Water → HCID 68514467, compound

HRID 1717308Notes

Reaction equation

HRID 1717308 reaction equation
[N:1]([C:4]1[CH:14]=[CH:13][C:7]([C:8]([NH:10][CH2:11][CH3:12])=[O:9])=[CH:6][CH:5]=1)=[N+:2]=[N-:3].[C:15]([CH2:23][C:24]([O:26]CC)=[O:25])(=O)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.[O-]CC.[Na+].O>C(O)C>[CH2:11]([NH:10][C:8]([C:7]1[CH:6]=[CH:5][C:4]([N:1]2[C:15]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[C:23]([C:24]([OH:26])=[O:25])[N:3]=[N:2]2)=[CH:14][CH:13]=1)=[O:9])[CH3:12]

Participants

6

Reactant 4

HCID 962WaterHCID 7170Ethyl benzoylacetateHCID 2723922Sodium ethoxideHCID 594322264-azido-N-ethylbenzamide

Product 1

HCID 68514467HCID 68514467, compoundYield 98.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

4-Azido-N-ethylbenzamide (267 mg, 1.40 mmol) and ethyl benzoylacetate (0.316 ml, 1.75 mmol, 1.25 eq.) were dissolved in ethanol (8 ml), sodium ethoxide (122 mg, 1.75 mmol, 1.25 eq.) was added, and the mixture was stirred at room temperature for 30 min, and then at 60° C. for 13 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 (3:1, 40 ml). The organic layer was extracted with 2% aqueous sodium carbonate solution (20 ml). The aqueous layers were combined, acidified (pH<3) with 6N hydrochloric acid, and stood still at 0° C. The precipitate was collected by filtration, washed with water and dried to give the title compound as a pale-yellow powder (465 mg, 1.38 mmol, 98.8%).

Workup

  1. waitat 60° C. for 13 hr
  2. customwas evaporated
  3. additionthe residue was diluted with 2% aqueous sodium carbonate solution (20 ml)
  4. washwashed with ethyl acetate-hexane (3:1, 40 ml)
  5. extractionThe organic layer was extracted with 2% aqueous sodium carbonate solution (20 ml)
  6. customstood still at 0° C
  7. filtrationThe precipitate was collected by filtration
  8. washwashed with water
  9. customdried

Sources & evidence

ORD record
ord-2f9ea67f617040ad8c7c8e2393e46640
Source dataset
uspto-grants-2010_09
Patent number
US07803822B2

Reaction notes

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