Sodium hydride → 1-Phenyl-5-(4-cyano-2-trifluoromethylanilino)tetrazole

HRID 1602073Notes

Reaction equation

HRID 1602073 reaction equation
[NH2:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][C:3]=1[C:10]([F:13])([F:12])[F:11].[H-].[Na+].[H][H].Cl[C:19]1[N:23]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[N:22]=[N:21][N:20]=1>O1CCCC1>[C:24]1([N:23]2[C:19]([NH:1][C:2]3[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][C:3]=3[C:10]([F:11])([F:12])[F:13])=[N:20][N:21]=[N:22]2)[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 842621H-Tetrazole, 5-chloro-1-phenyl-HCID 27794884-Amino-3-(trifluoromethyl)benzonitrileHCID 178418361HCID 178418361, compound

Product 1

HCID 110457501-Phenyl-5-(4-cyano-2-trifluoromethylanilino)tetrazoleYield 93.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4-Amino-3-trifluoromethyl-benzonitrile (0.9 g) was added to a tetrahydrofuran solution (25 ml) of sodium hydride (0.5 g; 60% in oil) at room temperature. The mixture was stirred at room temperature for about 10 minutes until the generation of hydrogen gas was ceased. Then, 5-chloro-1-phenyltetrazole (0.9 g) was added thereto and the mixture was stirred for 2 hours. The reaction solution was poured into 100 ml of ice water and the organic layer was distilled off under reduced pressure. Activated carbon was added to the aqueous layer and the aqueous layer was filtered. Then, the pH of the filtrate was adjusted to 2-3 with concentrated hydrochloric acid. The precipitated crystals were collated by filtration and washed with water and n-hexane to obtain 1-phenyl-5-(4-cyano-2-trifluoromethylanilino)tetrazole (1.5 g).

Workup

  1. distillationthe organic layer was distilled off under reduced pressure
  2. additionActivated carbon was added to the aqueous layer
  3. filtrationthe aqueous layer was filtered
  4. filtrationThe precipitated crystals were collated by filtration
  5. washwashed with water and n-hexane

Sources & evidence

ORD record
ord-a4a1e507048e4eda9ea58d08e5e9f0e0
Source dataset
uspto-grants-1999_11
Patent number
US05981438

Reaction notes

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