Triethylamine hydrochloride → HCID 14663405, compound

HRID 1180707Notes

Reaction equation

HRID 1180707 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]=[C:9](Cl)[C:10]([F:13])([F:12])[F:11])=[CH:4][CH:3]=1.[N-:15]=[N+:16]=[N-:17].[Na+].Cl.C(N(CC)CC)C>C1(C)C=CC=CC=1>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:9]([C:10]([F:13])([F:12])[F:11])=[N:17][N:16]=[N:15]2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 11130Triethylamine hydrochlorideHCID 33557Sodium AzideHCID 11775698HCID 11775698, compound

Product 1

HCID 14663405HCID 14663405, compoundYield 97.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Five grams (22.6 mmol) of N-(4-methylphenyl)-2,2,2-trifluoroacetimidoyl chloride obtained in Example 3, 2.68 g (40.7 mmol) of sodium azide, 1.57 g (11.3 mmol) of triethylamine hydrochloride, and 40 ml of toluene were introduced into a 100 ml flask and reacted at 80° C. for 23 hours. After the reaction, the reaction solution was cooled to room temperature and washed with water (30 ml×3). 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 5.01 g of 1-(4-methylphenyl)-5-(trifluoromethyl)-1H-tetrazole as a pale yellow oil (yield: 97.3%).

Workup

  1. customreacted at 80° C. for 23 hours
  2. customAfter the reaction
  3. washwashed with water (30 ml×3)
  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-ed43e9a7aad44182906c13ab567d2e0f
Source dataset
uspto-grants-2007_10
Patent number
US07282609B2

Reaction notes

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