Dichloromethane → HCID 71252328, compound

HRID 2411182Notes

Reaction equation

HRID 2411182 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:10]=[CH:9][C:8](B(O)O)=[CH:7][CH:6]=1)=[O:4].[C:14]([N:17]1[CH2:21][CH2:20][NH:19][C:18]1=[O:22])(=[O:16])[CH3:15].C(Cl)Cl.C(N(CC)CC)C>C([O-])(=O)C.[Cu+2].C([O-])(=O)C.O>[C:14]([N:17]1[CH2:21][CH2:20][N:19]([C:8]2[CH:9]=[CH:10][C:5]([C:3]([O:2][CH3:1])=[O:4])=[CH:6][CH:7]=2)[C:18]1=[O:22])(=[O:16])[CH3:15]

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 8471TriethylamineHCID 79350N-AcetylimidazolidinoneHCID 27343694-Methoxycarbonylphenylboronic acid

Product 1

HCID 71252328HCID 71252328, compoundYield 16.4%

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 962WaterSolvent

Procedure

To a mixture of p-(methoxycarbonyl)phenylboronic acid (2.45 g), 1-acetylimidazolidin-2-one (870 mg) and copper(II) acetate (1.23 g) were added methylene chloride (20 mL) and triethylamine (1.9 mL), and the mixture was stirred at room temperature overnight. Water was added to the reaction mixture, and the insoluble material was collected by filtration. The filtrate was extracted with chloroform, and the solvent was evaporated from the organic layer. The obtained residue was purified by column chromatography (chloroform) to give the title compound (292 mg).

Workup

  1. filtrationthe insoluble material was collected by filtration
  2. extractionThe filtrate was extracted with chloroform
  3. customthe solvent was evaporated from the organic layer
  4. customThe obtained residue was purified by column chromatography (chloroform)

Sources & evidence

ORD record
ord-8d2fbb0b18ca47b09af49f4afc7bf3bc
Source dataset
uspto-grants-2014_08
Patent number
US08816079B2

Reaction notes

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