Potassium Carbonate → HCID 67383896, compound

HRID 408110

Reaction equation

HRID 408110 reaction equation
[CH2:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[NH:9][C:10](=[O:12])[CH3:11])[CH3:2].C([O-])([O-])=O.[K+].[K+].Br[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[CH2:26][CH3:27]>[Cu]Br>[CH2:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[N:9]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[CH2:26][CH3:27])[C:10](=[O:12])[CH3:11])[CH3:2]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 160891-Bromo-2-ethylbenzeneHCID 36332O-Ethylacetanilide

Product 1

HCID 67383896HCID 67383896, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 24593copper(I) bromideCatalyst

Conditions

Temperature
200 °C

Procedure

The mixture of the N-(2-ethylphenyl)acetamide (7.35 g, 45.03 mmol), anhydrous K2CO3 (6.22 g, 45.03 mmol), copper(I) bromide (452.2 mg, 3.15 mmol) in 1-bromo-2-ethylbenzene was stirred and heated to 200° C. under argon for 48 h. After cooling the reaction mixture was poured into ice-H2O and extracted with ethyl acetate (2×500 mL), the combined organics were washed with brine, dried over anhydrous (K2CO3), filtered and concentrated to dryness. The crude product was purified using an ISCO machine using a ethyl acetate-hexane gradient to afford the product, N,N-bis(2-ethylphenyl)acetamide (8.1 g, 67%).

Workup

  1. temperatureAfter cooling the reaction mixture
  2. extractionextracted with ethyl acetate (2×500 mL)
  3. washthe combined organics were washed with brine
  4. dry with materialdried over anhydrous (K2CO3)
  5. filtrationfiltered
  6. concentrationconcentrated to dryness
  7. customThe crude product was purified

Sources & evidence

ORD record
ord-c6783476024348b39cf8721dedd375c9
Source dataset
uspto-grants-2014_06
Patent number
US08759336B2

Linked notes

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