反応 #1583815

反応方程式

4-[2-ethyl-4-(4-fluorophenyl)-1,3-thiazol-5-yl]pyridine 1-oxide

phosphoryl chloride

→

2-Chloro-4-[2-ethyl-4-(4-fluorophenyl)-1,3-thiazol-5-yl]pyridine

反応条件

後処理

1. 1
   温度is heated
2. 2
   温度under reflux
3. 3
   濃縮the reaction mixture is concentrated under reduced pressure
4. 4
   workup.ADDITION50 ml of ice-water are added
5. 5
   その他The organic phase is separated off
6. 6
   洗浄once more washed with 50 ml of water
7. 7
   乾燥dried over MgSO4
8. 8
   その他The residue is then purified by column chromatography on silica gel (cyclohexane/ethyl acetate)

実験手順

A mixture of 1.90 g (6.33 mmol) of 4-[2-ethyl-4-(4-fluorophenyl)-1,3-thiazol-5-yl]pyridine 1-oxide and 40 ml of phosphoryl chloride is heated under reflux. After 8 h, the reaction mixture is concentrated under reduced pressure, the residue is taken up in 150 ml of dichloromethane and 50 ml of ice-water are added. The organic phase is separated off and once more washed with 50 ml of water, dried over MgSO4 and freed from the solvent under reduced pressure. The residue is then purified by column chromatography on silica gel (cyclohexane/ethyl acetate). This gives 1.35 g (65%) of the desired product; 1H-NMR(DMSO-d6) δ: 8.35 (d, 1H), 7.49 (m, 2H), 7.35 (s, 1H), 7.25 (d, 1H), 7.19 (m, 2H), 3.06 (q, 2H), 1.37 (t, 3H).

出典