反応 #167182

反応方程式

isopropylamine

phenylisothiocyanate

pyridine

methyl bromoacetate

HCl

→

3-phenyl-2-[(Z)-isopropylimino]-thiazolidin-4-one

溶媒

methanol

反応条件

後処理

1. 1
   温度The solution which becomes slightly warm during the addition
2. 2
   workup.ADDITIONis added
3. 3
   抽出extracted with diethyl ether (150 mL)
4. 4
   workup.ADDITIONby adding sat. aq. NaHCO3
5. 5
   抽出extracted with diethyl ether (4×150 mL)
6. 6
   乾燥The organic extracts are dried over MgSO4
7. 7
   その他evaporated
8. 8
   ろ過filtered off
9. 9
   洗浄washed with additional diethyl ether/heptane
10. 10
    その他dried

実験手順

To a solution of isopropylamine (1.31 g, 22.19 mmol) in methanol (25 mL) is added portionwise phenylisothiocyanate (3.0 g, 22.19 mmol). The solution which becomes slightly warm during the addition is stirred at rt for 4 h before pyridine (2.63 g, 33.29 mmol) and methyl bromoacetate (3.39 g, 22.19 mmol) is added. The mixture is stirred for another 16 h at rt before it is poured onto 1 N aq. HCl (100 mL) and extracted with diethyl ether (150 mL). The aq. layer is neutralised by adding sat. aq. NaHCO3 and extracted with diethyl ether (4×150 mL). The organic extracts are dried over MgSO4 and evaporated. The remaining solid is suspended in diethyl ether/heptane, filtered off, washed with additional diethyl ether/heptane and dried to give 3-phenyl-2-[(Z)-isopropylimino]-thiazolidin-4-one.

出典