Potassium Carbonate → HCID 53682248, compound

HRID 582285Notes

Reaction equation

HRID 582285 reaction equation
[C:1]([NH:4][C:5]1[CH:6]=[C:7]([CH:10]=[CH:11][CH:12]=1)[O:8][CH3:9])(=O)[CH3:2].BrC1C=[CH:25][C:17]([C:18]([N:20]([CH2:23][CH3:24])[CH2:21][CH3:22])=[O:19])=[CH:16][CH:15]=1.C([O-])([O-])=O.[K+].[K+]>C(Cl)Cl.[Cu]I>[CH2:23]([N:20]([CH2:21][CH3:22])[C:18](=[O:19])[C:17]1[CH:16]=[CH:15][C:1]([NH:4][C:5]2[CH:12]=[CH:11][CH:10]=[C:7]([O:8][CH3:9])[CH:6]=2)=[CH:2][CH:25]=1)[CH3:24]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 11494Acetamide, N-(3-methoxyphenyl)-HCID 44982544-bromo-N,N-diethylbenzamide

Product 1

HCID 53682248HCID 53682248, compoundYield 437.1%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
250 °C

Procedure

3.7 g (2.3 mmol) of N-acetyl-m-anisidine, 10.6 g (41.4 mmol) of 4-bromo-N,N-diethylbenzamide and 0.42 g of CuI were heated to 1000° C.; 3 g (22.3 mmol) of K2CO3 were added and the resulting mixture was heated to 250° C. for 2 hours. The residue was dissolved in CH2Cl2 and washed with H2O, the organic layer was dried over Na2SO4 and the solvent was removed in vacuo. The resulting residue was dissolved in 20 ml of absolute EtOH and refluxed for 2 h. The solvent was removed in vacuo, the residue was taken up in H2O and the aqueous layer extracted with AcOEt. The organic layer was dried over Na2SO4 and the solvent removed in vacuo. The resulting residue was purified by flash chromatography (AcOEt/Hexane 6:4), yielding 3 g of the title compound.

Workup

  1. washwashed with H2O
  2. dry with materialthe organic layer was dried over Na2SO4
  3. customthe solvent was removed in vacuo
  4. dissolutionThe resulting residue was dissolved in 20 ml of absolute EtOH
  5. temperaturerefluxed for 2 h
  6. customThe solvent was removed in vacuo
  7. extractionthe aqueous layer extracted with AcOEt
  8. dry with materialThe organic layer was dried over Na2SO4
  9. customthe solvent removed in vacuo
  10. customThe resulting residue was purified by flash chromatography (AcOEt/Hexane 6:4)

Sources & evidence

ORD record
ord-36fe5b3343364e368a41922def7450c9
Source dataset
uspto-grants-1999_07
Patent number
US05922887

Reaction notes

Loading…