Ethyl bromoacetate → ETHYL 2-(1H-1,2,3-TRIAZOL-1-YL)ACETATE

HRID 242257Notes

Reaction equation

HRID 242257 reaction equation
[Na].[NH:2]1[CH:6]=[CH:5][N:4]=[N:3]1.Br[CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10]>C(O)C>[CH2:12]([O:11][C:9](=[O:10])[CH2:8][N:2]1[CH:6]=[CH:5][N:4]=[N:3]1)[CH3:13]

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 5360545SodiumHCID 178418936HCID 178418936, compound

Product 1

HCID 10103365ETHYL 2-(1H-1,2,3-TRIAZOL-1-YL)ACETATE

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

129.2 g (5.6 mol) sodium are slowly added to 4.0 liters ethanol. 400.0 g (5.6 mol) 1,2,3-1H-triazole are then added and 623 ml (938.2 g, 5.6 mol) ethyl bromoacetate are added dropwise at an internal temperature of 20-25° C. The mixture is stirred at RT for 48 h. The solid which has precipitated out is filtered off, the ethanol is removed in vacuo and the mixture is filtered again. The residue is taken up in ethyl acetate, the mixture is filtered and is concentrated in vacuo again and the residue is purified by distillation over a 30 cm column. The product is obtained at a bath temperature of 140° C., an overhead temperature of 60-115° C. and a pressure of 1 mbar.

Workup

  1. customThe solid which has precipitated out
  2. filtrationis filtered off
  3. customthe ethanol is removed in vacuo
  4. filtrationthe mixture is filtered again
  5. filtrationthe mixture is filtered
  6. concentrationis concentrated in vacuo again
  7. distillationthe residue is purified by distillation over a 30 cm column
  8. customThe product is obtained at a bath temperature of 140° C.
  9. customan overhead temperature of 60-115° C.

Sources & evidence

ORD record
ord-21d40e77427f4d57b248ffd8911826b4
Source dataset
uspto-grants-2014_02
Patent number
US08653111B2

Reaction notes

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