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

HRID 1960021Notes

Reaction equation

HRID 1960021 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 (1.2 g, 64 mmol) is added portionwise slowly to an EtOH (100 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 extracted with EtOAc. The combined organic layer is washed with brine, dried over magnesium sulfate, filtered and concentrated The residue is purified by silica gel column chromatography chromatography to give N-[3,5-bis(trifluoromethyl)benzyl]-N-(2-methyl-2H-tetrazol-5-yl)amine as a white crystalline solid.

Workup

  1. extractionthe mixture is extracted with EtOAc
  2. washThe combined organic layer is washed with brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated The residue
  6. customis purified by silica gel column chromatography chromatography

Sources & evidence

ORD record
ord-e37fbdf5fd964920a7fcff2ea9820eab
Source dataset
uspto-grants-2013_04
Patent number
US08410275B2

Reaction notes

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