Acetic acid, azido-, ethyl ester → ethyl 2-(4-cyano-1H-1,2,3-triazol-1-yl)acetate

HRID 651248Notes

Reaction equation

HRID 651248 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]>O>[CH2:8]([O:7][C:5](=[O:6])[CH2:4][N:1]1[CH:14]=[C:11]([C:12]#[N:13])[N:3]=[N:2]1)[CH3:9]

Participants

4

Reactant 2

HCID 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

Conditions

Temperature
80 °C

Procedure

A mixture of ethyl 2-azidoacetate (1.29 g) and 2-chloroacrylonitrile (1.75 g) in water (10 ml) is stirred at about 80° C. for 16 hours. After cooling, the product is extracted with dichloromethane and the concentrated extract is purified by means of column chromatography on silica gel 60 (6 g; eluent toluenelethyl acetate=4:1). The purified product (yield 1.21 g; 67% of theory) of m.p. 47-48° C. (recrystallization from toluene/hexane) is obtained after concentrating the eluate and drying.

Workup

  1. temperatureAfter cooling
  2. extractionthe product is extracted with dichloromethane
  3. extractionthe concentrated extract
  4. customis purified by means of column chromatography on silica gel 60 (6 g; eluent toluenelethyl acetate=4:1)
  5. customThe purified product (yield 1.21 g; 67% of theory) of m.p. 47-48° C. (recrystallization from toluene/hexane)
  6. customis obtained
  7. concentrationafter concentrating the eluate and
  8. customdrying

Sources & evidence

ORD record
ord-bad92f970fae4fd68d2e6c1269ce3453
Source dataset
uspto-grants-2001_08
Patent number
US06277999B1

Reaction notes

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