反应 #2286373

反应方程式

N-(1-methylcarbamoyl-ethyl)nicotinamide

Lawesson's reagent

→

desired product

收率 68.7%

methyl-(4-methyl-2-pyridin-3-yl-thiazol-5-yl)-amine

收率 68.7%

溶剂

DCE

反应条件

后处理

1. 1
   其他The reaction mixture was partitioned between CH2Cl2 and saturated aqueous sodium bicarbonate (NaHCO3)
2. 2
   其他The layers were separated
3. 3
   洗涤the organic layer was washed once with brine
4. 4
   干燥The solution was dried over MgSO4
5. 5
   过滤filtered
6. 6
   浓缩concentrated in vacuo
7. 7
   其他The crude material was purified by silica gel column chromatography (ethyl acetate)

实验过程

To a 10 mL microwave vessel containing DCE (5 mL) was added N-(1-methylcarbamoyl-ethyl)nicotinamide (207 mg, 1.0 mmol) followed by Lawesson's reagent (2,4-bis-(4-methoxyphenyl)-1,3-dithia-2,4-diphosphetane 2,4-disulfide, 404 mg, 1.0 mmol) in one portion. The heterogeneous mixture was heated in a microwave for 5 min at 130° C. The reaction mixture was partitioned between CH2Cl2 and saturated aqueous sodium bicarbonate (NaHCO3). The layers were separated and the organic layer was washed once with brine. The solution was dried over MgSO4, filtered and concentrated in vacuo. The crude material was purified by silica gel column chromatography (ethyl acetate) to give the desired product as an orange solid (141 mg, 68%): mp 84-87° C.; 1H NMR (300 MHz, CDCl3) δ 8.98 (d, J=1.7 Hz, 1H), 8.51 (dd, J=4.9, 1.7 Hz, 1H), 8.08 (dt, J=8.0, 1.7 Hz, 1H), 7.29 (m, 1H), 3.00 (s, 3H), 2.30 (s, 3H); ESIMS m/z 206.4 (M+1), m/z 204.2 (M−1).

来源