trimethyl(tetradecyl)azanium

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of bis-(5-chloropyrid-2-yl)ketone (0.8 g), trimethylsulphoxonium iodide (0.84 g), cetrimide (0.08 g) and sodium hydroxide (3 g) in water (16 ml) and 1,1,1-trichloroethane (30 ml) was stirred vigorously and heated at 70° to 75° C. for 2.5 hours. Further trimethylsulphoxonium iodide (0.86 g) was added and the mixture heated at 75° to 80° C. for a further 2 hours. The mixture was cooled, diluted with water (10 ml) and extracted with dichloromethane (3×20 ml). The combined organic extracts were dried over magnesium sulfate and evaporated to yield the crude title compound as a brownish paste (0.8 g), which was used directly. heated at 70° to 75° C. for 2.5 hours the mixture heated at 75° to 80° C. for a further 2 hours The mixture was cooled extracted with dichloromethane (3×20 ml) The combined organic extracts were dried over magnesium sulfate evaporated

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 4'-chloro-2-methyl-2-(1H-1,2,4-triazol-1-yl)propiophenone (1.375 g), trimethyl sulphoxonium iodide (1.6 g), aqueous sodium hydroxide (5N; 13.5 ml.), cetrimide (80 mg.) and 1,1,1-trichloroethane (30 ml.) was heated at 80° for 24 hours. The solution was cooled and diluted with methylene chloride (30 ml.), and the organic layer was separated and dried (MgSO4). Removal of the solvent, followed by flash chromatography of the residue on silica (100 g.) using ethyl acetate/hexane/diethylamine (40:60:3 v/v/v) for elution, gave, after collection of appropriate fractions and evaporation, the title oxirane as an oil in 79% yield, 1.15 g. was heated at 80° for 24 hours The solution was cooled the organic layer was separated dried (MgSO4) Removal of the solvent for elution gave after collection of appropriate fractions and evaporation

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of bis-(5-chloropyrid-2-yl)ketone (0.8 g), trimethylsulphoxonium iodide (0.84 g), cetrimide (0.08 g) and sodium hydroxide (3 g) in water (16 ml) and 1,1,1-trichloroethane (30 ml) was stirred vigorously and heated at 70° to 75° C. for 2.5 hours. Further trimethylsulphoxonium iodide (0.86 g) was added and the mixture heated at 75° to 80° C. for a further 2 hours. The mixture was cooled, diluted with water (10 ml) and extracted with dichloromethane (3×20 ml). The combined organic extracts were dried over magnesium sulfate and evaporated to yield the crude title compound as a brownish paste (0.8 g), which was used directly. heated at 70° to 75° C. for 2.5 hours the mixture heated at 75° to 80° C. for a further 2 hours The mixture was cooled extracted with dichloromethane (3×20 ml) The combined organic extracts were dried over magnesium sulfate evaporated

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of bis-(5-chloropyrid-2-yl)ketone (0.8 g), trimethylsulphoxonium iodide (0.84 g), cetrimide (0.08 g) and sodium hydroxide (3 g) in water (16 ml) and 1,1,1-trichloroethane (30 ml) was stirred vigorously and heated at 70° to 75° C. for 2.5 hours. Further trimethylsulphoxonium iodide (0.86 g) was added and the mixture heated at 75° to 80° C. for a further 2 hours. The mixture was cooled, diluted with water (10 ml) and extracted with dichloromethane (3×20 ml). The combined organic extracts were dried over magnesium sulfate and evaporated to yield the crude title compound as a brownish paste (0.8 g), which was used directly. heated at 70° to 75° C. for 2.5 hours the mixture heated at 75° to 80° C. for a further 2 hours The mixture was cooled extracted with dichloromethane (3×20 ml) The combined organic extracts were dried over magnesium sulfate evaporated

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 2',4'-Dichloro-2-(1H-1,2,4-triazol-1-yl)prop-2-enophenone (0.27 g, 1.0 mMole) was added dropwise in 1,1,1-trichloroethane (2 ml) to a refluxing mixture of trimethylsulphoxonium iodide (0.33 g, 1.5 mMole), cetrimide (0.03 g), 1,1,1-trichloroethane (5 ml) and aqueous 2N sodium hydroxide (3 ml) with vigorous stirring over 2 minutes. After refluxing for a further 15 minutes the organic phase, after cooling was separated. Evaporation gave a gum, weight 0.11 g. After refluxing for a further 15 minutes the organic phase after cooling was separated Evaporation gave a gum

