反应 #1797519

反应方程式

1-(bromomethyl)-4-tert-butylbenzene

methyl 4-(2-oxoimidazolidin-1-yl)benzoate

sodium hydride

→

product

收率 81.0%

Methyl 4-(3-(4-tert-butylbenzyl)-2-oxoimidazolidin-1-yl)benzoate

收率 81.0%

溶剂

N,N-dimethylformamide

反应条件

后处理

1. 1
   workup.STIRRINGAfter stirring 24 hours at room temperature
2. 2
   其他the mixture was quenched with 1 ml water
3. 3
   其他the solvents were removed under reduced pressure
4. 4
   workup.ADDITIONThe residue was diluted with ethyl acetate (50 ml)
5. 5
   洗涤washed with water (50 ml) and brine (50 ml)
6. 6
   其他Removal of the solvent
7. 7
   其他gave the residue which
8. 8
   其他was purified on ISCO system (1% methanol in dichloromethane)

实验过程

To a solution of methyl 4-(2-oxoimidazolidin-1-yl)benzoate (440 mg, 2.0 mmol) in N,N-dimethylformamide (10 ml) at 0° C. was added sodium hydride (96 mg-60% in oil, 2.4 mmole). The resulting mixture was stirred for 1 hour followed by addition of 1-(bromomethyl)-4-tert-butylbenzene (545 mg, 2.4 mmol). After stirring 24 hours at room temperature, the mixture was quenched with 1 ml water and the solvents were removed under reduced pressure. The residue was diluted with ethyl acetate (50 ml) and washed with water (50 ml) and brine (50 ml). Removal of the solvent gave the residue which was purified on ISCO system (1% methanol in dichloromethane) to give a pure product as a white solid (593 mg, 81%): 1H NMR (400 MHz, CDCl3) δ 8.25 (d, 2H), 7.68 (d, 2H), 7.36 (d, 2H), 7.23 (d, 2H), 4.46 (s, 2H), 3.90 (s, 3H), 3.83 (dd, 2H), 3.43 (dd, 2H), 1.31 (s, 9H). MS (ESI) m/z: Calculated: 366.19; Observed: 367.1 (M++1).

来源