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

HRID 1274504Notes

Reaction equation

HRID 1274504 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>[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

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: toluene/ethyl 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: toluene/ethyl 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-7274074ca09d4afe91718cc1127c8d38
Source dataset
uspto-grants-2000_12
Patent number
US06156907

Reaction notes

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