1H-1,2,4-Triazole → HCID 23045838, compound

HRID 2107517Notes

Reaction equation

HRID 2107517 reaction equation
[NH:1]1[CH:5]=[N:4][CH:3]=[N:2]1.[H-].[Na+].Br[CH2:9][C:10]([C:18]1[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=1)([C:12]1[N:13]=[C:14]([CH3:17])[S:15][CH:16]=1)[OH:11]>CN(C)C=O>[F:24][C:21]1[CH:22]=[CH:23][C:18]([C:10]([C:12]2[N:13]=[C:14]([CH3:17])[S:15][CH:16]=2)([OH:11])[CH2:9][N:1]2[CH:5]=[N:4][CH:3]=[N:2]2)=[CH:19][CH:20]=1

Participants

5

Reactant 3

HCID 92571H-1,2,4-TriazoleHCID 24758Sodium hydrideHCID 23045840HCID 23045840, compound

Product 1

HCID 23045838HCID 23045838, compoundYield 29%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

At 10° C., a solution of 4.1 g (0.06 mol) of 1,2,4-triazole in 30 ml of dimethylformamide is added dropwise and with stirring to a suspension of 1.8 g (0.06 mol) of sodium hydride in 20 ml of dimethylformamide, and, after an hour, a solution of 12.6 g (0.04 mol) of 2-bromo-1-(4-fluorophenyl)-1-(2-methylthiazol-4-yl)-ethanol in 30 ml of dimethylformamide is likewise added dropwise at 0° C. and with stirring. When the addition is complete, the mixture is stirred for an hour at 20° C., for a further two hours at 70° C., for two hours at 90° C. and for a further hour at 110° C. For working up, the reaction mixture is cooled and evaporated in vacuo, the residue is taken up in 300 ml of dichloromethane, the solution is washed twice using 200 ml of water each time, dried over sodium sulphate and concentrated in vacuo the residue is chromatographed over silica gel (eluent: dichloromethane/methanol 10:1), and the product thus obtained is crystallized by stirring with 150 ml of diisopropyl ether. 3.5 g (29% of theory) of 1-(4-fluorophenyl)-1-(2-methylthiazol-4-yl)-2-(1,2,4-triazol-1-yl)-ethanol of melting point 120° C. are obtained.

Workup

  1. waitafter an hour
  2. additionWhen the addition
  3. stirringthe mixture is stirred for an hour at 20° C., for a further two hours at 70° C., for two hours at 90° C. and for a further hour at 110° C
  4. temperaturethe reaction mixture is cooled
  5. customevaporated in vacuo
  6. washthe solution is washed twice
  7. dry with materialdried over sodium sulphate
  8. concentrationconcentrated in vacuo the residue
  9. customis chromatographed over silica gel (eluent: dichloromethane/methanol 10:1)
  10. customthe product thus obtained
  11. customis crystallized
  12. stirringby stirring with 150 ml of diisopropyl ether

Sources & evidence

ORD record
ord-8be24e46f1f44cc1b3ec1672edb1a5a8
Source dataset
uspto-grants-1990_06
Patent number
US04935049

Reaction notes

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