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80783-98-8

N-Methoxy-N-MethylcyclohexanecarboxaMide synthesis

12synthesis methods
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Yield:80783-98-8 97%

Reaction Conditions:

Stage #1: N,0-dimethylhydroxylamine;Cyclohexanecarboxylic acid 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);38,39 Typical 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]