3,4-Dichloro-1,2-benzenediamine

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: 5,6-Dichloro-1,2-phenylenediamine (200.0 g, 1.13 mol), isopropyl isothiocyanate (122.0 g, 1.21 mol), 1-cyclohexyl-3-(2-morpholinoethyl)carbodiimide metho-p-toluenesulfonate (622.0 g, 1.47 mol) and pyridine (4 L) were used according to general procedure I. The product was recrystallized from acetonitrile to give 184 g (67%) of a brown solid. Analytical data were consistent with those reported above. The product was recrystallized from acetonitrile

反应条件: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: 5,6-Dichloro-1,2-phenylenediamine (0.61 g, 3.4 mmol), and isopropyl isothiocyanate (0.39 g, 3.8 mmol) were combined in anhydrous pyridine (10 mL) and were heated to 80° C. for 15 min. Dicyclohexylcarbodiimide (1.06 g, 5.14 mmol) was then added and the resulting mixture was allowed to stir at 100° C. for 5 h. Toluene (30 mL) was added and the mixture was concentrated by rotary evaporation leaving a brown residue. The product was further purified by silica gel chromatography using 6.5:3:0.5 ethyl acetate/hexane/triethylamine to afford a gummy solid which was recrystallised from acetonitrile to give 0.46 g (60%) of a tan solid; m.p. 218-220° C. the mixture was concentrated by rotary evaporation leaving a brown residue The product was further purified by silica gel chromatography to afford a gummy solid which was recrystallised from acetonitrile

反应条件: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: 5,6-Dichloro-1,2-phenylenediamine (0.61 g, 3.4 mmol), and isopropyl isothiocyanate (0.39 g, 3.8 mmo) were combined in anhydrous pyridine (10 mL) and were heated to 80° C. for 15 min. Dicyclohexylcarbodiimide (1.06 g, 5.14 mmol) was then added and the resulting mixture was allowed to stir at 100° C. for 5 h. Toluene (30 mL) was added and the mixture was concentrated by rotary evaporation leaving a brown residue. The product was flilrer purified by silica gel chromatography using 6.5:3:0.5 ethyl acetatelhexane/triethylamine to afford a gummy solid which was recrystallised from acetonitrile to give 0.46 g (60%) of a tan solid; m.p. 218-220° C. Anal. Calcd for C10H11Cl2N3 : C, 49.20; H, 4.54; N, 17.21. Found: C. 49.31; H, 4.59; N, 17.33. the mixture was concentrated by rotary evaporation leaving a brown residue The product was flilrer purified by silica gel chromatography to afford a gummy solid which was recrystallised from acetonitrile

反应条件: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: 5,6-Dichloro-1,2-phenylenediamine (0.61 g, 3.4 mmol), and isopropyl isothiocyanate (0.39 g, 3.8 mmo) were combined in anhydrous pyridine (10 mL) and were heated to 80° C. for 15 min. Dicyclohexylcarbodiimide (1.06 g, 5.14 mmol) was then added and the resulting mixture was allowed to stir at 100° C. for 5 h. Toluene (30 mL) was added and the mixture was concentrated by rotary evaporation leaving a brown residue. The product was flilrer purified by silica gel chromatography using 6.5:3:0.5 ethyl acetatelhexane/triethylamine to afford a gummy solid which was recrystallised from acetonitrile to give 0.46 g (60%) of a tan solid; m.p. 218-220° C. Anal. Calcd for C10H11Cl2N3 : C, 49.20; H, 4.54; N, 17.21. Found: C. 49.31; H, 4.59; N, 17.33. the mixture was concentrated by rotary evaporation leaving a brown residue The product was flilrer purified by silica gel chromatography to afford a gummy solid which was recrystallised from acetonitrile

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: 5,6-Dichloro-1,2-phenylenediamine (200.0 g, 1.13 mol), isopropyl isothiocyanate (122.0 g, 1.21 mol), 1-cyclohexyl-3-(2-morpholinoethyl)carbodiimide metho-p-toluenesulfonate (622.0 g, 1.47 mol) and pyridine (4 L) were used according to general procedure I. The product was recrystallized from acetonitrile to give 184 g (67%) of a brown solid. Analytical data were consistent with those reported above. The product was recrystallized from acetonitrile

反应条件: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: 5,6-Dichloro-1,2-phenylenediamine (0.61 g, 3.4 mmol), and isopropyl isothiocyanate (0.39 g, 3.8 mmol) were combined in anhydrous pyridine (10 mL) and were heated to 80° C. for 15 min. Dicyclohexylcarbodiimide (1.06 g, 5.14 mmol) was then added and the resulting mixture was allowed to stir at 100° C. for 5 h. Toluene (30 mL) was added and the mixture was concentrated by rotary evaporation leaving a brown residue. The product was further purified by silica gel chromatography using 6.5:3:0.5 ethyl acetate/hexane/triethylamine to afford a gummy solid which was recrystallised from acetonitrile to give 0.46 g (60%) of a tan solid; m.p. 218-220° C. the mixture was concentrated by rotary evaporation leaving a brown residue The product was further purified by silica gel chromatography to afford a gummy solid which was recrystallised from acetonitrile

