Water → HCID 67395719, compound

HRID 470606Notes

Reaction equation

HRID 470606 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:11]=[CH:12][C:13]([OH:15])=O)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].C(N1C=CN=C1)(N1C=CN=C1)=O.O[NH:29][C:30](=[NH:38])[CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1.O>CN(C=O)C>[CH2:31]([C:30]1[N:38]=[C:13]([CH:12]=[CH:11][C:5]2[CH:6]=[CH:7][C:8]([O:9][CH3:10])=[C:3]([O:2][CH3:1])[CH:4]=2)[O:15][N:29]=1)[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1

Participants

6

Reactant 4

HCID 962WaterHCID 168483',4'-Dimethoxycinnamic acidHCID 682631,1'-CarbonyldiimidazoleHCID 178510798HCID 178510798, compound

Product 1

HCID 67395719HCID 67395719, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3-(3,4-Dimethoxy-phenyl)-acrylic acid (compound of Example 2, Method A, Step 1; 2.0 g, 9.6 mmol) was dissolved in DMF (20 mL) to which 1,1′-carbonyldiimidazole (CDI) (1.71 g, 10.56 mmol) was added and the reaction mixture was stirred at room temperature. At the end of 3 h, N-hydroxy-2-phenyl-acetamidine (1.58 g, 10.56 mmol) was added and the reaction mixture was stirred at room temperature for 8 h. After the completion of the reaction, additional CD (1.71 g, 10.56 mmol) was added and the reaction mixture was refluxed at 110° C. to 120° C. for 8 h to effect cyclodehydration. DMF was evaporated and the residue obtained was cooled to room temperature followed by addition of water (15 mL). The resulting mixture was extracted with ethyl acetate (3×10 mL). The combined organic layers were washed with water (2×10 mL) and brine (10 mL). The organic phase obtained was dried over anhydrous sodium sulfate and concentrated to afford the title compound.

Workup

  1. additionwas added
  2. stirringthe reaction mixture was stirred at room temperature for 8 h
  3. customAfter the completion of the reaction, additional CD (1.71 g, 10.56 mmol)
  4. additionwas added
  5. temperaturethe reaction mixture was refluxed at 110° C. to 120° C. for 8 h
  6. customDMF was evaporated
  7. customthe residue obtained
  8. temperaturewas cooled to room temperature
  9. extractionThe resulting mixture was extracted with ethyl acetate (3×10 mL)
  10. washThe combined organic layers were washed with water (2×10 mL) and brine (10 mL)
  11. customThe organic phase obtained
  12. dry with materialwas dried over anhydrous sodium sulfate
  13. concentrationconcentrated

Sources & evidence

ORD record
ord-1eebe77d2a374c9783c401590cfc61ba
Source dataset
uspto-grants-2014_01
Patent number
US08629277B2

Reaction notes

Loading…