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

HRID 2039469Notes

Reaction equation

HRID 2039469 reaction equation
[N:1]([CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6])=[N+:2]=[N-:3].Cl[C:11](=[CH2:14])[C:12]#[N:13].Cl>O>[C:12]([C:11]1[N:3]=[N:2][N:1]([CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6])[CH:14]=1)#[N:13]

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) of ethyl azidoacetate and 2.8 g (31.9 mmol) of 2-chloroacrylonitrile are stirred in 32 ml of water at a bath temperature of 80° C. for 16 h. After cooling to RT, the solution is acidified with 1 N hydrochloric acid and extracted with ethyl acetate. The organic phase is dried over sodium sulphate, filtered and concentrated under reduced pressure. 50 ml of ethanol and 10 drops of concentrated sulphuric acid are added to the residue, and the mixture is stirred under reflux for 16 h. For work-up, the reaction mixture is concentrated under reduced pressure, ethyl acetate is added to the residue, the suspension is washed with semiconcentrated sodium bicarbonate solution and the organic phase is dried over sodium sulphate. The solvent is removed completely on a rotary evaporator and the solid is dried under reduced pressure. Yield: 1.5 g (25% of theory)

Workup

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

Sources & evidence

ORD record
ord-97c3c9f96b3643488938ebf65b7d0f35
Source dataset
uspto-grants-2013_11
Patent number
US08580778B2

Reaction notes

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