2-Imidazolidinone → HCID 59299181, compound

HRID 2065514Notes

Reaction equation

HRID 2065514 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-dc0bab71dbd44ff385254f23c5bacba4
Source dataset
uspto-grants-2012_10
Patent number
US08288536B2

Reaction notes

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