Benzyl azide → HCID 13646828, compound

HRID 1982345Notes

Reaction equation

HRID 1982345 reaction equation
[Na].[C:2]([CH2:6][C:7]([O:9]CC)=[O:8])(=O)[CH2:3][CH3:4].[CH2:12]([N:19]=[N+:20]=[N-:21])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[OH-].[Na+]>C(O)C.O>[CH2:12]([N:19]1[C:2]([CH2:3][CH3:4])=[C:6]([C:7]([OH:9])=[O:8])[N:21]=[N:20]1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

7

Reactant 4

HCID 12152Benzyl azideHCID 14798Sodium HydroxideHCID 78656Ethyl 3-oxovalerateHCID 5360545Sodium

Product 1

HCID 13646828HCID 13646828, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a solution of 4.3 g (187 mmoles) of sodium pellets in 80 ml of absolute ethanol under nitrogen was added 18.0 g (125 mmoles) of ethyl propionylacetate followed by 16.6 g (125 mmoles) of benzyl azide. The resulting reaction mixture was stirred under reflux for two days. Upon cooling to room temperature, 45 ml of 4M aqueous sodium hydroxide was added dropwise and the mixture was refluxed for 3 hours. The reaction was again cooled to room temperature and concentration in vacuo gave a gummy solid. This residue was dissolved in 125 ml of water and extracted with ether. Acidification (pH 1) with 12N hydrochloric acid caused precipitation of 25.1 g (87%) of 1(2 or 3)-benzyl-5-ethyl-1H-1,2,3-triazole-4-carboxylic acid as a tan solid. The structure was confirmed by n.m.r. and I.R.

Workup

  1. customThe resulting reaction mixture
  2. temperatureunder reflux for two days
  3. temperaturethe mixture was refluxed for 3 hours
  4. temperatureThe reaction was again cooled to room temperature
  5. concentrationconcentration in vacuo
  6. customgave a gummy solid
  7. extractionextracted with ether
  8. customprecipitation of 25.1 g (87%) of 1(2 or 3)-benzyl-5-ethyl-1H-1,2,3-triazole-4-carboxylic acid as a tan solid

Sources & evidence

ORD record
ord-971292d5617c4e8bb53e1b163c46670f
Source dataset
uspto-grants-1986_06
Patent number
US04596596

Reaction notes

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