Reaction #1797519

Reaction equation

1-(bromomethyl)-4-tert-butylbenzene

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

sodium hydride

→

product

Yield 81.0%

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

Yield 81.0%

Solvents

N,N-dimethylformamide

Conditions

Workup

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

Procedure

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).

Source