3,N-DIMETHOXY-N-METHYLBENZAMIDE synthesis
- Product Name:3,N-DIMETHOXY-N-METHYLBENZAMIDE
- CAS Number:152121-82-9
- Molecular formula:C10H13NO3
- Molecular Weight:195.22
Yield:152121-82-9 100%
Reaction Conditions:
with 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride;triethylamine in dichloromethane at 20; for 18 h;
Steps:
To a stirred solution of 3-methoxybenzoic acid (10.0 g, 65.7 mmol) in CH2Cl2 (300 mL) were added N, O-dimethylhydroxylaminehydrochloride (7.00 g, 71.8mmol), triethylamine (11.9 mL, 85.4 mmol), and EDCI?HCl(18.9 g, 98.6 mmol). After stirring for 18 h at room temperature, the reaction was quenched with sat. NaHCO3 aq., and the resulting mixture was extracted with EtOAc. The organic layer was washed with water followed by brine, dried over Na2SO4,and concentrated in vacuo to givethe titlecompound (12.8 g, 65.7 mmol, quant.) as a yellow oil. 1H-NMR(400 MHz, CDCl3):? δ 3.36 (3H, s), 3.58 (3H, s), 3.83 (3H, s),6.98-7.01 (1H, m), 7.20-7.25 (2H, m), 7.31 (1H, t, J = 7.9 Hz).
References:
Ochiai, Koji;Takita, Satoshi;Kojima, Akihiko;Eiraku, Tomohiko;Iwase, Kazuhiko;Kishi, Tetsuya;Ohinata, Akira;Yageta, Yuichi;Yasue, Tokutaro;Adams, David R.;Kohno, Yasushi [Bioorganic and Medicinal Chemistry Letters,2013,vol. 23,# 1,p. 375 - 381] Location in patent:supporting information
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