反応 #1797519

反応方程式

1-(bromomethyl)-4-tert-butylbenzene

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

sodium hydride

→

product

収率 81.0%

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

収率 81.0%

溶媒

N,N-dimethylformamide

反応条件

後処理

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

実験手順

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).

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