1-chloro-4-(isothiocyanatomethyl)benzene

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Cyclohexylamine (10 mmol) was added dropwise to 4-chlorobenzylisothio-cyanate (10 mmol) dissolved in 20 ml of dry ether. The solution was stirred for 2 hours at room temperature. The precipitated product was filtered off and crystallized from ethyl acetate. 3-Piperidinopropyl chloride hydrochloride (3 mmol), the product (3 mmol), and ca-talytic amounts of potassium iodide were refluxed in ethanol for 6 days. Sub-sequently, ethanol was evaporated, and the residue was purified by column chromato-graphy (eluent: methylene chloride/methanol (95/5)). After evaporation of the solvent the product was crystallized with hydrochloric acid from diethyl ether/ethanol. The precipitated product was filtered off crystallized from ethyl acetate Sub-sequently, ethanol was evaporated the residue was purified by column chromato-graphy (eluent: methylene chloride/methanol (95/5)) After evaporation of the solvent the product was crystallized with hydrochloric acid from diethyl ether/ethanol

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Cyclohexylamine (10 mmol) was added dropwise to 4-chlorobenzylisothio-cyanate (10 mmol) dissolved in 20 ml of dry ether. The solution was stirred for 2 hours at room temperature. The precipitated product was filtered off and crystallized from ethyl acetate. 3-Piperidinopropyl chloride hydrochloride (3 mmol), the product (3 mmol), and ca-talytic amounts of potassium iodide were refluxed in ethanol for 6 days. Sub-sequently, ethanol was evaporated, and the residue was purified by column chromato-graphy (eluent: methylene chloride/methanol (95/5)). After evaporation of the solvent the product was crystallized with hydrochloric acid from diethyl ether/ethanol. The precipitated product was filtered off crystallized from ethyl acetate Sub-sequently, ethanol was evaporated the residue was purified by column chromato-graphy (eluent: methylene chloride/methanol (95/5)) After evaporation of the solvent the product was crystallized with hydrochloric acid from diethyl ether/ethanol

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: The compound 32-1 (100 mg) prepared according to the same procedure as described in Step 1 was dissolved in ethyl acetate (4 ml) and to the solution were added a solution of 4-chlorobenzylisothiocyanate (123 mg) in ethyl acetate (2 ml), followed by stirring at room temperarure for 18 hours. The obtained reaction mixture was concentrated under reduced pressure and purified by column-chromatography (hexane/ethyl acetate=2/1) to yield the compound 32-2 (201 mg, 99%). The obtained reaction mixture was concentrated under reduced pressure purified by column-chromatography (hexane/ethyl acetate=2/1)

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: The compound 32-1 (100 mg) prepared according to the same procedure as described in Step 1 was dissolved in ethyl acetate (4 ml) and to the solution were added a solution of 4-chlorobenzylisothiocyanate (123 mg) in ethyl acetate (2 ml), followed by stirring at room temperarure for 18 hours. The obtained reaction mixture was concentrated under reduced pressure and purified by column-chromatography (hexane/ethyl acetate=2/1) to yield the compound 32-2 (201 mg, 99%). The obtained reaction mixture was concentrated under reduced pressure purified by column-chromatography (hexane/ethyl acetate=2/1)

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Cyclohexylamine (10 mmol) was added dropwise to 4-chlorobenzylisothio-cyanate (10 mmol) dissolved in 20 ml of dry ether. The solution was stirred for 2 hours at room temperature. The precipitated product was filtered off and crystallized from ethyl acetate. 3-Piperidinopropyl chloride hydrochloride (3 mmol), the product (3 mmol), and ca-talytic amounts of potassium iodide were refluxed in ethanol for 6 days. Sub-sequently, ethanol was evaporated, and the residue was purified by column chromato-graphy (eluent: methylene chloride/methanol (95/5)). After evaporation of the solvent the product was crystallized with hydrochloric acid from diethyl ether/ethanol. The precipitated product was filtered off crystallized from ethyl acetate Sub-sequently, ethanol was evaporated the residue was purified by column chromato-graphy (eluent: methylene chloride/methanol (95/5)) After evaporation of the solvent the product was crystallized with hydrochloric acid from diethyl ether/ethanol

