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

HRID 1274502Notes

Reaction equation

HRID 1274502 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 g) 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-350d74dde51f4ae7b3a70bbb05db9e6b
Source dataset
uspto-grants-2000_12
Patent number
US06156907

Reaction notes

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