1H-1,2,4-Triazole → 5-Chloro-2-(1H-1,2,4-triazol-1-YL)benzonitrile

HRID 397518

Reaction equation

Cl[C:2]1[CH:9]=[CH:8][C:7]([Cl:10])=[CH:6][C:3]=1[C:4]#[N:5].C(=O)([O-])[O-].[Cs+].[Cs+].[NH:17]1[CH:21]=[N:20][CH:19]=[N:18]1>CN(C=O)C.O>[Cl:10][C:7]1[CH:8]=[CH:9][C:2]([N:17]2[CH:21]=[N:20][CH:19]=[N:18]2)=[C:3]([CH:6]=1)[C:4]#[N:5]

Participants

Conditions

Temperature: 85 °C

Procedure

To a solution of 2,5-dichlorobenzonitrile (10 g, 58.1 mmol) in DMF (100 ml) is added cesium carbonate (22.7 g, 69.8 mmol) and 1,2,4-triazole (4.8 g, 69.8 mmol) and the reaction mixture is stirred at 65° C. for 5.5 h, at 75° C. for 16 h, at 85° C. for 7 h. More 1,2,4-triazole (5 g) is added and the reaction mixture is stirred at 85° C. for 18 h and at 100° C. for 4 h. After cooling to room temperature, the mixture is diluted with water and extracted with EtOAc 3 times. The combined organic layer is washed with aqueous LiCl, dried on sodium sulfate, concentrated in vacuo to give 5-Chloro-2-[1,2,4]triazol-1-yl-benzonitrile as a white solid which is used in the next step without further purification.

Workup

stirringthe reaction mixture is stirred at 85° C. for 18 h and at 100° C. for 4 h
temperatureAfter cooling to room temperature
extractionextracted with EtOAc 3 times
washThe combined organic layer is washed with aqueous LiCl
customdried on sodium sulfate
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-4eec846f019147878c9190737f6e39cb
Source dataset: uspto-grants-2003_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06610701B2

Linked notes

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