Hydrochloric Acid → ethyl 2-(4-cyano-1H-1,2,3-triazol-1-yl)acetate

HRID 876678Notes

Reaction equation

HRID 876678 reaction equation
[CH2:1]([O:3][C:4](=[O:9])[CH2:5][N:6]=[N+:7]=[N-:8])[CH3:2].Cl[C:11](=[CH2:14])[C:12]#[N:13].Cl>O>[CH2:1]([O:3][C:4](=[O:9])[CH2:5][N:6]1[CH:14]=[C:11]([C:12]#[N:13])[N:8]=[N:7]1)[CH3:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 69480Acetic acid, azido-, ethyl esterHCID 701982-Chloroacrylonitrile

Product 1

HCID 54053451ethyl 2-(4-cyano-1H-1,2,3-triazol-1-yl)acetate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

4.1 g (31.9 mmol) azidoacetic acid ethyl ester and 2.8 g (31.9 mmol) 2-chloroacrylonitrile are stirred in 32 ml water at a bath temperature of 80° C. for 16 h. After cooling to RT, the solution is rendered acid with 1 N hydrochloric acid and extracted with ethyl acetate. The organic phase is dried over sodium sulfate, filtered and concentrated in vacuo. 50 ml ethanol and 10 drops of conc. sulfuric acid are added to the residue and the mixture is stirred under reflux for 16 h. For working up, the reaction mixture is concentrated in vacuo, ethyl acetate is added to the residue, the suspension is washed with half-concentrated sodium bicarbonate solution and the organic phase is dried over sodium sulfate. The solvent is removed completely on a rotary evaporator and the solid is dried in vacuo.

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe organic phase is dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. addition50 ml ethanol and 10 drops of conc. sulfuric acid are added to the residue
  6. temperatureunder reflux for 16 h
  7. concentrationthe reaction mixture is concentrated in vacuo, ethyl acetate
  8. additionis added to the residue
  9. washthe suspension is washed with half-concentrated sodium bicarbonate solution
  10. dry with materialthe organic phase is dried over sodium sulfate
  11. customThe solvent is removed completely on a rotary evaporator
  12. customthe solid is dried in vacuo

Sources & evidence

ORD record
ord-fdc2d8fb4ab048d780ac59f07e39fcb9
Source dataset
uspto-grants-2015_03
Patent number
US08987261B2

Reaction notes

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