HCID 19818669, compound → HCID 19818674, compound

HRID 1607613Notes

Reaction equation

HRID 1607613 reaction equation
Br[CH:2]([CH3:15])[C:3]([C:5]1[CH:10]=[CH:9][C:8]([C:11]([F:14])([F:13])[F:12])=[CH:7][N:6]=1)=[O:4].[NH:16]1[CH:20]=[N:19][CH:18]=[N:17]1.[Na]>C(#N)C.C(OCC)(=O)C>[N:16]1([CH:2]([CH3:15])[C:3]([C:5]2[CH:10]=[CH:9][C:8]([C:11]([F:14])([F:13])[F:12])=[CH:7][N:6]=2)=[O:4])[CH:20]=[N:19][CH:18]=[N:17]1

Participants

5

Reactant 2

HCID 19818669HCID 19818669, compoundHCID 454898221h-1,2,4-Triazole sodium salt

Product 1

HCID 19818674HCID 19818674, compound

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-(2-bromopropionyl)-5-trifluoromethyl-pyridine (5.8 g.) in acetonitrile (65 ml.) was added sodium 1,2,4-triazole (2.0 g.) and the solution was stirred for 90 minutes. The acetonitrile was evaporated under reduced pressure and the residue was partitioned between ethyl acetate and water. The organic layer was separated and the aqueous layer was extracted with ethyl acetate. The combined organic layer was washed with water, dried over magnesium sulphate and concentrated to dryness under reduced pressure to give a yellow gum. Chromatography on silica, using petroleum ether (bp (60°-80°): ethyl acetate 60/40 v/v as eluent, gave 2-[2-(1,2,4-triazol-1-yl)propionyl]-5-trifluoromethylpyridine as a pale yellow oil. Nmr in deuteriochloroform: δ1.88 (3H, d); 6.62 (1H, q); 7.9 (1H, s); 8.14 (2H, m); 8.36 (1H, s); 8.94 (1H, d).

Workup

  1. customThe acetonitrile was evaporated under reduced pressure
  2. customthe residue was partitioned between ethyl acetate and water
  3. customThe organic layer was separated
  4. extractionthe aqueous layer was extracted with ethyl acetate
  5. washThe combined organic layer was washed with water
  6. dry with materialdried over magnesium sulphate
  7. concentrationconcentrated to dryness under reduced pressure
  8. customto give a yellow gum
  9. custombp (60°-80°)

Sources & evidence

ORD record
ord-625359491db7411cbff7708b01489517
Source dataset
uspto-grants-1989_09
Patent number
US04866086

Reaction notes

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