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]>CCCCCCC>[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) and 2-chloroacrylonitrile (26.6 g) is stirred at about 80° C. for 24 hours. n-Heptane (125 ml) is allowed to run in, and unreacted 2-chloroacrylonitrile and 2,6-difluorobenzyl azide as well as n-hepiarie are distilled off (distillate 50 ml) by raising the external temperature to about 130° C. 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: 31.55 g=71.6% (beige powder).
Workup
- distillationare distilled off (distillate 50 ml)
- temperatureby raising the external temperature to about 130° C
- temperatureThe mixture is cooled to about 20° C.
- stirringthe suspension is stirred at about 20° C. for 1 hour
- customThe product is isolated by filtration
- washwashed with n-heptane (100 ml)
- customThe product is dried in vacuo at about 60° C
Sources & evidence
- ORD record
- ord-097cb92542f64ff09dda0bbaf20615a7
- Source dataset
- uspto-grants-2000_12
- Patent number
- US06156907
Reaction notes
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