1-chloro-2-isothiocyanatoethane

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: A mixture of 4-amino-2-chlorobenzoic acid methyl ester (0.5 g) and 2-chloroethylisothiocyanate (0.26 mL) in THF (20 mL) was refluxed for 24 h. THF was distilled and the residue was purified by column chromatography (silica gel: eluent: hexane/EtOAc 3:1-1:1) to yield 2-chloro-4-(2-thiazolinylamino)benzoic acid methyl ester (74 mg). ESMS: m/z 271 (MH+). was refluxed for 24 h THF was distilled the residue was purified by column chromatography (silica gel: eluent: hexane/EtOAc 3:1-1:1)

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

Procedure: A mixture of 4-amino-2-chlorobenzoic acid methyl ester (0.5 g) and 2-chloroethylisothiocyanate (0.26 mL) in THF (20 mL) was refluxed for 24 h. THF was distilled and the residue was purified by column chromatography (silica gel: eluent: hexane/EtOAc 3:1-1:1) to yield 2-chloro-4-(2-thiazolinylamino)benzoic acid methyl ester (74 mg). ESMS: m/z 271 (MH+). was refluxed for 24 h THF was distilled the residue was purified by column chromatography (silica gel: eluent: hexane/EtOAc 3:1-1:1)

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

Procedure: 1-(2,3-dichlorophenyl)-2-(pyridin-4-yl)ethanamine (0.30 g, 1.13 mmol) in dichloromethane (6 mL) was added chloroethylisothiocyanate (0.097 mL, 0.988 mmol). The solution was stirred at room temperature for 1.5 hour, and quenched with water. The aqueous layer was extracted with dichloromethane (3×). The pooled organic layer was dried over magnesium sulfate. The mixture was filtered. The filtrate was added silica gel, and the solvents were removed under vacuum. Purification by chromatography on silica gel (2 to 10% methanol in dichloromethane) gave a crude material, which was recrystallized in methanol/water to give 1-(2,3-dichlorophenyl)-2-(pyridin-4-yl)-N-(thiazolidin-2-ylidene)ethanamine Compound 18 as a solid (15.9 mg, 0.045 mmol, 4% yield). quenched with water The aqueous layer was extracted with dichloromethane (3×) The pooled organic layer was dried over magnesium sulfate The mixture was filtered The filtrate was added silica gel the solvents were removed under vacuum Purification by chromatography on silica gel (2 to 10% methanol in dichloromethane) gave a crude material, which was recrystallized in methanol/water

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

Procedure: 1-(2,3-dichlorophenyl)-2-(pyridin-4-yl)ethanamine (0.30 g, 1.13 mmol) in dichloromethane (6 mL) was added chloroethylisothiocyanate (0.097 mL, 0.988 mmol). The solution was stirred at room temperature for 1.5 hour, and quenched with water. The aqueous layer was extracted with dichloromethane (3×). The pooled organic layer was dried over magnesium sulfate. The mixture was filtered. The filtrate was added silica gel, and the solvents were removed under vacuum. Purification by chromatography on silica gel (2 to 10% methanol in dichloromethane) gave a crude material, which was recrystallized in methanol/water to give 1-(2,3-dichlorophenyl)-2-(pyridin-4-yl)-N-(thiazolidin-2-ylidene)ethanamine Compound 18 as a solid (15.9 mg, 0.045 mmol, 4% yield). quenched with water The aqueous layer was extracted with dichloromethane (3×) The pooled organic layer was dried over magnesium sulfate The mixture was filtered The filtrate was added silica gel the solvents were removed under vacuum Purification by chromatography on silica gel (2 to 10% methanol in dichloromethane) gave a crude material, which was recrystallized in methanol/water

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

Procedure: To a solution of 4-chloro-indan-1-ylamine (390 mg) in diethyl ether (20 ml) was added 1-chloro-2-isothiocyanatoethane (283 mg) at 0° C. and the solution stirred for 2 h at the same temperature. The reaction mixture was quenched with diluted sodium hydroxide solution and extracted with diethyl ether. The residue was purified on silica gel to yield 240 mg of the product (41%). The reaction mixture was quenched with diluted sodium hydroxide solution extracted with diethyl ether The residue was purified on silica gel

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

Procedure: To a solution of 4-chloro-indan-1-ylamine (390 mg) in diethyl ether (20 ml) was added 1-chloro-2-isothiocyanatoethane (283 mg) at 0° C. and the solution stirred for 2 h at the same temperature. The reaction mixture was quenched with diluted sodium hydroxide solution and extracted with diethyl ether. The residue was purified on silica gel to yield 240 mg of the product (41%). The reaction mixture was quenched with diluted sodium hydroxide solution extracted with diethyl ether The residue was purified on silica gel

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

Procedure: To a solution of 4.0 g (0.03 mole) of oxindole in 125 ml dry glyme there is added 1.4 g (0.03 mole) of sodium hydride (50% oil dispersion) and the mixture is stirred at room temperature for 3 hours. 3.6 g (0.3 Mole) of 2-chloroethyl isothiocyanate in 5 ml of dry glyme is then added and the mixture is refluxed overnight. After evaporation of the solvent in vacuo, the residue is chromatographed on an Alumina Act. IV column. Elution with ethyl ether yields the product which is crystallized from ethyl ether to yield 0.6 g, m.p. 97°-99°. the mixture is refluxed overnight After evaporation of the solvent in vacuo the residue is chromatographed on an Alumina Act Elution with ethyl ether yields the product which is crystallized from ethyl ether to yield 0.6 g, m.p. 97°-99°

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

Procedure: To a solution of 4.0 g (0.03 mole) of oxindole in 125 ml dry glyme there is added 1.4 g (0.03 mole) of sodium hydride (50% oil dispersion) and the mixture is stirred at room temperature for 3 hours. 3.6 g (0.3 Mole) of 2-chloroethyl isothiocyanate in 5 ml of dry glyme is then added and the mixture is refluxed overnight. After evaporation of the solvent in vacuo, the residue is chromatographed on an Alumina Act. IV column. Elution with ethyl ether yields the product which is crystallized from ethyl ether to yield 0.6 g, m.p. 97°-99°. the mixture is refluxed overnight After evaporation of the solvent in vacuo the residue is chromatographed on an Alumina Act Elution with ethyl ether yields the product which is crystallized from ethyl ether to yield 0.6 g, m.p. 97°-99°

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

Procedure: 9.2 g of β-chloroethyl isothiocyanate dissolved in 20 ml tetrahydrofuran are added dropwise to a solution of 9 g of dicyclopropylmethylamine in 70 ml tetrahydrofuran. The reaction mixture is kept at a temperature of from 0° to +5° C. during the addition, then maintained at room temperature for 2 hours. The solvent is evaporated to dryness and the residue, consisting essentially of N-(1,1-dicyclopropylmethyl) N'-(β-chloroethyl) thiourea, is recovered and used without any further purification for the next step of the synthesis. The reaction mixture is kept at a temperature of from 0° to +5° C. during the addition The solvent is evaporated to dryness is recovered used without any further purification for the next step of the synthesis