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

HRID 651243Notes

Reaction equation

HRID 651243 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]>C1(C)C=CC=CC=1>[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-Chloroacrylonitrile2×HCID 108883232-(Azidomethyl)-1,3-difluorobenzene2×

Product 1

HCID 110422394-Cyano-1-(2,6-difluorobenzyl)-1H-1,2,3-triazole

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Conditions

Temperature
80 °C

Procedure

A mixture of 2,6-difluorobenzyl azide (34.2 g), 2-chloroacrylonitrile (26.6 g) and toluene (125 ml) is stirred at about 80° C. for 24 hours. Unreacted 2-chloroacrylonitrile and 2,6-difluorobenzyl azide as well as toluene are distilled off (distillate 100 ml) by raising the external temperature to about 130° C. After cooling to 80° C., n-heptane (100 ml) is allowed to run in. The mixture is cooled to about 20° C. and the suspension is stirred at about 20° C. for 1 hour. The product is isolated by filtration and washed with n-heptane (100 ml). The product is dried in vacuo at about 60° C. Yield: 22.31 g=50.7% (beige powder).

Workup

  1. distillationare distilled off (distillate 100 ml)
  2. temperatureby raising the external temperature to about 130° C
  3. temperatureAfter cooling to 80° C.
  4. temperatureThe mixture is cooled to about 20° C.
  5. stirringthe suspension is stirred at about 20° C. for 1 hour
  6. customThe product is isolated by filtration
  7. washwashed with n-heptane (100 ml)
  8. customThe product is dried in vacuo at about 60° C

Sources & evidence

ORD record
ord-684d2c6872fb4fe3bab10916a3888e03
Source dataset
uspto-grants-2001_08
Patent number
US06277999B1

Reaction notes

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