Water → 3-Cyclohexyl-1-(5-methyl-1,3-dioxan-5-yl)-2-(1,2,4-triazol-1-yl)-propan-1-one

HRID 1731542Notes

Reaction equation

HRID 1731542 reaction equation
[OH-].[K+].O.[CH3:4][C:5]1([C:11](=[O:18])[CH2:12][N:13]2[CH:17]=[N:16][CH:15]=[N:14]2)[CH2:10][O:9][CH2:8][O:7][CH2:6]1.Br[CH2:20][CH:21]1[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1>CS(C)=O>[CH:21]1([CH2:20][CH:12]([N:13]2[CH:17]=[N:16][CH:15]=[N:14]2)[C:11]([C:5]2([CH3:4])[CH2:10][O:9][CH2:8][O:7][CH2:6]2)=[O:18])[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1

Participants

6

Reactant 4

HCID 962Water2×HCID 14797Potassium HydroxideHCID 137636Cyclohexane, (bromomethyl)-HCID 128556521-(5-Methyl-1,3-dioxan-5-yl)-2-(1,2,4-triazol-1-yl)-ethan-1-one

Product 1

HCID 134557193-Cyclohexyl-1-(5-methyl-1,3-dioxan-5-yl)-2-(1,2,4-triazol-1-yl)-propan-1-oneYield 52.1%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

2.96 g (0.05 mol) of powdered potassium hydroxide and 3 ml of water are added to a solution of 11.0 g (0.05 mol) of 1-(5-methyl-1,3-dioxan-5-yl)-2-(1,2,4-triazol-1-yl)-ethan-1-one in 40 ml of dimethylsulphoxide, with stirring. After 10 minutes, 9.6 g (0.05 mol) of bromomethylcyclohexane (90% pure) are added and the mixture is stirred at 50° C. for 6 hours. For working up, the cooled reaction mixture is poured onto 500 ml of water and extracted twice with 200 ml of diethyl ether each time, the combined ether extracts are washed twice with 100 ml of water each time and dried over sodium sulphate and the solvent is removed in vacuo. The oily residue crystallizes from methylene chloride/diethyl ether. 8.0 g (52.1 g of theory) of 3-cyclohexyl-1-(5-methyl-1,3-dioxan-5-yl)-2-(1,2,4-triazol-1-yl)-propan-1-one of melting point 68°-71 ° C. are obtained.

Workup

  1. stirringthe mixture is stirred at 50° C. for 6 hours
  2. customthe cooled reaction mixture
  3. extractionextracted twice with 200 ml of diethyl ether each time
  4. washthe combined ether extracts are washed twice with 100 ml of water each time
  5. dry with materialdried over sodium sulphate
  6. customthe solvent is removed in vacuo
  7. customThe oily residue crystallizes from methylene chloride/diethyl ether

Sources & evidence

ORD record
ord-d442e14ce9e04bb6a35536df45d93106
Source dataset
uspto-grants-1986_11
Patent number
US04622334

Reaction notes

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