ChemicalBook CAS DataBase List N-ETHYLBENZAMIDE

N-ETHYLBENZAMIDE synthesis

13synthesis methods

Product Name:N-ETHYLBENZAMIDE
CAS Number:614-17-5
Molecular formula:C9H11NO
Molecular Weight:149.19

24948-82-1 Synthesis

24948-82-1
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108-88-3
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614-17-5
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$172.00/50mg

Yield:614-17-5 241 mg

Reaction Conditions:

with tert.-butylhydroperoxide;tetra-(n-butyl)ammonium iodide in water;acetonitrile at 80; for 0.416667 h;Flow reactor;Green chemistry;

Steps:

4.2. General procedure

General procedure: 5 mmol of amine (1) was dissolved in 50 mL CH3CN, which was placed into syringe A. And 5 mmol of N-Chlorosuccinimide (NCS) was dissolved in 50 mL CH3CN, which was placed into syringe B. Methylarene (2, 25 mmol, 10 eq.), tert-butylammonium iodide (TBAI, 2.5 mmol,1 eq.) and TBHP (70 wt% in water,12.5 mmol, 5 eq.) were dissolves in 50 mL CH3CN/H2O (CH3CN:H2O 4:1), which was placed into syringe C. The flow rate of syringes A, B and C were 0.1 mL/min, 0.1 mL/min, and 0.2 mL/min, respectively. And the temperature of the two oil baths was set in 50 °C and 80 °C, respectively. The reaction liquid was collected, and then quenched by NaHSO3 solution and extracted with ethyl acetate, washed with H2O. The organic layer was dried over anhydrous sodium sulfate and solvent was removed under vacuum. And the crude product was purified by flash chromatography on silica gel by gradient elution with ethyl acetate in petroleum ether to obtain the product

References:

Fang, Zheng;Guo, Kai;He, Wei;Liu, Chengkou;Shi, Tingting;Yang, Yuhang;Yang, Zhao;Zhang, Zhimin [Tetrahedron,2020,vol. 76,# 13] Location in patent:supporting information