3,5-Bis(trifluoromethyl)benzaldehyde → 5-[N-(3',5'-Bistrifluoromethylbenzyl)amino]-2-methyltetrazole

HRID 1157740

Reaction equation

HRID 1157740 reaction equation
[F:1][C:2]([F:16])([F:15])[C:3]1[CH:4]=[C:5]([CH:8]=[C:9]([C:11]([F:14])([F:13])[F:12])[CH:10]=1)[CH:6]=O.[NH2:17][C:18]1[N:19]=[N:20][N:21]([CH3:23])[N:22]=1>C1(C)C=CC=CC=1>[F:1][C:2]([F:16])([F:15])[C:3]1[CH:4]=[C:5]([CH:8]=[C:9]([C:11]([F:14])([F:13])[F:12])[CH:10]=1)[CH2:6][NH:17][C:18]1[N:19]=[N:20][N:21]([CH3:23])[N:22]=1

Participants

4

Reactant 2

HCID 1362473,5-Bis(trifluoromethyl)benzaldehydeHCID 1386772-methyl-2H-1,2,3,4-tetrazol-5-amine

Product 1

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

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution (70 ml) of 3,5-bis(trifluoromethyl)benzaldehyde (6.71 g) and 5-amino-2-methyltetrazole (3.30 g) in toluene was heated under reflux for 4 hr. The reaction solution was concentrated and the obtained residue was dissolved in ethanol (70 ml), and sodium borohydride (2.10 g) was added with stirring at room temperature. The reaction solution was stirred at room temperature for 30 min, and saturated aqueous ammonium chloride was added. The mixture was extracted with ethyl acetate. The extract was washed successively with water and saturated brine. The organic layer was dried over sodium sulfate and sodium sulfate was filtered off. The filtrate was concentrated and the obtained residue was recrystallized from isopropanol-water (3:7, 50 ml) to give the title compound.

Workup

  1. temperatureunder reflux for 4 hr
  2. concentrationThe reaction solution was concentrated
  3. dissolutionthe obtained residue was dissolved in ethanol (70 ml)
  4. additionsodium borohydride (2.10 g) was added
  5. stirringThe reaction solution was stirred at room temperature for 30 min
  6. additionsaturated aqueous ammonium chloride was added
  7. extractionThe mixture was extracted with ethyl acetate
  8. washThe extract was washed successively with water and saturated brine
  9. dry with materialThe organic layer was dried over sodium sulfate and sodium sulfate
  10. filtrationwas filtered off
  11. concentrationThe filtrate was concentrated
  12. customthe obtained residue was recrystallized from isopropanol-water (3:7, 50 ml)

Sources & evidence

ORD record
ord-fb6eab3294a14c70b64159915537d9c9
Source dataset
uspto-grants-2010_10
Patent number
US07807701B2

Linked notes

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