1H-1,2,4-Triazole → HCID 19811978, compound

HRID 373162Notes

Reaction equation

HRID 373162 reaction equation
[NH:1]1[CH:5]=[N:4][CH:3]=[N:2]1.C(=O)([O-])[O-].[K+].[K+].Cl[CH2:13][C:14]([C:24]1([CH3:29])[CH2:28][CH2:27][CH2:26][CH2:25]1)([OH:23])[CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[Cl:22]>CN(C)C=O>[Cl:22][C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=1[CH2:15][C:14]([C:24]1([CH3:29])[CH2:28][CH2:27][CH2:26][CH2:25]1)([OH:23])[CH2:13][N:1]1[CH:5]=[N:4][CH:3]=[N:2]1

Participants

5

Reactant 3

HCID 92571H-1,2,4-TriazoleHCID 11430Potassium CarbonateHCID 19811977HCID 19811977, compound

Product 1

HCID 19811978HCID 19811978, compoundYield 35.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
80 °C

Procedure

13 g (188 mmol) of 1,2,4-triazole and 18 g (130 mmol) of potassium carbonate are initially introduced into 30 ml of absolute dimethylformamide under a nitrogen atmosphere and the mixture is heated to 80° C. At this temperature, a solution of 17.1 g (59.6 mmol) of 1-chloro-3-(2-chlorophenyl)-2-(1-methyl-cyclopent-1-yl)-propan-2-ol in 20 ml of absolute dimethylformamide is added dropwise with stirring. The reaction mixture is then stirred at 80° C. for a further 8 hours. The precipitate is filtered off with suction, and the filtrate is concentrated by stripping off the diluent under reduced pressure. The residue is taken up in ethyl acetate, washed with water and, after drying over sodium sulphate, the solvent is stripped off under reduced pressure. The product which remains is chromatographed through a silica gel column using dichloromethane/ethanol=99:1 as the eluent. 6.8 g (35.7% of theory) of 1-(2-chlorophenyl)-2-(1-methyl-cyclopent- 1-yl)-3-(1,2,4-triazol-1-yl)-propan-2-ol are obtained in this way in the form of a solid substance of melting point 110° C.

Workup

  1. stirringThe reaction mixture is then stirred at 80° C. for a further 8 hours
  2. filtrationThe precipitate is filtered off with suction
  3. concentrationthe filtrate is concentrated
  4. washwashed with water
  5. dry with materialafter drying over sodium sulphate
  6. customThe product which remains is chromatographed through a silica gel column

Sources & evidence

ORD record
ord-687db918037647039b2ba18180043990
Source dataset
uspto-grants-1992_11
Patent number
US05162355

Reaction notes

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