HCID 22098558, compound → HCID 22098569, compound

HRID 1459087Notes

Reaction equation

HRID 1459087 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-5d0dff2eba424e4492c4c9798a7e6d1b
Source dataset
uspto-grants-1998_12
Patent number
US05852192

Reaction notes

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