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

HRID 1710337Notes

Reaction equation

HRID 1710337 reaction equation
[O:1]=[C:2]1[NH:6][CH2:5][CH2:4][N:3]1[C:7]1[CH:16]=[CH:15][C:10]([C:11]([O:13][CH3:14])=[O:12])=[CH:9][CH:8]=1.[H-].[Na+].Br[CH2:20][C:21]1[CH:26]=[CH:25][C:24]([C:27]([CH3:30])([CH3:29])[CH3:28])=[CH:23][CH:22]=1>CN(C)C=O>[C:27]([C:24]1[CH:23]=[CH:22][C:21]([CH2:20][N:6]2[CH2:5][CH2:4][N:3]([C:7]3[CH:8]=[CH:9][C:10]([C:11]([O:13][CH3:14])=[O:12])=[CH:15][CH:16]=3)[C:2]2=[O:1])=[CH:26][CH:25]=1)([CH3:30])([CH3:28])[CH3:29]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 878361-(Bromomethyl)-4-(1,1-dimethylethyl)benzeneHCID 18526090Methyl 4-(2-oxoimidazolidin-1-yl)benzoate

Product 1

HCID 59456805Methyl 4-(3-(4-tert-butylbenzyl)-2-oxoimidazolidin-1-yl)benzoateYield 81%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

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).

Workup

  1. stirringAfter stirring 24 hours at room temperature
  2. customthe mixture was quenched with 1 ml water
  3. customthe solvents were removed under reduced pressure
  4. additionThe residue was diluted with ethyl acetate (50 ml)
  5. washwashed with water (50 ml) and brine (50 ml)
  6. customRemoval of the solvent
  7. customgave the residue which
  8. customwas purified on ISCO system (1% methanol in dichloromethane)

Sources & evidence

ORD record
ord-c030b172400a4be4859dbacf5239007e
Source dataset
uspto-grants-2010_09
Patent number
US07790707B2

Reaction notes

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