2-Chloroacrylonitrile → 4-Cyano-1-(2,6-difluorobenzyl)-1H-1,2,3-triazole

HRID 1274494Notes

Reaction equation

HRID 1274494 reaction equation
[F:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]([F:12])[C:3]=1[CH2:4][N:5]=[N+:6]=[N-:7].Cl[C:14](=[CH2:17])[C:15]#[N:16]>O>[C:15]([C:14]1[N:7]=[N:6][N:5]([CH2:4][C:3]2[C:2]([F:1])=[CH:11][CH:10]=[CH:9][C:8]=2[F:12])[CH:17]=1)#[N:16]

Participants

4

Reactant 2

HCID 701982-ChloroacrylonitrileHCID 108883232-(Azidomethyl)-1,3-difluorobenzene

Product 1

HCID 110422394-Cyano-1-(2,6-difluorobenzyl)-1H-1,2,3-triazoleYield 87.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 2,6-difluorobenzyl azide (6.75 g), 2-chloroacrylonitrile (7.0 g) and water (20 ml) is stirred at about 80° C. for 12 hours. Excess 2-chloroacrylonitrile is distilled off by raising the external temperature to about 120° C. The mixture is cooled to about 20° C. and the crystallized product is isolated by filtration and washed with water. The moist product is dried in vacuo at about 60° C. Yield: 8.17 g=93%. For purification, the product (8.17 g) is dissolved in toluene (40 ml) at 80° C. and treated with bleaching earth (0.24 g), and the mixture is filtered hot. The filtrate is concentrated to about 20 ml and the resulting crystal magma is stirred at 0° C. for 1 hour. After filtering, washing with toluene and drying, a white product (7.72 g) of m.p. 115.5-116.5° C. is obtained.

Workup

  1. distillationExcess 2-chloroacrylonitrile is distilled off
  2. temperatureby raising the external temperature to about 120° C
  3. temperatureThe mixture is cooled to about 20° C.
  4. customthe crystallized product is isolated by filtration
  5. washwashed with water
  6. customThe moist product is dried in vacuo at about 60° C
  7. customFor purification
  8. dissolutionthe product (8.17 g) is dissolved in toluene (40 ml) at 80° C.
  9. additiontreated with bleaching earth (0.24 g)
  10. filtrationthe mixture is filtered hot
  11. concentrationThe filtrate is concentrated to about 20 ml
  12. stirringthe resulting crystal magma is stirred at 0° C. for 1 hour
  13. filtrationAfter filtering
  14. washwashing with toluene
  15. customdrying

Sources & evidence

ORD record
ord-0c7261a06db34e5eb6a2cedfc58564a5
Source dataset
uspto-grants-2000_12
Patent number
US06156907

Reaction notes

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