2-Imidazolidinone → HCID 59299181, compound

HRID 2234841Notes

Reaction equation

HRID 2234841 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH2:5]Br.[NH:10]1[CH2:14][CH2:13][NH:12][C:11]1=[O:15].C(=O)([O-])[O-].[K+].[K+]>CC(O)C>[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH2:5][N:10]1[CH2:14][CH2:13][NH:12][C:11]1=[O:15]

Participants

5

Reactant 3

HCID 84532-ImidazolidinoneHCID 11430Potassium CarbonateHCID 699793-Bromobenzyl bromide

Product 1

HCID 59299181HCID 59299181, compoundYield 44%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

3-Bromobenzyl bromide (1.0 g, 4.0 mmol) was added to a solution of 2-imidazolidone (1.03 g, 12.0 mmol) and potassium carbonate (1.66 g, 12.0 mmol) in 2-propanol (10 mL), and the reaction stirred at reflux for 40 h. The cooled solution was partitioned between EtOAc and water. Organics were washed with brine, dried (MgSO4) and concentrated in vacuo. Purification by silica gel chromatography (100% EtOAc) gave 446 mg (44%) of the title compound as a white solid. 1H NMR (400 MHz, MeOD-d4) δ 7.40-7.48 (m, 2H), 7.21-7.28 (m, 2H), 4.30 (s, 2H), 3.29-3.41 (m, 4H). [M+H] calc'd for C10H11BrN2O, 255, 257; found, 255, 257.

Workup

  1. temperatureat reflux for 40 h
  2. customThe cooled solution was partitioned between EtOAc and water
  3. washOrganics were washed with brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated in vacuo
  6. customPurification by silica gel chromatography (100% EtOAc)

Sources & evidence

ORD record
ord-d85cd3f994ec465fb7355b492f73730d
Source dataset
uspto-grants-2010_05
Patent number
US07713973B2

Reaction notes

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