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 for 24 hours at about 80°C. By increasing the external temperature to about 130°C., excess 2-chloroacrylonitrile is distilled off. The semisolid mixture is cooled to about 40°C., cyclohexane (50 ml) is added to the suspension and the mixture is brought to about 20°C.and stirred for about 2 hours. The product is isolated by filtration and 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 at about 60°C. in vacuo. Yield: 38.04 g =86%.
Workup
- temperatureBy increasing the external temperature to about 130°C.
- distillationexcess 2-chloroacrylonitrile is distilled off
- temperatureThe semisolid mixture is cooled to about 40°C.
- additioncyclohexane (50 ml) is added to the suspension
- customis brought to about 20°C
- stirringand stirred 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 at about 60°C. in vacuo
Sources & evidence
- ORD record
- ord-94cf4427043e41f7a0bd38fe6309e94b
- Source dataset
- uspto-grants-2010_07
- Patent number
- US07750028B2
Reaction notes
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