反应 #508690

反应方程式

triethylamine

2-amino-4-methoxymethoxymethyl-thiophene-3-sulfonic acid amide

3,3-diethoxy-acrylic acid ethyl ester

→

(7-methoxymethoxymethyl-1,1-dioxo-1,4-dihydro-1λ6-thieno[2,3-e][1,2,4]thiadiazin-3-yl)-acetic acid ethyl ester

收率 52.2%

溶剂

ethyl acetate

N,N-dimethylformamide

反应条件

后处理

1. 1
   workup.ADDITIONwas added to the mixture
2. 2
   温度It was then cooled to 25° C.
3. 3
   洗涤washed with 1.0 M aqueous hydrochloric acid solution (10 mL)
4. 4
   干燥The organic layer was dried over magnesium sulfate
5. 5
   过滤filtered
6. 6
   浓缩concentrated in vacuo
7. 7
   其他The residue was purified via flash column chromatography (Teledyne Isco RediSep column; 0-80% ethyl acetate in hexanes)

实验过程

To a solution of 2-amino-4-methoxymethoxymethyl-thiophene-3-sulfonic acid amide (0.76 g, 3.01 mmol) in N,N-dimethylformamide (10 mL) at 25° C. was added 3,3-diethoxy-acrylic acid ethyl ester (0.68 g, 3.61 mmol). The reaction was stirred at 70° C. for 5 h before triethylamine (1.68 mL, 12.04 mmol) was added to the mixture. The reaction was stirred at 70° C. overnight. It was then cooled to 25° C., diluted with ethyl acetate (10 mL) and washed with 1.0 M aqueous hydrochloric acid solution (10 mL). The organic layer was dried over magnesium sulfate, filtered and concentrated in vacuo. The residue was purified via flash column chromatography (Teledyne Isco RediSep column; 0-80% ethyl acetate in hexanes) to afford the desired product, (7-methoxymethoxymethyl-1,1-dioxo-1,4-dihydro-1λ6-thieno[2,3-e][1,2,4]thiadiazin-3-yl)-acetic acid ethyl ester (0.55 g, 1.57 mmol, 52%), as a brown oil. 1H NMR (400 MHz, CDCl3) δ: 1.32 (3H, t, J=7.2 Hz), 3.42 (3H, s), 3.68 (2H, s), 4.26 (2H, q, J=7.2 Hz), 4.76 (2H, s), 4.80 (2H, s), 7.00 (1H, s), 8.00 (1H, s).

来源