Steps:

N-Methoxy-N-methylbenzamide (3a);^38,39Typical Procedure
General procedure: A solution of NHMe(OMe) (0.360 g, 6.0 mmol) and benzoic acid (0.244 g, 2.0 mmol) was stirred in dry toluene (10 mL) at 0 °C for 10 min. A solution of PCl₃ (0.137 g, 1.0 mmol) in dry toluene (2 mL) was then added dropwise to the mixture. The mixture was warmed to r.t. slowly and then stirred at 60 °C for 0.5 h. When the reaction was complete (TLC monitoring), the mixture was cooled to r.t. The mixture was then quenched with sat. NaHCO₃ soln (20 mL) and extracted with EtOAc (3 × 10 mL). The combined organic layers were dried (anhyd MgSO₄). The solvent was removed in vacuo.The product was purified by column chromatography (silica gel, petroleum ether-EtOAc, 3:2) to give pure 3a as a colorless oil; yield: 320 mg (97%).

References:

Niu, Teng;Wang, Ke-Hu;Huang, Danfeng;Xu, Changming;Su, Yingpeng;Hu, Yulai;Fu, Ying [Synthesis,2014,vol. 46,# 3,art. no. SS-2013-H0629-OP,p. 320 - 330]

589-18-4 Synthesis