反应条件: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: 5,6-Dichloro-1,2-phenylenediamine (0.61 g, 3.4 mmol), and isopropyl isothiocyanate (0.39 g, 3.8 mmo) were combined in anhydrous pyridine (10 mL) and were heated to 80° C. for 15 min. Dicyclohexylcarbodiimide (1.06 g, 5.14 mmol) was then added and the resulting mixture was allowed to stir at 100° C. for 5 h. Toluene (30 mL) was added and the mixture was concentrated by rotary evaporation leaving a brown residue. The product was flilrer purified by silica gel chromatography using 6.5:3:0.5 ethyl acetatelhexane/triethylamine to afford a gummy solid which was recrystallised from acetonitrile to give 0.46 g (60%) of a tan solid; m.p. 218-220° C. Anal. Calcd for C10H11Cl2N3 : C, 49.20; H, 4.54; N, 17.21. Found: C. 49.31; H, 4.59; N, 17.33. the mixture was concentrated by rotary evaporation leaving a brown residue The product was flilrer purified by silica gel chromatography to afford a gummy solid which was recrystallised from acetonitrile

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: 3,4-Dichloro-1,2-phenylenediamine (8.00 g, 45.19 mmol), isopropyl isothiocyanate (5.26 g, 51.99 mmol), 1-cyclohexyl-3-(2-morpholinoethyl)carbodiimide metho-p-toluenesulfonate (25.0, 59.02 mmol), and pyridine (250 mL) were used according to general procedure I. The product was recrystallized from 1,4-dioxane to afford 6.12 g (55%) of a white solid. MS (EI): m/z 244 (M+H); 1H NMR (DMSO-d6) δ: 11.08 (s, 1H, NH), 7.07 (d, J=8.3Hz, 1H, ArH), 7.00 (brs, 1H, NH), 6.99 (d, J=8.3Hz, 1H, ArH), 3.91 (m, 1H, CH), 1.21 (d, J=6.5 Hz, 6H, overlapping CH3). The product was recrystallized from 1,4-dioxane

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: 2,3-Dichloro-6-nitroaniline (20.11 g, 97.14 mmol), Raney nickel (Aldrich, Milwaukee, slurry in water, 4.78 g wet), and ethanol (250 mL) were combined in an autoclave which was presssurized to 150 psig with hydrogen. The resulting reaction mixture was allowed to stir at rt overnight. The mixture was then filtered through a pad of Celite, which was subsequently washed with several portions of methanol, and the solvents were removed by rotary evaporation to leave a dark brown solid. The solid was slurried in hexanes and was collected on a Büchner funnel to afford 16.31 g (95%) of a brown solid. MS (EI): m/z 177.0 (M+H); 1H NMR (DMSO-d6) δ: 6.60 (d, J=8.3 Hz, 1H, ArH), 6.49 (d, J=8.4 Hz, 1H, ArH), 4.98 (br s, 4H, overlapping NH2). The resulting reaction mixture The mixture was then filtered through a pad of Celite, which was subsequently washed with several portions of methanol the solvents were removed by rotary evaporation to leave a dark brown solid was collected on a Büchner funnel

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: 2,3-Dichloro-6-nitroaniline (20.11 g, 97.14 mmol), Raney nickel (Aldrich, Milwaukee, slurry in water, 4.78 g wet), and ethanol (250 mL) were combined in an autoclave which was presssurized to 150 psig with hydrogen. The resulting reaction mixture was allowed to stir at rt overnight. The mixture was then filtered through a pad of Celite, which was subsequently washed with several portions of methanol, and the solvents were removed by rotary evaporation to leave a dark brown solid. The solid was slurried in hexanes and was collected on a Büchner funnel to afford 16.31 g (95%) of a brown solid. MS (EI): m/z 177.0 (M+H); 1H NMR (DMSO-d6) δ: 6.60 (d, J=8.3 Hz, 1H, ArH), 6.49 (d, J=8.4 Hz, 1H, ArH), 4.98 (br s, 4H, overlapping NH2). The resulting reaction mixture The mixture was then filtered through a pad of Celite, which was subsequently washed with several portions of methanol the solvents were removed by rotary evaporation to leave a dark brown solid was collected on a Büchner funnel

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: 5,6-Dichloro-1,2-phenylenediamine (0.61 g, 3.4 mmol), isopropyl isothiocyanate (0.39 g, 3.8 mmol), dicyclohexyl carbodiimide (1.06 g, 5.14 mmol) and pyridine (10 L) were used according to general procedure I. The product was recrystallized from acetonitrile to afford a tan solid (0.46 g, 60%); m.p. 218-220° C. The product was recrystallized from acetonitrile

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: 2,3-Dichloro-6-nitroaniline (20.11 g, 97.14 mmol), Raney-nickel (4.78 g of a 50% slurry in water), and ethanol (250 mL) were combined in an autoclave which was pressurized to 150 psig with hydrogen. The resulting reaction mixture was allowed to stir at RT overnight. The mixture was then filtered through a pad of celite, which was subsequently washed with several portions of methanol, and the solvents were removed by rotary evaporation to leave a dark brown solid. The solid was slurried and in hexanes and was collected on a Büchner funnel to afford 16.31 g (95%) of a brown solid. MS (EI): m/z 177.0 (M+H). The resulting reaction mixture The mixture was then filtered through a pad of celite, which was subsequently washed with several portions of methanol the solvents were removed by rotary evaporation to leave a dark brown solid was collected on a Büchner funnel