2-amino-3-chlorobenzenethiol

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: The 2-amino-3-chlorobenzenthiol (550 mg, 3.95 mmol) was dissolved in EtOH (10 mL) followed by KOH (220 mg, 3.95 mmol). To this mixture was added a solution of 1,2-dichloro-3-nitrobenzene (760 mg, 3.95 mmol) in EtOH (10 mL). The resulting reaction mixture was refluxed for 8 h to 12 h. The reaction was allowed to cool to room temperature and the residue was extracted with EtOAc and 1 mol dm−3 H3PO4. The organic layer was dried over MgSO4, filtered and evaporated to give a crude material. This crude material was purified by flash silica gel chromatography. The resulting reaction mixture was refluxed for 8 h to 12 h the residue was extracted with EtOAc and 1 mol dm−3 H3PO4 The organic layer was dried over MgSO4 filtered evaporated

反応条件: temp:150.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: The 4-chlorobenzo[d]thiazol-2-amine (2.00 g, 10.83 mmol) was combined with KOH (10.0 g, 178.2 mmol) and H2O (20 mL). The rsulting mixture was heated at 150° C. overnight. The solid became a thick paste overnight. After 24 h, the mixture was allowed to cool to room temperatureand diluted with H2O. A solution of AcOH was added to bring the pH down to 4 to 5. After 24 h to cool to room temperatureand

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

実験手順: 18.4 g of N,N'-carbonyldiimidazole was gradually added to a solution containing 20.5 g of N-tert-butoxycarbonyl-D-alanine dissolved in 200 mL of tetrahydrofuran, and the reaction mixture was stirred for 30 minutes at room temperature. 16.5 g of 2-amino-3-chlorothiophenol was added to the reaction mixture, and the whole mixture was refluxed for 3 hours. After completion of the reaction, the resulting mixture was poured into ice-cold water. The organic layer was extracted with ethyl acetate, washed using water, and then dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure. The residue was purified by column chromatography on silica gel, thus yielding 16.8 g of (R)-N-tert-butoxycarbonyl-1-(4-chloro-2-benzothiazolyl)ethylamine (melting point: 95°~96° C.). Furthermore, a hydrogen chloride gas was bubbled into a solution containing 10 g of the crystals obtained above dissolved in 50 mL of methylene chloride, for 3 hours at room temperature. After completion of the reaction, the reaction mixture was extracted with water, and was made basic using a saturated aqueous solution of sodium bicarbonate. The solution was extracted with ethyl acetate, washed with water, and then dried over anhydrous magnesium sulfate, followed by concentration under reduced pressure. The residue was purified by column chromatography on silica gel to afford 5.7 g (yield 84%) of the desired product. the whole mixture was refluxed for 3 hours After completion of the reaction the resulting mixture was poured into ice-cold water The organic layer was extracted with ethyl acetate washed dried over anhydrous sodium sulfate The solvent was removed under reduced pressure The residue was purified by column chromatography on silica gel

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

実験手順: 18.4 g of N,N'-carbonyldiimidazole was gradually added to a solution containing 20.5 g of N-tert-butoxycarbonyl-D-alanine dissolved in 200 mL of tetrahydrofuran, and the reaction mixture was stirred for 30 minutes at room temperature. 16.5 g of 2-amino-3-chlorothiophenol was added to the reaction mixture, and the whole mixture was refluxed for 3 hours. After completion of the reaction, the resulting mixture was poured into ice-cold water. The organic layer was extracted with ethyl acetate, washed using water, and then dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure. The residue was purified by column chromatography on silica gel, thus yielding 16.8 g of (R)-N-tert-butoxycarbonyl-1-(4-chloro-2-benzothiazolyl)ethylamine (melting point: 95°~96° C.). Furthermore, a hydrogen chloride gas was bubbled into a solution containing 10 g of the crystals obtained above dissolved in 50 mL of methylene chloride, for 3 hours at room temperature. After completion of the reaction, the reaction mixture was extracted with water, and was made basic using a saturated aqueous solution of sodium bicarbonate. The solution was extracted with ethyl acetate, washed with water, and then dried over anhydrous magnesium sulfate, followed by concentration under reduced pressure. The residue was purified by column chromatography on silica gel to afford 5.7 g (yield 84%) of the desired product. the whole mixture was refluxed for 3 hours After completion of the reaction the resulting mixture was poured into ice-cold water The organic layer was extracted with ethyl acetate washed dried over anhydrous sodium sulfate The solvent was removed under reduced pressure The residue was purified by column chromatography on silica gel

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

実験手順: The 2-amino-3-chlorobenzenthiol (550 mg, 3.95 mmol) was dissolved in EtOH (10 mL) followed by KOH (220 mg, 3.95 mmol). To this mixture was added a solution of 1,2-dichloro-3-nitrobenzene (760 mg, 3.95 mmol) in EtOH (10 mL). The resulting reaction mixture was refluxed for 8 h to 12 h. The reaction was allowed to cool to room temperature and the residue was extracted with EtOAc and 1 mol dm−3 H3PO4. The organic layer was dried over MgSO4, filtered and evaporated to give a crude material. This crude material was purified by flash silica gel chromatography. The resulting reaction mixture was refluxed for 8 h to 12 h the residue was extracted with EtOAc and 1 mol dm−3 H3PO4 The organic layer was dried over MgSO4 filtered evaporated

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

実験手順: The 2-amino-3-chlorobenzenthiol (550 mg, 3.95 mmol) was dissolved in EtOH (10 mL) followed by KOH (220 mg, 3.95 mmol). To this mixture was added a solution of 1,2-dichloro-3-nitrobenzene (760 mg, 3.95 mmol) in EtOH (10 mL). The resulting reaction mixture was refluxed for 8 h to 12 h. The reaction was allowed to cool to room temperature and the residue was extracted with EtOAc and 1 mol dm−3 H3PO4. The organic layer was dried over MgSO4, filtered and evaporated to give a crude material. This crude material was purified by flash silica gel chromatography. The resulting reaction mixture was refluxed for 8 h to 12 h the residue was extracted with EtOAc and 1 mol dm−3 H3PO4 The organic layer was dried over MgSO4 filtered evaporated

反応条件: temp:150.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: The 4-chlorobenzo[d]thiazol-2-amine (2.00 g, 10.83 mmol) was combined with KOH (10.0 g, 178.2 mmol) and H2O (20 mL). The rsulting mixture was heated at 150° C. overnight. The solid became a thick paste overnight. After 24 h, the mixture was allowed to cool to room temperatureand diluted with H2O. A solution of AcOH was added to bring the pH down to 4 to 5. After 24 h to cool to room temperatureand

反応条件: temp:150.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: The 4-chlorobenzo[d]thiazol-2-amine (2.00 g, 10.83 mmol) was combined with KOH (10.0 g, 178.2 mmol) and H2O (20 mL). The rsulting mixture was heated at 150° C. overnight. The solid became a thick paste overnight. After 24 h, the mixture was allowed to cool to room temperatureand diluted with H2O. A solution of AcOH was added to bring the pH down to 4 to 5. After 24 h to cool to room temperatureand

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

実験手順: Employing the procedure of Example 1, parts A and B with 3-methylpyrimidine-2,4(1H,3H)-dione and 2-amino-3-chlorobenzenethiol yielded the title compound.

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: Employing the procedure of Example 1, parts A and B with 3-methylpyrimidine-2,4(1H,3H)-dione and 2-amino-3-chlorobenzenethiol yielded the title compound.