Ethanol → 5-[N-(3',5'-Bistrifluoromethylbenzyl)amino]-2-methyltetrazole

HRID 1518063Notes

Reaction equation

HRID 1518063 reaction equation
[BH4-].[Na+].CCO.[CH3:6][N:7]1[N:11]=[N:10][C:9]([N:12]=[CH:13][C:14]2[CH:19]=[C:18]([C:20]([F:23])([F:22])[F:21])[CH:17]=[C:16]([C:24]([F:27])([F:26])[F:25])[CH:15]=2)=[N:8]1.[NH4+].[Cl-]>O>[F:23][C:20]([F:21])([F:22])[C:18]1[CH:19]=[C:14]([CH:15]=[C:16]([C:24]([F:26])([F:27])[F:25])[CH:17]=1)[CH2:13][NH:12][C:9]1[N:10]=[N:11][N:7]([CH3:6])[N:8]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 25517Ammonium ChlorideHCID 4311764Sodium borohydrideHCID 766457252-methyl-N-[3,5-bis(trifluoromethyl)phenylmethylene]-2H-tetrazole-5-amine

Product 1

HCID 230732215-[N-(3',5'-Bistrifluoromethylbenzyl)amino]-2-methyltetrazole

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

NaBH4 (8.2 g, 0.22 mol) is added portionwise slowly to EtOH (700 mL) solution of crude 2-methyl-N-[3,5-bis(trifluoromethyl)phenylmethylene]-2H-tetrazole-5-amine at 0° C., and the mixture is stirred at room temperature for 1 hour. After addition of sat. NH4Cl aq. and water at 0° C., the mixture is concentrated to remove 300 mL of EtOH and extracted with CH2Cl2 (300 mL×4 times). The combined organic layer is washed with brine, dried over magnesium sulfate, filtered and concentrated The residue is purified by silica gel column chromatography to give N-[3,5-bis(trifluoromethyl)benzyl]-N-(2-methyl-2H-tetrazol-5-yl)amine as a white crystalline solid.

Workup

  1. concentrationthe mixture is concentrated
  2. customto remove 300 mL of EtOH
  3. extractionextracted with CH2Cl2 (300 mL×4 times)
  4. washThe combined organic layer is washed with brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated The residue
  8. customis purified by silica gel column chromatography

Sources & evidence

ORD record
ord-7678474de967423bbd0872b85cfd1cbc
Source dataset
uspto-grants-2012_07
Patent number
US08232403B2

Reaction notes

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