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

HRID 651244Notes

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]>CN(C)C=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

Conditions

Temperature: 80 °C

Procedure

A mixture of 2,6-difluorbenzyl azide (34.2 g), 2-chloroacrylonitrile (26.6 g) and N,N-dimethylformamide (125 ml) is stirred at about 80° C. for 24 hours. Unreacted 2-chloroacrylonitrile and 2,6-difluorobenzyl azide as well as N,N-dimethylformamide are distilled off (distillate 100 ml) by raising the external temperature to about 130° C. and gradually evacuating to about 100 mbar. After cooling to 100° C., water (100 ml) is allowed to run in. The crystallization of the product is initiated by seeding the brown emulsion. The mixture is cooled to about 20° C. and the suspension is stirred at about 20° C. for 30 minutes. The product is isolated by filtration and washed with water (100 ml). The product is dried in vacuo at about 60° C. Yield: 34.40 g=78.1% (beige crystals).

Workup

distillationare distilled off (distillate 100 ml)
temperatureby raising the external temperature to about 130° C.
customgradually evacuating to about 100 mbar
temperatureAfter cooling to 100° C.
customThe crystallization of the product
temperatureThe mixture is cooled to about 20° C.
stirringthe suspension is stirred at about 20° C. for 30 minutes
customThe product is isolated by filtration
washwashed with water (100 ml)
customThe product is dried in vacuo at about 60° C

Sources & evidence

ORD record: ord-73c93e941564404ab1c53ace4db5a0df
Source dataset: uspto-grants-2001_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06277999B1

Reaction notes

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