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Cyclohexylamine (10 mmol) was added dropwise to 4-chlorobenzylisothio-cyanate (10 mmol) dissolved in 20 ml of dry ether. The solution was stirred for 2 hours at room temperature. The precipitated product was filtered off and crystallized from ethyl acetate. 3-Piperidinopropyl chloride hydrochloride (3 mmol), the product (3 mmol), and ca-talytic amounts of potassium iodide were refluxed in ethanol for 6 days. Sub-sequently, ethanol was evaporated, and the residue was purified by column chromato-graphy (eluent: methylene chloride/methanol (95/5)). After evaporation of the solvent the product was crystallized with hydrochloric acid from diethyl ether/ethanol. The precipitated product was filtered off crystallized from ethyl acetate Sub-sequently, ethanol was evaporated the residue was purified by column chromato-graphy (eluent: methylene chloride/methanol (95/5)) After evaporation of the solvent the product was crystallized with hydrochloric acid from diethyl ether/ethanol

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a solution of 1.06 g. of 3-mercaptopropionic acid in 5 ml. of toluene and 2.0 g. of triethylamine, there was added with cooling 1.83 g. of p-chlorobenzylisothiocyanate. Two phases formed. The mixture was acidified with 1-N hydrochloric acid and extracted with chloroform. The chloroform phases were washed with water, dried over magnesium sulfate and concentrated. The residue was recrystallized from acetonitrile, and 2.1 g. of 3-{[(p-chlorobenzyl)thiocarbamoyl]thio}-propionic acid having a melting point of 126°-127° C. were obtained. with cooling 1.83 g Two phases formed extracted with chloroform The chloroform phases were washed with water dried over magnesium sulfate concentrated The residue was recrystallized from acetonitrile, and 2.1 g

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Cyclohexylamine (10 mmol) was added dropwise to 4-chlorobenzylisothio-cyanate (10 mmol) dissolved in 20 ml of dry ether. The solution was stirred for 2 hours at room temperature. The precipitated product was filtered off and crystallized from ethyl acetate. 3-Piperidinopropyl chloride hydrochloride (3 mmol), the product (3 mmol), and ca-talytic amounts of potassium iodide were refluxed in ethanol for 6 days. Sub-sequently, ethanol was evaporated, and the residue was purified by column chromato-graphy (eluent: methylene chloride/methanol (95/5)). After evaporation of the solvent the product was crystallized with hydrochloric acid from diethyl ether/ethanol. The precipitated product was filtered off crystallized from ethyl acetate Sub-sequently, ethanol was evaporated the residue was purified by column chromato-graphy (eluent: methylene chloride/methanol (95/5)) After evaporation of the solvent the product was crystallized with hydrochloric acid from diethyl ether/ethanol

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Cyclohexylamine (10 mmol) was added dropwise to 4-chlorobenzylisothio-cyanate (10 mmol) dissolved in 20 ml of dry ether. The solution was stirred for 2 hours at room temperature. The precipitated product was filtered off and crystallized from ethyl acetate. 3-Piperidinopropyl chloride hydrochloride (3 mmol), the product (3 mmol), and ca-talytic amounts of potassium iodide were refluxed in ethanol for 6 days. Sub-sequently, ethanol was evaporated, and the residue was purified by column chromato-graphy (eluent: methylene chloride/methanol (95/5)). After evaporation of the solvent the product was crystallized with hydrochloric acid from diethyl ether/ethanol. The precipitated product was filtered off crystallized from ethyl acetate Sub-sequently, ethanol was evaporated the residue was purified by column chromato-graphy (eluent: methylene chloride/methanol (95/5)) After evaporation of the solvent the product was crystallized with hydrochloric acid from diethyl ether/ethanol

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: The compound 32-1 (100 mg) prepared according to the same procedure as described in Step 1 was dissolved in ethyl acetate (4 ml) and to the solution were added a solution of 4-chlorobenzylisothiocyanate (123 mg) in ethyl acetate (2 ml), followed by stirring at room temperarure for 18 hours. The obtained reaction mixture was concentrated under reduced pressure and purified by column-chromatography (hexane/ethyl acetate=2/1) to yield the compound 32-2 (201 mg, 99%). The obtained reaction mixture was concentrated under reduced pressure purified by column-chromatography (hexane/ethyl acetate=2/1)