2-Chloroacrylonitrile → 4-Cyano-1-(4-cyanobenzyl)-1H-1,2,3-triazole

HRID 651246

Reaction equation

HRID 651246 reaction equation
[C:1]([C:3]1[CH:12]=[CH:11][C:6]([CH2:7][N:8]=[N+:9]=[N-:10])=[CH:5][CH:4]=1)#[N:2].Cl[C:14](=[CH2:17])[C:15]#[N:16]>O>[C:15]([C:14]1[N:10]=[N:9][N:8]([CH2:7][C:6]2[CH:5]=[CH:4][C:3]([C:1]#[N:2])=[CH:12][CH:11]=2)[CH:17]=1)#[N:16]

Participants

4

Reactant 2

HCID 701982-ChloroacrylonitrileHCID 110736914-(Azidomethyl)benzonitrile

Product 1

HCID 217118034-Cyano-1-(4-cyanobenzyl)-1H-1,2,3-triazole

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 4-cyanobenzyl azide (0.8 g) and 2-chloroacrylonitrile (0.88 9) in water (5 ml) is stirred at about 80° C. for 20 hours. Excess 2-chloroacrylonitrile is distilled off in vacuo, the mixture is cooled to room temperature and the precipitated product is isolated by filtration and washed with water. The product (yield 0.92 g; 88% of theory) of m.p. 93.5-94° C. (recrystallization from ethyl acetate/toluene) is obtained after drying.

Workup

  1. distillationExcess 2-chloroacrylonitrile is distilled off in vacuo
  2. temperaturethe mixture is cooled to room temperature
  3. customthe precipitated product is isolated by filtration
  4. washwashed with water
  5. customThe product (yield 0.92 g; 88% of theory) of m.p. 93.5-94° C. (recrystallization from ethyl acetate/toluene)
  6. customis obtained
  7. customafter drying

Sources & evidence

ORD record
ord-5b259ba147ce4c3fa3a12c8236554aa0
Source dataset
uspto-grants-2001_08
Patent number
US06277999B1

Linked notes

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