Reacción #1797519

Ecuación de reacción

1-(bromomethyl)-4-tert-butylbenzene

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

sodium hydride

→

product

Rendimiento 81.0%

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

Rendimiento 81.0%

Disolventes

N,N-dimethylformamide

Condiciones de reacción

Tratamiento posterior

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

Procedimiento

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).

Fuente