Triethylamine hydrochloride → 1-(4-methoxyphenyl)-5-(trifluoromethyl)-1H-tetrazole

HRID 1180711Notes

Reaction equation

HRID 1180711 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]=[C:10](Cl)[C:11]([F:14])([F:13])[F:12])=[CH:5][CH:4]=1.[N-:16]=[N+:17]=[N-:18].[Na+].Cl.C(N(CC)CC)C>C1(C)C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[C:10]([C:11]([F:14])([F:13])[F:12])=[N:18][N:17]=[N:16]2)=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 11130Triethylamine hydrochlorideHCID 33557Sodium AzideHCID 104216822,2,2-Trifluoro-N-(4-methoxyphenyl)acetimidoyl Chloride

Product 1

HCID 111182621-(4-methoxyphenyl)-5-(trifluoromethyl)-1H-tetrazoleYield 98.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Five grams (21.0 mmol) of N-(4-methoxyphenyl)-2,2,2-trifluoroacetimidoyl chloride obtained in Example 7, 2.46 g (37.8 mmol) of sodium azide, 1.45 g (10.5 mmol) of triethylamine hydrochloride, and 40 ml of toluene were introduced into a 100 ml flask and reacted at 80° C. for 15 hours. After the reaction, the reaction solution was cooled to room temperature and washed with water (30 ml×2). The organic phase was dried over anhydrous magnesium sulfate for 1 hour, filtered, and then subjected to solvent removal by evaporation. The crude product thus obtained was purified by column chromatography (silica gel, ethyl acetate:hexane=3:7), resulting in 5.05 g of 1-(4-methoxyphenyl)-5-(trifluoromethyl)-1H-tetrazole as a pale yellow oil (yield: 98.3%).

Workup

  1. customreacted at 80° C. for 15 hours
  2. customAfter the reaction
  3. washwashed with water (30 ml×2)
  4. dry with materialThe organic phase was dried over anhydrous magnesium sulfate for 1 hour
  5. filtrationfiltered
  6. customsubjected to solvent removal by evaporation
  7. customThe crude product thus obtained
  8. customwas purified by column chromatography (silica gel, ethyl acetate:hexane=3:7)

Sources & evidence

ORD record
ord-56304b3f96ea47948933147b04bdbab5
Source dataset
uspto-grants-2007_10
Patent number
US07282609B2

Reaction notes

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