2-Chloroacrylonitrile → 4-Cyano-1-(2,6-difluorobenzyl)-1H-1,2,3-triazole
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
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 80 °C
Procedure
A mixture of 2.6-difluorobenzyl azide (34.2 g), 2-chloroacrylonitrile (17.73 g) and water (125 ml) is stirred at about 80° C. for 24 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 (50 ml). The moist product is mixed with water (100 ml), the suspension is filtered and the product is washed with water (50 ml) and dried in vacuo at about 60° C. Yield: 38.04 g=86%.
Workup
- distillationExcess 2-chloroacrylonitrile is distilled off
- temperatureby raising the external temperature to about 130° C
- temperatureThe semi-solid mixture is cooled to about 40° C.
- additionthe suspension is treated with cyclohexane (50 ml)
- custombrought to about 20° C.
- stirringstirred for about 2 hours
- customThe product is isolated by filtration
- washwashed with cyclohexane (75 ml)
- additionThe moist product is mixed with water (100 ml)
- filtrationthe suspension is filtered
- washthe product is washed with water (50 ml)
- customdried in vacuo at about 60° C
Sources & evidence
- ORD record
- ord-66074350972d4efa86560cd93bd90c15
- Source dataset
- uspto-grants-2001_08
- Patent number
- US06277999B1
Reaction notes
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