1H-1,2,4-Triazole → HCID 14330161, compound

HRID 477401Notes

Reaction equation

HRID 477401 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([CH2:11][O:12][CH:13]3[CH2:18][CH2:17][CH2:16][CH2:15][O:14]3)[CH2:10][O:9]2)=[CH:4][CH:3]=1.[NH:19]1[CH:23]=[N:22][CH:21]=[N:20]1>CN(C)C=O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([OH:9])([CH2:10][N:19]2[CH:23]=[N:22][CH:21]=[N:20]2)[CH2:11][O:12][CH:13]2[CH2:18][CH2:17][CH2:16][CH2:15][O:14]2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 92571H-1,2,4-TriazoleHCID 14330160HCID 14330160, compound

Product 1

HCID 14330161HCID 14330161, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

37 g (0.138 mol) of 2-(4-chlorophenyl)-2-(tetrahydro-2H-pyran-2-yl-oxymethyl)-oxirane are added to a mixture of 22.4 g (0.32 mol) of 1,2,4-triazole, 5 g (0.04 mol) of potassium tert.-butylate and 300 ml of dimethylformamide at room temperature, while stirring. After the addition has ended, the reaction mixture is stirred at 80° C. for 12 hours and is then concentrated by stripping off the solvent under reduced pressure. Water is added to the residue which remains, the resulting mixture is extracted three times with methylene chloride and the combined organic phases are dried over magnesium sulphate and concentrated by stripping off the solvent under reduced pressure. The product thus obtained is purified chromatographically on silica gel with methylene chloride/ethyl acetate =4:1 as the mobile phase. 33.5 g (72% of theory) of 2-(4-chlorophenyl)-1-[(tetrahydro-2H-pyran-2-yl)-oxy]-3-(1,2,4-triazol-1-yl)-propan-2-ol are obtained in this manner in the form of pale yellow crystals of melting point 70° C.

Workup

  1. additionAfter the addition
  2. stirringthe reaction mixture is stirred at 80° C. for 12 hours
  3. concentrationis then concentrated
  4. additionWater is added to the residue which
  5. extractionthe resulting mixture is extracted three times with methylene chloride
  6. dry with materialthe combined organic phases are dried over magnesium sulphate
  7. concentrationconcentrated
  8. customThe product thus obtained
  9. customis purified chromatographically on silica gel with methylene chloride/ethyl acetate =4:1 as the mobile phase

Sources & evidence

ORD record
ord-d0938c004afb499db80e28149e1b4986
Source dataset
uspto-grants-1989_12
Patent number
US04888048

Reaction notes

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