Water → HCID 68514308, compound

HRID 1717310Notes

Reaction equation

HRID 1717310 reaction equation
[C:1]([CH2:11][C:12]([O:14]CC)=[O:13])(=O)[CH:2]=[CH:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[N:17]([C:20]1[CH:30]=[CH:29][C:23]([C:24]([NH:26][CH2:27][CH3:28])=[O:25])=[CH:22][CH:21]=1)=[N+:18]=[N-:19].[O-]CC.[Na+].O>C(O)C>[CH2:27]([NH:26][C:24]([C:23]1[CH:29]=[CH:30][C:20]([N:17]2[C:1](/[CH:2]=[CH:3]/[C:4]3[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=3)=[C:11]([C:12]([OH:14])=[O:13])[N:19]=[N:18]2)=[CH:21][CH:22]=1)=[O:25])[CH3:28]

Participants

6

Reactant 4

HCID 962WaterHCID 2723922Sodium ethoxideHCID 54004396Ethyl cinnamoylacetateHCID 594322264-azido-N-ethylbenzamide

Product 1

HCID 68514308HCID 68514308, compoundYield 43.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

Ethyl cinnamoylacetate (1.17 g, 4.82 mmol, 1.2 eq.) obtained in Example 106a) and 4-azido-N-ethylbenzamide (0.750 g, 3.94 mmol) were dissolved in ethanol (25 ml), sodium ethoxide (373 mg, 4.93 mmol, 1.25 eq.) was added, and the mixture was stirred at room temperature for 30 min, and then at 60° C. for 10.5 hr. Water (20 ml) was added to the reaction mixture, ethanol was evaporated, and the residue was diluted with 2% aqueous sodium carbonate solution (20 ml) and washed with ethyl acetate-hexane (2:1, 50 ml). The organic layer was extracted with 2% aqueous sodium carbonate solution (20 ml). The aqueous layers were combined, washed with ethyl acetate-hexane (2:1, 40 ml), acidified (pH<3) with 6N hydrochloric acid, and extracted with ethyl acetate (25 ml×3). The organic layers were combined, washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated, and ethyl acetate was added. The precipitate was collected by filtration, washed with diethyl ether and dried to give the title compound as a pale-brown powder (627 mg, 1.73 mmol, 43.9%).

Workup

  1. waitat 60° C. for 10.5 hr
  2. customwas evaporated
  3. additionthe residue was diluted with 2% aqueous sodium carbonate solution (20 ml)
  4. washwashed with ethyl acetate-hexane (2:1, 50 ml)
  5. extractionThe organic layer was extracted with 2% aqueous sodium carbonate solution (20 ml)
  6. washwashed with ethyl acetate-hexane (2:1, 40 ml)
  7. extractionextracted with ethyl acetate (25 ml×3)
  8. washwashed with saturated brine
  9. dry with materialdried over anhydrous sodium sulfate
  10. concentrationconcentrated
  11. additionethyl acetate was added
  12. filtrationThe precipitate was collected by filtration
  13. washwashed with diethyl ether
  14. customdried

Sources & evidence

ORD record
ord-6802b5c493fc4c31af06ae3251488bd6
Source dataset
uspto-grants-2010_09
Patent number
US07803822B2

Reaction notes

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