Dimethylformamide → 2-Methoxy-6-(1,2,4-triazol-1-yl)-benzonitrile

HRID 1533835Notes

Reaction equation

HRID 1533835 reaction equation
[CH3:1][O:2][C:3]1[CH:10]=[CH:9][CH:8]=[C:7](F)[C:4]=1[C:5]#[N:6].N1C=[C-:15][N:14]=[N:13]1.[Na+].[CH3:18][N:19](C)C=O>>[CH3:1][O:2][C:3]1[CH:10]=[CH:9][CH:8]=[C:7]([N:14]2[CH:15]=[N:19][CH:18]=[N:13]2)[C:4]=1[C:5]#[N:6]

Participants

4

Reactant 3

HCID 6228Dimethylformamide2×HCID 5231012-Fluoro-6-methoxybenzonitrileHCID 129663835Sodium triazolide

Product 1

HCID 197799332-Methoxy-6-(1,2,4-triazol-1-yl)-benzonitrile

Conditions

Temperature
0 °C

Procedure

A solution of 30.2 g (0.20 mol) of 2-methoxy-6-fluorobenzonitrile [preparation: J. Heterocycl. Chem. 25 (1988), 1173]in 50 ml of N,N-dimethylformamide is added dropwise at 45°-50° C., under nitrogen, to a solution of 0.21 mol of sodium triazolide (prepared from equimolar amounts of triazol and sodium hydride) in 100 ml of N,N-dimethylformamide, and the mixture is stirred for 2 h at 0° C. After the solvent has been evaporated under reduced pressure, the residue is stirred with 200 ml of ice water, the pH is brought to 6 with a little glacial acetic acid and the solid is filtered off under suction and dried. After the addition of a little ether, 35 g of the product of melting point 169°-171° C. (decomposition) are obtained.

Workup

  1. customAfter the solvent has been evaporated under reduced pressure
  2. stirringthe residue is stirred with 200 ml of ice water
  3. filtrationthe solid is filtered off under suction
  4. customdried
  5. additionAfter the addition of a little ether, 35 g of the product of melting point 169°-171° C. (decomposition)
  6. customare obtained

Sources & evidence

ORD record
ord-64c7b8a49f8549c799be7c03c0040576
Source dataset
uspto-grants-1992_02
Patent number
US05085686

Reaction notes

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