Triethylamine hydrochloride → HCID 15470707, compound

HRID 1180715Notes

Reaction equation

HRID 1180715 reaction equation
[Cl: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>[Cl: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 10243436HCID 10243436, compound

Product 1

HCID 15470707HCID 15470707, compoundYield 92.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Three grams (12.4 mmol) of N-(4-chlorophenyl)-2,2,2-trifluoroacetimidoyl chloride obtained in Example 11, 1.46 g (22.3 mmol) of sodium azide, 0.85 g (6.20 mmol) of triethylamine hydrochloride, and 30 ml of toluene were introduced into a 100 ml flask and reacted at 80° C. for 24.5 hours. After the reaction, the reaction solution was cooled to room temperature and washed with water (20 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 2.84 g of 1-(4-chlorophenyl)-5-(trifluoromethyl)-1H-tetrazole as a pale yellow oil (yield: 92.2%).

Workup

  1. customreacted at 80° C. for 24.5 hours
  2. customAfter the reaction
  3. washwashed with water (20 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-74a27d00f644465f9231f0dbd289ab80
Source dataset
uspto-grants-2007_10
Patent number
US07282609B2

Reaction notes

Loading…