N-methoxy-N,3-dimethylthiophene-2-carboxamide synthesis
- Product Name:N-methoxy-N,3-dimethylthiophene-2-carboxamide
- CAS Number:181868-50-8
- Molecular formula:C8H11NO2S
- Molecular Weight:185.24
61341-26-2
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Yield:181868-50-8 100%
Reaction Conditions:
with triethylamine in chloroform at 0 - 20;Inert atmosphere;
Steps:
4.2.56. Synthesis of N-methoxy-N,3-dimethylthiophene-2-carboxamide (43)
To a mixture of N,O-dimethylhydroylamine hydrochloride (5.85 g, 60 mmol) and TEA (16.7 mL, 120 mmol) in chloroform was added 3-methylthiophene-2-carbonyl chloride (42, 4.89 mL, 40 mmol) at 0 °C. Then, the reaction temperature was raised to room temperature, and maintained for overnight. The reaction mixture was subsequently washed with aq HCl solution (1 M, 50 mL) and brine. The organic phase was dried MgSO4 and evaporated under vacuum to provide the intermediate 43 (7.47 g, ～100%) as a yellow oil, which was used without further purification. 1H NMR (400 MHz, CDCl3) δ 7.37 (d, J = 5.2 Hz, 1H), 6.90 (d, J = 5.2 Hz, 1H), 3.71 (s, 3H), 3.34 (s, 3H), 2.55 (s, 3H); MS calcd for C8H11NO2S (MW 185.24), found [M+H]+ 186.
References:
Lee, Suk Ho;Song, Kwang-Seop;Kim, Jong Yup;Kang, Misuk;Lee, Jun Sung;Cho, Seung-Hwan;Park, Hyun-Ju;Kim, Jeongmin;Lee, Jinhwa [Bioorganic and Medicinal Chemistry,2011,vol. 19,# 19,p. 5813 - 5832] Location in patent:experimental part
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