2-isothiocyanatoethylbenzene

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:90.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 2-Phenylethyl isothiocyanate (0.36 g) was added to a stirred slurry of 2-amino-5-chlorobenzenesulfonamide sodium salt (0.50 g) in 5 ml of acetonitrile at 60° C. After 2½ h an additional amount of 2-phenylethyl isothiocyanate (0.18 g) was added, and the temperature was raised to 90° C. for 1½ h. The reaction mixture was treated with 1 ml of 4M acetic acid, 5 ml of ethanol and 0.1 g of charcoal and filtered through celite. The solvent was evaporated and the residue extracted with 10 ml of ethyl acetate. The solvent was evaporated and the oily residue was purified on a silica column eluted with ethyl acetate. The title compound was obtained as white crystals; m.p. 250-252° C. filtered through celite The solvent was evaporated the residue extracted with 10 ml of ethyl acetate The solvent was evaporated the oily residue was purified on a silica column eluted with ethyl acetate

Conditions: temp:90.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 2-Phenylethyl isothiocyanate (0.36 g) was added to a stirred slurry of 2-amino-5-chlorobenzenesulfonamide sodium salt (0.50 g) in 5 ml of acetonitrile at 60° C. After 2½ h an additional amount of 2-phenylethyl isothiocyanate (0.18 g) was added, and the temperature was raised to 90° C. for 1½ h. The reaction mixture was treated with 1 ml of 4M acetic acid, 5 ml of ethanol and 0.1 g of charcoal and filtered through celite. The solvent was evaporated and the residue extracted with 10 ml of ethyl acetate. The solvent was evaporated and the oily residue was purified on a silica column eluted with ethyl acetate. The title compound was obtained as white crystals; m.p. 250-252° C. filtered through celite The solvent was evaporated the residue extracted with 10 ml of ethyl acetate The solvent was evaporated the oily residue was purified on a silica column eluted with ethyl acetate

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

Procedure: The title compound was prepared by the procedure described in Example 16 using 16.3 g of phenethyl-isothiocyanate, 18.4 g of N-ethyl glycine, 20.2 g of triethyl amine, and 300 m/L of chloroform. Purification was achieved by flash chromatography on silica gel (20% ethyl acetate in hexane) The title compound (15.0 g) was obtained as an off-white solid, m.p. 66°-68° C. Anal. Calcd. for. C13H16N2O S: C, 62.87; H, 6.49; N, 11.28. Found: C, 63.03; H, 6.49; N, 11.32. Mass spectrum (EI, M.+) m/z 248. Purification was obtained as an off-white solid, m.p. 66°-68° C

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

Procedure: Vaniline (200 mg) and benzylamine (129 mg) were dissolved in methanol (3 ml) and the solution was stirred for 30 minutes. To the solution was added a catalytic amount of 10% platinum/carbon to be subjected to the hydrogenation reaction (1 atm). After the completion of the reaction, the resulting mixture was filtered and evaporated under reduced pressure to remove methanol. The obtained residue was dissolved in dichloromethane (3 ml) and to the solution was added phenethylisothiocyanate (196 mg, 1.2 mmol), followed by stirring at room temperature for 5 hours. Then, dichloromethane was evaporated under reduced pressure and the obtained residue was column-chromatographed (hexane/ethyl acetate=1/1) to yield the compound 25-1 (400 mg, 82%) as a white solid. to be subjected to the hydrogenation reaction (1 atm) After the completion of the reaction the resulting mixture was filtered evaporated under reduced pressure to remove methanol The obtained residue was dissolved in dichloromethane (3 ml) and to the solution by stirring at room temperature for 5 hours Then, dichloromethane was evaporated under reduced pressure the obtained residue was column-chromatographed (hexane/ethyl acetate=1/1)

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

Procedure: (1-methyl-1H-pyrrol-2-yl)methylamine (65 mg) and (2-isothiocyanatoethyl)benzene (100 mg) were dissolved in ethyl acetate (20 ml) and the solution was stirred for 12 hours. After the completion of the reaction, the resulting mixture was purified by column-chromatography (ethyl acetate/hexane=1/3) to yield the compound 17-3 (97 mg, 60%) as a brown liquid. After the completion of the reaction the resulting mixture was purified by column-chromatography (ethyl acetate/hexane=1/3)

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

Procedure: (1-methyl-1H-pyrrol-2-yl)methylamine (65 mg) and (2-isothiocyanatoethyl)benzene (100 mg) were dissolved in ethyl acetate (20 ml) and the solution was stirred for 12 hours. After the completion of the reaction, the resulting mixture was purified by column-chromatography (ethyl acetate/hexane=1/3) to yield the compound 17-3 (97 mg, 60%) as a brown liquid. After the completion of the reaction the resulting mixture was purified by column-chromatography (ethyl acetate/hexane=1/3)

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

Procedure: (1H-indol-5-yl)methylamine (8.5 mg) prepared in Step 1 was dissolved in dimethylformamide (100 μl) and the solution was diluted with dichloromethane (1 ml). To the diluted solution was added phenethylisothiocyanate (40 μl) and the mixture was stirred at room temperature for 2 hours. The resulting mixture was concentrated under reduced pressure and the obtained residue was chromatographed on a silica gel column eluting with ethyl acetate/hexane (2/3) to yield 1-(1H-indol-5-ylmethyl)-3-phenethylthiourea (15 mg, 83%). The resulting mixture was concentrated under reduced pressure the obtained residue was chromatographed on a silica gel column eluting with ethyl acetate/hexane (2/3)