Diethyl Ether → HCID 57719285, compound

HRID 1985226Notes

Reaction equation

HRID 1985226 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:27]=[CH:28][C:29]=1[CH3:30])[CH2:5][N:6]1[C:10](=O)[CH:9]([CH2:12][CH2:13][CH2:14][C:15]2[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=2)[N:8]([CH2:23][CH2:24][CH3:25])[C:7]1=[O:26].[CH3:31][Mg]Br.CCOCC>C1COCC1>[CH3:1][C:2]1[CH:3]=[C:4]([CH:27]=[CH:28][C:29]=1[CH3:30])[CH2:5][N:6]1[C:10]([CH3:31])=[C:9]([CH2:12][CH2:13][CH2:14][C:15]2[CH:16]=[CH:17][C:18]([O:21][CH3:22])=[CH:19][CH:20]=2)[N:8]([CH2:23][CH2:24][CH3:25])[C:7]1=[O:26]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 57718945HCID 57718945, compoundHCID 178418573HCID 178418573, compound

Product 1

HCID 57719285HCID 57719285, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

A 0° C. solution of 3-(3,4-dimethyl-benzyl)-5-[3-(4-methoxy-phenyl)-propyl]-1-propyl-imidazolidine-2,4-dione (0.155 g, 0.379 mmol) in THF (6 mL) was treated dropwise with a 3 molar solution of methyl magnesium bromide in Et2O (0.76 mL, 2.28 mmol) and then stirred at 0° C. under N2 for 1 h. The reaction was quenched with 1 N HCl (5 mL) and stirred at room temperature for 15 minutes to effect elimination and then was worked up extractively with EtOAc and water. The organic layer dried (MgSO4), and the solvent removed in vacuo to afford 0.155 g (100%) 1-(3,4-dimethyl-benzyl)-4-[3-(4-methoxy-phenyl)-propyl]-5-methyl-3-propyl-1,3-dihydro-imidazol-2-one that was utilized without purification. MS (ES+) Calc'd for C26H35N2O2 (M+1) 407. Found m/z 407 (100%). 1H NMR.

Workup

  1. customThe reaction was quenched with 1 N HCl (5 mL)
  2. stirringstirred at room temperature for 15 minutes
  3. dry with materialThe organic layer dried (MgSO4)
  4. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-a5ec9508a8fd48b6a54bb48f4f4dba6f
Source dataset
uspto-grants-2009_06
Patent number
US07544812B2

Reaction notes

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