1H-1,2,4-Triazole → 4-(1,2,4-Triazol-1-ylmethyl)benzonitrile

HRID 1111161

Reaction equation

HRID 1111161 reaction equation
Br[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]#[N:10])=[CH:5][CH:4]=1.[NH:11]1[CH:15]=[N:14][CH:13]=[N:12]1>C(Cl)(Cl)Cl.C(#N)C>[CH:8]1[C:3]([CH2:2][N:11]2[N:12]=[CH:13][N:14]=[CH:15]2)=[CH:4][CH:5]=[C:6]([C:9]#[N:10])[CH:7]=1

Participants

5

Reactant 2

HCID 92571H-1,2,4-TriazoleHCID 869964-(Bromomethyl)benzonitrile

Product 1

HCID 75376164-(1,2,4-Triazol-1-ylmethyl)benzonitrile

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6342AcetonitrileSolvent

Procedure

A solution containing alpha-bromo-4-tolunitrile (19.6 g) and 1,2,4-triazole (30.5 g) in a mixture of chloroform (250 mL) and acetonitrile (50 mL) is stirred at reflux for 15 hours. The solution is cooled and washed with 3% aqueous sodium bicarbonate (200 mL) and the organic solution is then dried (MgSO4) and evaporated. The residue is chromatographed on silica gel (300 g). Elution with chloroform/isopropanol (10:1) affords 4-[1-(1,2,4-triazolyl)methyl]-benzontrile, m.p. 77°-79°, which forms a hydrochloride salt, m.p. 200°-205°, when its solution in ethyl acetate is treated with ethereal HCl.

Workup

  1. temperatureat reflux for 15 hours
  2. temperatureThe solution is cooled
  3. washwashed with 3% aqueous sodium bicarbonate (200 mL)
  4. dry with materialthe organic solution is then dried (MgSO4)
  5. customevaporated
  6. customThe residue is chromatographed on silica gel (300 g)
  7. washElution with chloroform/isopropanol (10:1)

Sources & evidence

ORD record
ord-75608f9dafaa46ef8d42a7355ab039bb
Source dataset
uspto-grants-1990_12
Patent number
US04978672

Linked notes

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