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

HRID 651237Notes

Reaction equation

HRID 651237 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-triazole

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 2,6-difluorobenzyl azide (34.2 g), 2-chloroacrylonitrile (17.73 9) and water (125 ml) is stirred at about 80° C. for 48 hours. Excess 2-chloroacrylonitrile is distilled off by raising the external temperature to about 130° C. The semi-solid mixture is cooled to about 40° C. and the suspension is treated with cyclohexane (50 ml), brought to about 20° C. and stirred for about 2 hours. The product is isolated by filtration, washed with cyclohexane (75 ml) and then with water and dried in vacuo at about 60° C.

Workup

  1. distillationExcess 2-chloroacrylonitrile is distilled off
  2. temperatureby raising the external temperature to about 130° C
  3. temperatureThe semi-solid mixture is cooled to about 40° C.
  4. additionthe suspension is treated with cyclohexane (50 ml)
  5. custombrought to about 20° C.
  6. stirringstirred for about 2 hours
  7. customThe product is isolated by filtration
  8. washwashed with cyclohexane (75 ml)
  9. dry with materialwith water and dried in vacuo at about 60° C.

Sources & evidence

ORD record
ord-cf69b06065b54234b8fefb8cf06c0bc0
Source dataset
uspto-grants-2001_08
Patent number
US06277999B1

Reaction notes

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