Potassium Carbonate → HCID 18976189, compound

HRID 2393619Notes

Reaction equation

HRID 2393619 reaction equation
[CH2:1]([C:3]1[CH:4]=[C:5]([NH:9][C:10](=O)[CH3:11])[CH:6]=[CH:7][CH:8]=1)[CH3:2].C(=O)([O-])[O-].[K+].[K+].Br[C:20]1[CH:21]=[C:22]([O:26][CH3:27])[CH:23]=CC=1>[Cu]>[CH2:1]([C:3]1[CH:4]=[C:5]([NH:9][C:10]2[CH:11]=[CH:20][CH:21]=[C:22]([O:26][CH3:27])[CH:23]=2)[CH:6]=[CH:7][CH:8]=1)[CH3:2]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 169713-BromoanisoleHCID 4341261N-(3-ethylphenyl)acetamide

Product 1

HCID 18976189HCID 18976189, compoundYield 98.4%

Reagents, catalysts & solvents 1

HCID 23978CopperCatalyst

Conditions

Temperature
200 °C

Procedure

A mixture of 11 g of N-(3-ethylphenyl)acetamide, 9 g of copper powder, 19.8 g of potassium carbonate and 26.7 g of m-bromoanisole was stirred at 200° C. for 3 days. Insolubles were filtered off from the reaction mixture, and the filtrate was purified by silica gel column chromatography [ethyl acetate-hexane (1:3)]. To the resulting substance were added 16.6 g of potassium hydroxide, 8.7 ml of water and 170 ml of ethanol, and the whole was refluxed for 1 hour. The solvent was removed from the reaction mixture by evaporation, and water and ethyl acetate were added to the residue. After the organic layer was collected by separation, washed and dried, the solvent was removed by evaporation to afford 15.08 g of N-(3-ethylphenyl)-N-(3-methoxyphenyl)amine as an oil. IR (Nujol) (cm-1): 3400, 1600, 1490, 1460, MS (m/z): 227 (M+, base).

Workup

  1. filtrationInsolubles were filtered off from the reaction mixture
  2. customthe filtrate was purified by silica gel column chromatography [ethyl acetate-hexane (1:3)]
  3. additionTo the resulting substance were added 16.6 g of potassium hydroxide, 8.7 ml of water and 170 ml of ethanol
  4. temperaturethe whole was refluxed for 1 hour
  5. customThe solvent was removed from the reaction mixture by evaporation, and water and ethyl acetate
  6. additionwere added to the residue
  7. customAfter the organic layer was collected by separation
  8. washwashed
  9. customdried
  10. customthe solvent was removed by evaporation

Sources & evidence

ORD record
ord-66c855583c944efa9b0e717621fea797
Source dataset
uspto-grants-1998_09
Patent number
US05807883

Reaction notes

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