ChemicalBook CAS DataBase List 3,N-DIMETHOXY-N-METHYLBENZAMIDE

3,N-DIMETHOXY-N-METHYLBENZAMIDE synthesis

6synthesis methods

Product Name:3,N-DIMETHOXY-N-METHYLBENZAMIDE
CAS Number:152121-82-9
Molecular formula:C10H13NO3
Molecular Weight:195.22

6638-79-5 Synthesis

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586-38-9 Synthesis

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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

6638-79-5 Synthesis

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