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

HRID 390739

Reaction equation

HRID 390739 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.[CH3:17][N:18]1[N:22]=[N:21][C:20]([NH2:23])=[N:19]1.C(O)C.[BH4-].[Na+]>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:23][C:20]1[N:21]=[N:22][N:18]([CH3:17])[N:19]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 1362473,5-Bis(trifluoromethyl)benzaldehydeHCID 1386772-methyl-2H-1,2,3,4-tetrazol-5-amineHCID 4311764Sodium borohydride

Product 1

HCID 230732215-[N-(3',5'-Bistrifluoromethylbenzyl)amino]-2-methyltetrazoleYield 87.6%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 3,5-bis(trifluoromethyl)benzaldehyde (4 g, 16.5 mmol), 2-methyl-2H-tetrazol-5-amine (1.96 g, 19.8 mmol) and molecular sieves (5-10 Å beads) in toluene (50 mL) was heated at reflux for 4 hours, after which time the solvent was removed. Ethanol (50 mL) and sodium borohydride (1.25 g, 33 mmol) were added. The resulting mixture was stirred at room temperature for 30 minutes and then partitioned between saturated NH4Cl (50 mL) and ethyl acetate (2×50 mL). The combined organic layers were washed with saturated NaCl (50 mL), dried (MgSO4), filtered and concentrated to yield the title compound as a white solid (4.7 g). 1H NMR (400 MHz, CDCl3) δ 4.2 (s, 3 H) 4.7 (s, 1 H) 4.7 (s, 1 H) 5.0 (t, J=6.0 Hz, 1 H) 7.8 (s, 1 H) 7.9 (s, 2 H). MS (ES+) Calc: 325.08, Found: 325.8 (M+1).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 4 hours
  3. customafter which time the solvent was removed
  4. custompartitioned between saturated NH4Cl (50 mL) and ethyl acetate (2×50 mL)
  5. washThe combined organic layers were washed with saturated NaCl (50 mL)
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-63ad3bc616ff479fa3780317a102f092
Source dataset
uspto-grants-2013_02
Patent number
US08383660B2

Linked notes

Loading…