Benzyl azide → HCID 178525374, compound

HRID 1729661Notes

Reaction equation

HRID 1729661 reaction equation
[Na].[CH2:2]([N:9]=[N+:10]=[N-:11])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[C:12]([CH2:16][CH2:17][CH:18](C(OCC)=O)[C:19](OCC)=[O:20])([O:14]C)=[O:13]>C(O)C>[CH2:2]([N:9]1[C:19]([OH:20])=[C:18]([CH2:17][CH2:16][C:12]([OH:14])=[O:13])[N:11]=[N:10]1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 12152Benzyl azideHCID 2200681,1-Diethyl 3-methyl propane-1,1,3-tricarboxylateHCID 5360545Sodium

Product 1

HCID 178525374HCID 178525374, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 1.725 g. (75 mmol.) of sodium in 50 ml. of absolute ethanol is added 6.0 g. (45 mmol.) of benzylazide and 12.3 g. (50 mmol.) of diethyl 2-(carbomethoxyethyl)malonate. The reaction mixture is refluxed for 12 hours, then cooled and evaporated to dryness. Water (100 ml.) is added and the mixture is heated while maintaining the pH at 12. The aqueous mixture is extracted with ethyl acetate and the aqueous phase is acidified with 3N hydrochloric acid and extracted with ethyl acetate. The ethyl acetate solution is evaporated to dryness to give 1-benzyl-4-(2-carboxyethyl)-5-hydroxy-1,2,3-triazole.

Workup

  1. temperatureThe reaction mixture is refluxed for 12 hours
  2. temperaturecooled
  3. customevaporated to dryness
  4. additionWater (100 ml.) is added
  5. temperaturethe mixture is heated
  6. temperaturewhile maintaining the pH at 12
  7. extractionThe aqueous mixture is extracted with ethyl acetate
  8. extractionextracted with ethyl acetate
  9. customThe ethyl acetate solution is evaporated to dryness

Sources & evidence

ORD record
ord-40fbcbf0d51f4f64a61bfafc580cc842
Source dataset
uspto-grants-1976_11
Patent number
US03989694

Reaction notes

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