Potassium Hydroxide → 2-(2,6-dichloro-4-trifluoromethylphenyl)-4-[(4,5-dicyano-1H-imidazol-2-ylamino)-methyl]-2H-1,2,3-triazole

HRID 1031159Notes

Reaction equation

HRID 1031159 reaction equation
C([BH3-])#N.[Na+].[Cl:5][C:6]1[CH:11]=[C:10]([C:12]([F:15])([F:14])[F:13])[CH:9]=[C:8]([Cl:16])[C:7]=1[N:17]1[N:21]=[C:20]([CH:22]=O)[CH:19]=[N:18]1.[OH-].[K+].[NH2:26][C:27]1[NH:28][C:29]([C:34]#[N:35])=[C:30]([C:32]#[N:33])[N:31]=1>CO>[Cl:5][C:6]1[CH:11]=[C:10]([C:12]([F:15])([F:14])[F:13])[CH:9]=[C:8]([Cl:16])[C:7]=1[N:17]1[N:21]=[C:20]([CH2:22][NH:26][C:27]2[NH:28][C:29]([C:34]#[N:35])=[C:30]([C:32]#[N:33])[N:31]=2)[CH:19]=[N:18]1

Participants

6

Reactant 4

HCID 14797Potassium HydroxideHCID 1704461H-Imidazole-4,5-dicarbonitrile, 2-amino-HCID 5003444Sodium cyanoborohydrideHCID 197783082-(2,6-Dichloro-4-trifluoromethylphenyl)-1,2,3-triazole-4-carboxaldehyde

Product 1

HCID 197783732-(2,6-dichloro-4-trifluoromethylphenyl)-4-[(4,5-dicyano-1H-imidazol-2-ylamino)-methyl]-2H-1,2,3-triazole

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium cyanoborohydride (0.05 g) was added to a solution of 2-(2,6-dichloro-4-trifluoromethylphenyl)-1,2,3-triazole-4-carboxaldehyde (0.3 g), potassium hydroxide (0.04 g) and 2-amino-4,5-dicyanoimidazole (0.3 g) in methanol (20 ml). After 20 hours at room temperature, the solvent was evaporated under reduced pressure and the residue purified by silica gel chromatography to give 2-(2,6-dichloro-4-trifluoromethylphenyl)-4-[(4,5-dicyano-1H-imidazol-2-ylamino)-methyl]-2H-1,2,3-triazole, m.p. 213°-215°. (Compound 25)

Workup

  1. customthe solvent was evaporated under reduced pressure
  2. customthe residue purified by silica gel chromatography

Sources & evidence

ORD record
ord-3bd80c9a343f45a7afd65a723c0c6022
Source dataset
uspto-grants-1992_04
Patent number
US05109012

Reaction notes

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