반응 #1797519

반응 방정식

1-(bromomethyl)-4-tert-butylbenzene

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

sodium hydride

→

product

수율 81.0%

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

수율 81.0%

용매

N,N-dimethylformamide

반응 조건

후처리

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

실험 절차

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).

출처