Dimethyl Sulfoxide → 2-Nitro-5-(1,2,4-triazol-1-yl)benzonitrile

HRID 618684Notes

Reaction equation

HRID 618684 reaction equation
F[C:2]1[CH:3]=[CH:4][C:5]([N+:10]([O-:12])=[O:11])=[C:6]([CH:9]=1)[C:7]#[N:8].[NH:13]1[CH:17]=[N:16][CH:15]=[N:14]1.C(N(CC)CC)C.CS(C)=O>O>[N+:10]([C:5]1[CH:4]=[CH:3][C:2]([N:13]2[CH:17]=[N:16][CH:15]=[N:14]2)=[CH:9][C:6]=1[C:7]#[N:8])([O-:12])=[O:11]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 92571H-1,2,4-TriazoleHCID 37564675-Fluoro-2-nitrobenzonitrile

Product 1

HCID 218478142-Nitro-5-(1,2,4-triazol-1-yl)benzonitrileYield 48.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
85 °C

Procedure

A mixture of 5-fluoro-2-nitrobenzonitrile (3 g), 1,2,4-triazole (4.92 g), triethylamine (9.9 ml) and DMSO (50 ml) was stirred and heated to 85° C. for 16 hours. The mixture was cooled to ambient temperature and water was added. The precipitate was isolated and dried to give 2-nitro-5-(1,2,4-triazol-1-yl)benzonitrile (1.9 g) which was used without further purification.

Workup

  1. temperatureThe mixture was cooled to ambient temperature
  2. customThe precipitate was isolated
  3. customdried

Sources & evidence

ORD record
ord-349c67f423c24cd69dd63425a6f5d688
Source dataset
uspto-grants-1999_09
Patent number
US05955464

Reaction notes

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