1-Fluoro-2-nitrobenzene → HCID 21093482, compound

HRID 1350522Notes

Reaction equation

HRID 1350522 reaction equation
[NH2:1][C:2]1[C:3]([C:10]#[N:11])=[N:4][N:5]([CH:7]([CH3:9])[CH3:8])[N:6]=1.F[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[N+:19]([O-:21])=[O:20].O.[OH-].[Li+]>CS(C)=O>[CH:7]([N:5]1[N:4]=[C:3]([C:10]#[N:11])[C:2]([NH:1][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[N+:19]([O-:21])=[O:20])=[N:6]1)([CH3:9])[CH3:8]

Participants

5

Reactant 3

HCID 738951-Fluoro-2-nitrobenzeneHCID 168937Lithium hydroxide, monohydrateHCID 21093531HCID 21093531, compound

Product 1

HCID 21093482HCID 21093482, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Combine 5-amino-2-isopropyl-2H-1,2,3-triazole-4-carbonitrile (44.2 g, 0.292 mol) and 2-fluoronitrobenzene (41.25 g, 0.292 mol) in dimethylsulphoxide (590 ml) and stir in the presence of lithium hydroxide monohydrate (24.56 g;0.584 mol) for eighteen hours at 55° C. Pour the reaction mixture onto ice-water, stir for one hour, filter and wash the filter pad well with water to leave a yellow crystalline solid to give 2-isopropyl-5-(2-nitroanilino)-2H-1,2,3-triazole4-carbonitrile (73.7 g, 93% yield): 1HNMR/c: 1.6 ppm (d, 6H), 4.8 ppm (m, 1H), 7.05 ppm (tr, 1H), 7.64 ppm (tr, 1H), 8.2 ppm (dd, 1H), 8.28 ppm (dd, 1H), 10.25 ppm (s, 1H).

Workup

  1. additionPour the reaction mixture onto ice-water
  2. filtrationfilter
  3. washwash the filter pad well with water
  4. customto leave a yellow crystalline solid

Sources & evidence

ORD record
ord-dfc1c616a4694f90b506508f1d2d54be
Source dataset
uspto-grants-2007_05
Patent number
US07214673B2

Reaction notes

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