S-ethyl chloromethanethioate

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

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

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

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

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

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

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

Procedure: In the same manner, S-ethyl chlorothioformate is reacted with each of 2-[4(1-methylpropylthio)phenylthio]ethanol, 2-[4(1-methylpropoxy)phenoxy]ethanol, 2-[4(3-methyl-2-butenylthio)phenylthio]ethanol and 2-[4(1-methylpropylthio)phenoxy]ethanol to give, respectively, compounds 64, 65, 66, 67 and 84 under Table A. to give

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

Procedure: In the same manner, S-ethyl chlorothioformate is reacted with each of 2-[4(1-methylpropylthio)phenylthio]ethanol, 2-[4(1-methylpropoxy)phenoxy]ethanol, 2-[4(3-methyl-2-butenylthio)phenylthio]ethanol and 2-[4(1-methylpropylthio)phenoxy]ethanol to give, respectively, compounds 64, 65, 66, 67 and 84 under Table A. to give

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

Procedure: 7 g of 2-[p-(phenylthio)phenoxy]ethylamine and 18.6 g of chlorothioformic acid S-ethyl ester are dissolved in 250 ml of acetone. 24 g of potassium carbonate are added to the solution and the mixture is heated under reflux for 6 hours. The mixture is then filtered, the residue is washed with acetone and the filtrate is evaporated in vacuo. The 13 g of residue are filtered through a 10-fold amount of silica gel with ether/cyclohexane (7:3). The first fractions yielded 10.2 g which, after recrystallization from ether/low boiling petroleum ether yields 6.3 g (76%) of 2-[p-(phenylthio)phenoxy]ethylthiocarbamic acid S-ethyl ester, m.p.--77°-79° C. the mixture is heated under reflux for 6 hours The mixture is then filtered the residue is washed with acetone the filtrate is evaporated in vacuo The 13 g of residue are filtered through a 10-fold amount of silica gel with ether/cyclohexane (7:3) The first fractions yielded 10.2 g which after recrystallization from ether/low

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

Procedure: 6.4 g of 2-(p-benzoylphenoxy)ethylamine and 17.2 g of chlorothioformic acid S-ethyl ester are dissolved in 230 ml of acetone, 22.2 g of potassium carbonate are added to the solution. The mixture is heated under reflux for 6 hours. After cooling to room temperature, the mixture is filtered, the residue is washed with acetone and the filtrate is evaporated in vacuo. The residue is suspended in hot ether and filtered. The residue is then washed with ether and the filtrate is evaporated in vacuo. Recrystallization of the residue from ether yields 2-(p-benzoylphenoxy)ethylthiocarbamic acid S-ethyl ester, m.p.--90°-92° C. Recrystallization of the mother liquor yields a further 1 g of product. The mixture is heated under reflux for 6 hours the mixture is filtered the residue is washed with acetone the filtrate is evaporated in vacuo filtered The residue is then washed with ether the filtrate is evaporated in vacuo Recrystallization of the residue from ether

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

Procedure: 4 g of 2-[(p-phenoxy)phenoxy]ethylamine and 11.2 g of chlorothioformic acid S-ethyl ester are dissolved in 150 ml of acetone. 14.5 g of potassium carbonate are added to the solution. This mixture is heated under reflux for 6 hours and then filtered. The residue is washed with acetone and the filtrate is evaporated in vacuo. The crystalline residue is suspended in cyclohexane and filtered to yield 2.5 g (53%) of 2-[(p-phenoxy)phenoxy]ethylthiocarbamic acid S-ethyl ester, m.p.--56°-58° C. This mixture is heated under reflux for 6 hours filtered The residue is washed with acetone the filtrate is evaporated in vacuo filtered

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

Procedure: The crude 5-hydroxy-1-methylpyrazol-4-yl 3-(2,2-dimethoxyethoxy)-2-methyl-4-(methylsulfonyl)phenyl ketone obtained in the above step (3) was dissolved in anhydrous THF (10 mL), and triethylamine (250 mg) and, 96% S-ethyl chlorothiolformate (200 mg) were added, followed by stirring for 1 hour at room temperature. Ethyl acetate (200 mL) was added to the obtained reaction mixture, and the mixture was washed twice with a saturated brine. The organic layer was dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=1:1) to obtain the desired product (150 mg). the mixture was washed twice with a saturated brine The organic layer was dried over anhydrous sodium sulfate the solvent was distilled off under reduced pressure The residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=1:1)