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 2',4'-Dichloro-2-(1H-1,2,4-triazol-1-yl)prop-2-enophenone (0.27 g, 1.0 mMole) was added dropwise in 1,1,1-trichloroethane (2 ml) to a refluxing mixture of trimethylsulphoxonium iodide (0.33 g, 1.5 mMole), cetrimide (0.03 g), 1,1,1-trichloroethane (5 ml) and aqueous 2N sodium hydroxide (3 ml) with vigorous stirring over 2 minutes. After refluxing for a further 15 minutes the organic phase, after cooling was separated. Evaporation gave a gum, weight 0.11 g. After refluxing for a further 15 minutes the organic phase after cooling was separated Evaporation gave a gum

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 1-(1-H-1,2,4-Triazol-1-yl)cyclopropyl 2,4-dichlorophenyl ketone (0.5 g, 1.8 mMole) was added to trimethylsulfphoxonium iodide (0.57 g, 2.6 mMole), cetrimide (0.02 g), 1,1,1-trichloroethane (10 ml) and aqueous sodium hydroxide solution (5 ml of 20%). The mixture was refluxed for twenty hours. The mixture was refluxed for twenty hours

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 1-(1-H-1,2,4-Triazol-1-yl)cyclopropyl 2,4-dichlorophenyl ketone (0.5 g, 1.8 mMole) was added to trimethylsulfphoxonium iodide (0.57 g, 2.6 mMole), cetrimide (0.02 g), 1,1,1-trichloroethane (10 ml) and aqueous sodium hydroxide solution (5 ml of 20%). The mixture was refluxed for twenty hours. The mixture was refluxed for twenty hours

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 1-(1-H-1,2,4-Triazol-1-yl)cyclopropyl 2,4-dichlorophenyl ketone (0.5 g, 1.8 mMole) was added to trimethylsulfphoxonium iodide (0.57 g, 2.6 mMole), cetrimide (0.02 g), 1,1,1-trichloroethane (10 ml) and aqueous sodium hydroxide solution (5 ml of 20%). The mixture was refluxed for twenty hours. The mixture was refluxed for twenty hours

Conditions: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a stirred solution of p-chlorophenacyl-1H-1,2,4-triazole (10.3 g, 40 mmol) in 65 mL of toluene and 65 mL of 20% w/w NaOH at 60° C., add trimethylsulfoxonium iodide (8.84 g, 40 mmol) and cetrimide (0.39 g). Continue to stir the so-formed mixture at 60° C. for 1.5 h. Separate the toluene layer, add 20 mL of H2O to the aqueous layer and extract with two 100 mL portions of ethyl acetate (EtOAc). Combine both the toluene and EtOAc layers, dry oyer MgSO4, filter, and evaporate off the solvents. Add 100 mL of acetone, 6 mL of concentrated H2SO4, 20 mL of H2O, and reflux for 3 hr. Eyaporate the acetone at 45° C. under reduced pressure. Add 20 mL of sat. sodium bicarbonate and extract with two 100 mL portions of EtOAc. Wash the combined EtOAc layers with sat. brine, dry oyer MgSO 4, and evaporate the EtOAc to obtain a syrup. Chromatograph the syrup on 300 g of silica gel using 5% MeOH/CH2Cl2 as the eluent under flash chromatography conditions to obtain 3.63 g of the title product. Separate the toluene layer add 20 mL of H2O to the aqueous layer extract with two 100 mL portions of ethyl acetate (EtOAc) Combine both the toluene and EtOAc layers, dry oyer MgSO4 filter evaporate off the solvents Add 100 mL of acetone, 6 mL of concentrated H2SO4, 20 mL of H2O reflux for 3 hr at 45° C. Add 20 mL of sat. sodium bicarbonate extract with two 100 mL portions of EtOAc Wash the combined EtOAc layers with sat. brine dry oyer MgSO 4 evaporate the EtOAc to obtain a syrup