HCID 22098558, compound → HCID 22098569, compound

HRID 266221Notes

Reaction equation

HRID 266221 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:12][CH2:11][N:10]([C:13]3[CH:18]=[CH:17][C:16]([CH2:19][CH2:20][C:21]([O:23][CH3:24])=[O:22])=[CH:15][CH:14]=3)[C:9]2=[O:25])=[C:4]([CH3:26])[CH:3]=1.[Cu][C:28]#[N:29]>CN(C)C=O>[C:28]([C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:12][CH2:11][N:10]([C:13]3[CH:18]=[CH:17][C:16]([CH2:19][CH2:20][C:21]([O:23][CH3:24])=[O:22])=[CH:15][CH:14]=3)[C:9]2=[O:25])=[C:4]([CH3:26])[CH:3]=1)#[N:29]

Participants

4

Reactant 2

HCID 22098558HCID 22098558, compoundHCID 178418546HCID 178418546, compound

Product 1

HCID 22098569HCID 22098569, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3.0 g of 1-(4-bromo-2-methyl-phenyl)-3-[4-(2-methoxycarbonyl-ethyl)-phenyl]-imidazolidin-2-one and 1.3 g of copper(I)cyanide were heated in 10 ml of dimethylformamide for 10 hours at a bath temperature of 175° C. The dimethylformamide was evaporated off in vacuo, the residue was digested with chloroform and filtered off. The chloroform solution was washed with water and saturated saline solution and concentrated by evaporation. The residue was purified by column chromatography (silica gel; methylene chloride/ethyl acetate=100:2)

Workup

  1. customThe dimethylformamide was evaporated off in vacuo
  2. filtrationfiltered off
  3. washThe chloroform solution was washed with water and saturated saline solution
  4. concentrationconcentrated by evaporation
  5. customThe residue was purified by column chromatography (silica gel; methylene chloride/ethyl acetate=100:2)

Sources & evidence

ORD record
ord-c9fa22e0d5c24322a75b01134ff900cc
Source dataset
uspto-grants-1997_07
Patent number
US05650424

Reaction notes

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