Triethylamine hydrochloride → HCID 178506136, compound

HRID 1924428Notes

Reaction equation

HRID 1924428 reaction equation
[F:1][C:2]([F:12])([F:11])[C:3]1[CH:10]=[CH:9][CH:8]=[CH:7][C:4]=1[C:5]#[N:6].[N-:13]=[N+:14]=[N-:15].[Na+].Cl.C(N(CC)CC)C>C1(C)C=CC=CC=1>[F:1][C:2]([F:11])([F:12])[C:3]1[CH:10]=[CH:9][CH:8]=[CH:7][C:4]=1[C:5]1[NH:15][N:14]=[N:13][N:6]=1

Participants

5

Reactant 3

HCID 11130Triethylamine hydrochlorideHCID 33557Sodium AzideHCID 679722-(Trifluoromethyl)benzonitrile

Product 1

HCID 178506136HCID 178506136, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
110 °C

Procedure

A vigorously stirred suspension of 2-(trifluoromethyl)benzonitrile (2-A) (6.34 g, 37 mmol), sodium azide (4.81 g, 74 mmol) and triethylamine hydrochloride (10.19 g, 74 mmol) in toluene (70 mL) was heated at 110° C. for 48 h. The mixture was cooled and extracted twice with water. The combined extracts were washed with hexane and brought to pH about 1 with concentrated HCl. The precipitate which formed was filtered, washed with water and dried to give 5-[2-(trifluoromethyl)phenyl]-1H-tetrazole (2-B).

Workup

  1. temperatureThe mixture was cooled
  2. extractionextracted twice with water
  3. washThe combined extracts were washed with hexane
  4. customThe precipitate which formed
  5. filtrationwas filtered
  6. washwashed with water
  7. customdried

Sources & evidence

ORD record
ord-d4a4c10ce4dc490b844a1ab037243215
Source dataset
uspto-grants-2012_05
Patent number
US08178546B2

Reaction notes

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