Potassium Hydroxide → HCID 13064955, compound

HRID 464920Notes

Reaction equation

HRID 464920 reaction equation
[OH-].[K+].[CH:3]1([CH2:9]Br)[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1.[Cl:11][C:12]1[CH:30]=[CH:29][C:15]([O:16][CH2:17][C:18]([CH3:28])([CH3:27])[C:19](=[O:26])[CH2:20][N:21]2[CH:25]=[N:24][CH:23]=[N:22]2)=[CH:14][CH:13]=1>O.CS(C)=O>[Cl:11][C:12]1[CH:13]=[CH:14][C:15]([O:16][CH2:17][C:18]([CH3:27])([CH3:28])[C:19](=[O:26])[CH:20]([N:21]2[CH:25]=[N:24][CH:23]=[N:22]2)[CH2:9][CH:3]2[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]2)=[CH:29][CH:30]=1

Participants

6

Reactant 3

HCID 14797Potassium HydroxideHCID 137636Cyclohexane, (bromomethyl)-HCID 13073537HCID 13073537, compound

Product 1

HCID 13064955HCID 13064955, compoundYield 47.7%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolvent2×HCID 962WaterSolvent2×

Procedure

First 5.6 g of potassium hydroxide in 12 ml of water and then 17.7 g (0.1 mol) of cyclohexylmethylbromide in 5 ml of dimethylsulphoxide were added dropwise to 29.3 g (0.1 mol) of 1-(4-chlorophenoxy)-2,2-dimethyl-4-(1,2,4-triazol-1-yl)-butan-3-one (prepared as described in Example 3) in 100 ml of dimethylsulphoxide at 20° C. The reaction mixture was subsequently stirred at room temperature for 15 hours, poured into 200 ml of water and extracted with 200 ml of methylene chloride. The organic phase was washed three times with 100 ml of water each time, dried over sodium sulphate and concentrated by distilling off the solvent. The residue was taken up in 100 ml of ether, whereupon the product crystallized out. 18.6 g (47% of theory) of 1-(4-chlorophenoxy)-5-cyclohexyl-2,2-dimethyl-4-(1,2,4-triazol-1-yl)-pentan-3-one of melting point 58°-60° C. were obtained.

Workup

  1. extractionextracted with 200 ml of methylene chloride
  2. washThe organic phase was washed three times with 100 ml of water each time
  3. dry with materialdried over sodium sulphate
  4. concentrationconcentrated
  5. distillationby distilling off the solvent
  6. customcrystallized out

Sources & evidence

ORD record
ord-91846cf92b6744fa83d826c5c723e3cb
Source dataset
uspto-grants-1985_10
Patent number
US04549900

Reaction notes

Loading…