Potassium Carbonate → 3-(4-tert-butylphenyl)-N-(3,4-dimethoxyphenyl)acrylamide

HRID 730257Notes

Reaction equation

HRID 730257 reaction equation
[C:1]([C:5]1[CH:15]=[CH:14][C:8](/[CH:9]=[CH:10]/[C:11]([OH:13])=O)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].C(Cl)(=O)C(Cl)=O.[CH3:22][O:23][C:24]1[CH:25]=[C:26]([CH:28]=[CH:29][C:30]=1[O:31][CH3:32])[NH2:27].C(=O)([O-])[O-].[K+].[K+]>CCOC(C)=O.CC(C)=O.O.CN(C=O)C.C(Cl)Cl>[CH3:22][O:23][C:24]1[CH:25]=[C:26]([NH:27][C:11](=[O:13])/[CH:10]=[CH:9]/[C:8]2[CH:7]=[CH:6][C:5]([C:1]([CH3:2])([CH3:3])[CH3:4])=[CH:15][CH:14]=2)[CH:28]=[CH:29][C:30]=1[O:31][CH3:32]

Participants

10

Reactant 4

HCID 11430Potassium CarbonateHCID 227703,4-DimethoxyanilineHCID 65578Oxalyl chlorideHCID 7248394-(Tert-butyl)cinnamic acid

Product 1

HCID 101499553-(4-tert-butylphenyl)-N-(3,4-dimethoxyphenyl)acrylamide

Reagents, catalysts & solvents 5

HCID 180AcetoneSolventHCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a 20 mL round-bottomed flask equipped with reflux condenser and drying tube was added 4-tert-butyl-trans-cinnamic acid (200 mg, 0.98 mmol, EMKA-Chemie) followed by CH2Cl2 (5 mL), oxalyl chloride (90 uL, 130 mg, 1.03 mmol, Aldrich) and DMF (1 uL). The reaction mixture was magnetically stirred and heated at reflux for 30 min. The reaction mixture was concentrated in vacuo and the residue dissolved in acetone (2 mL). The solution was added to a mixture of 3,4-dimethoxyaniline (180 mg, 1.17 mmol, Aldrich), potassium carbonate (200 mg), water (2 mL) and acetone (2 mL), magnetically stirred at 25° C. in a 10 mL glass vial. The reaction mixture was stirred at 25° C. for 16 h then diluted with EtOAc (60 mL) and washed successively with 1 N HCl (20 mL), 1 N NaOH (20 mL), water (20 mL) and satd NaCl (20 mL), dried over MgSO4, filtered and concentrated. Recrystallization from hexane and CH2Cl2 provided the title product as a yellow solid. MP 115-116° C. MS (ESI, pos. ion) m/z: 340 (M+1).

Workup

  1. customTo a 20 mL round-bottomed flask equipped
  2. temperaturewith reflux condenser
  3. customdrying tube
  4. temperatureheated
  5. temperatureat reflux for 30 min
  6. concentrationThe reaction mixture was concentrated in vacuo
  7. dissolutionthe residue dissolved in acetone (2 mL)
  8. stirringThe reaction mixture was stirred at 25° C. for 16 h
  9. washwashed successively with 1 N HCl (20 mL), 1 N NaOH (20 mL), water (20 mL) and satd NaCl (20 mL)
  10. dry with materialdried over MgSO4
  11. filtrationfiltered
  12. concentrationconcentrated
  13. customRecrystallization from hexane and CH2Cl2

Sources & evidence

ORD record
ord-c9da0f1e7c22481a994f11a0ad9ba582
Source dataset
uspto-grants-2009_09
Patent number
US07582657B2

Reaction notes

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