Potassium Carbonate → HCID 86607812, compound

HRID 1987037Notes

Reaction equation

HRID 1987037 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10]([NH:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[Cl:19])=[O:11])=[C:4]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2[Cl:26])[CH:3]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.[Cu]I>[Cl:1][C:2]1[N:7]=[C:6]2[C:5]([CH2:8][CH2:9][C:10](=[O:11])[N:12]2[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[Cl:19])=[C:4]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2[Cl:26])[CH:3]=1

Participants

5

Reactant 2

HCID 11430Potassium CarbonateHCID 86607813HCID 86607813, compound

Product 1

HCID 86607812HCID 86607812, compoundYield 115.6%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 6228DimethylformamideSolvent

Procedure

3-[6-Chloro-4-(2-chlorophenyl)-3-pyridinyl]-N-(2-chlorophenyl)propanamide (1.51 g, 3.43 mmol) was dissolved in DMF (40 ml), potassium carbonate (0.95 g, 6.87 mmol) and copper(I) iodide (1.3 g, 6.83 mmol) added and the mixture heated at reflux for 1 h. Most of the DMF was removed in vacuo, the residue was treated with water (10 ml) and brine (10 ml), and extracted with dichloromethane (2×15 ml) and ethyl acetate (15 ml). The extracts were passed through a hydrophobic frit and evaporated in vacuo to give the title compound as an off-white solid (1.6 g)

Workup

  1. temperaturethe mixture heated
  2. temperatureat reflux for 1 h
  3. customMost of the DMF was removed in vacuo
  4. additionthe residue was treated with water (10 ml) and brine (10 ml)
  5. extractionextracted with dichloromethane (2×15 ml) and ethyl acetate (15 ml)
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-8f2aae69606f42619ca384253de22044
Source dataset
uspto-grants-2009_06
Patent number
US07550480B2

Reaction notes

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