S-amino benzenecarbothioate

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

実験手順: To a stirred solution of KOH (560 mg, 10 mmol) in water (15 mL) was added thiobenzoic acid (690 mg, 5 mmol) and hydroxylamine-O-sulfonic acid (565 mg, 5 mmol). The solution was stirred for 20 min at room temperature. The white solid (S-benzoylthiohydroxylamine) was collected by filtration and then dissolved in CH2Cl2 (10 mL). To this mixture was added phenyl isocyanate (1.19 g, 10 mmol). The resulting solution was allowed to stir overnight at room temperature. The crude product was collected by the filtration and recrystallized in CH2Cl2/hexane. Pure compound 14 was obtained as a white solid (overall yield 60%). m.p. 184-186° C.; 1H NMR (300 MHz, DMSO-d6) δ 9.11 (s, 1H), 7.99 (s, 1H), 7.88 (d, 7.5 Hz, 2H), 7.74 (t, J=8.1 Hz, 1H), 7.59 (t, J=7.5 Hz, 2H), 7.45 (d, J=7.5 Hz, 2H), 7.24 (t, J=7.8 Hz, 2H), 6.98 (t, J=7.2 Hz, 1H); 13C NMR (75 MHz, DMSO-d6) δ 193.4, 155.0, 140.1, 135.2, 134.6, 130.1, 129.4, 127.2, 123.1, 119.3; IR (thin film) cm−1 3286, 3240, 1697, 1638, 1541, 1474, 1459, 1207; MS m/z 273.1 [M+H]+; calcd for C14H13N2O2S 273.1. The white solid (S-benzoylthiohydroxylamine) was collected by filtration dissolved in CH2Cl2 (10 mL) to stir overnight at room temperature The crude product was collected by the filtration recrystallized in CH2Cl2/hexane

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

実験手順: To a stirred solution of KOH (560 mg, 10 mmol) in water (15 mL) was added thiobenzoic acid (690 mg, 5 mmol) and hydroxylamine-O-sulfonic acid (565 mg, 5 mmol). The solution was stirred for 20 min at room temperature. The white solid (S-benzoylthiohydroxylamine) was collected by filtration and then dissolved in CH2Cl2 (10 mL). To this mixture was added phenyl isocyanate (1.19 g, 10 mmol). The resulting solution was allowed to stir overnight at room temperature. The crude product was collected by the filtration and recrystallized in CH2Cl2/hexane. Pure compound 14 was obtained as a white solid (overall yield 60%). m.p. 184-186° C.; 1H NMR (300 MHz, DMSO-d6) δ 9.11 (s, 1H), 7.99 (s, 1H), 7.88 (d, 7.5 Hz, 2H), 7.74 (t, J=8.1 Hz, 1H), 7.59 (t, J=7.5 Hz, 2H), 7.45 (d, J=7.5 Hz, 2H), 7.24 (t, J=7.8 Hz, 2H), 6.98 (t, J=7.2 Hz, 1H); 13C NMR (75 MHz, DMSO-d6) δ 193.4, 155.0, 140.1, 135.2, 134.6, 130.1, 129.4, 127.2, 123.1, 119.3; IR (thin film) cm−1 3286, 3240, 1697, 1638, 1541, 1474, 1459, 1207; MS m/z 273.1 [M+H]+; calcd for C14H13N2O2S 273.1. The white solid (S-benzoylthiohydroxylamine) was collected by filtration dissolved in CH2Cl2 (10 mL) to stir overnight at room temperature The crude product was collected by the filtration recrystallized in CH2Cl2/hexane

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

実験手順: To a stirred solution of KOH (560 mg, 10 mmol) in water (15 mL) was added thiobenzoic acid (690 mg, 5 mmol) and hydroxylamine-O-sulfonic acid (565 mg, 5 mmol). The solution was stirred for 20 min at rt. The white solid (S-benzoylthiohydroxylamine) was collected by filtration and then dissolved in CH2Cl2 (10 mL). To this mixture was added benzoic anhydride (2.26 g, 10 mmol). The resulting solution was allowed to stir overnight at rt. The crude product was purified by recrystallization (CH2Cl2/hexane) to give 2 as white solid. m.p. 138-140° C.; 1H NMR (300 MHz, CDCl3) δ 7.92 (m, 4H), 7.60 (m, 1H), 7.53 (m, 1H), 7.39 (m, 4H), 7.17 (s, 1H); 13C NMR (75 MHz, CDCl3) δ 190.0, 159.1, 134.6, 134.4, 133.3, 132.8, 129.3, 129.0, 128.0, 127.3; IR (thin film) cm−1 3265, 3062, 1696, 1659, 1451, 1419, 1257, 1207; HRMS m/z 258.0598 [M+H]+; calcd for C14H12NO2S 258.0589; overall yield: 64% (2 steps). The white solid (S-benzoylthiohydroxylamine) was collected by filtration dissolved in CH2Cl2 (10 mL) to stir overnight at rt The crude product was purified by recrystallization (CH2Cl2/hexane)

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

実験手順: To a stirred solution of KOH (560 mg, 10 mmol) in water (15 mL) was added thiobenzoic acid (690 mg, 5 mmol) and hydroxylamine-O-sulfonic acid (565 mg, 5 mmol). The solution was stirred for 20 min at room temperature. The white solid (S-benzoylthiohydroxylamine) was collected by filtration and then dissolved in CH2Cl2 (10 mL). To this mixture was added phenyl isocyanate (1.19 g, 10 mmol). The resulting solution was allowed to stir overnight at room temperature. The crude product was collected by the filtration and recrystallized in CH2Cl2/hexane. Pure compound 14 was obtained as a white solid (overall yield 60%). m.p. 184-186° C.; 1H NMR (300 MHz, DMSO-d6) δ 9.11 (s, 1H), 7.99 (s, 1H), 7.88 (d, 7.5 Hz, 2H), 7.74 (t, J=8.1 Hz, 1H), 7.59 (t, J=7.5 Hz, 2H), 7.45 (d, J=7.5 Hz, 2H), 7.24 (t, J=7.8 Hz, 2H), 6.98 (t, J=7.2 Hz, 1H); 13C NMR (75 MHz, DMSO-d6) δ 193.4, 155.0, 140.1, 135.2, 134.6, 130.1, 129.4, 127.2, 123.1, 119.3; IR (thin film) cm−1 3286, 3240, 1697, 1638, 1541, 1474, 1459, 1207; MS m/z 273.1 [M+H]+; calcd for C14H13N2O2S 273.1. The white solid (S-benzoylthiohydroxylamine) was collected by filtration dissolved in CH2Cl2 (10 mL) to stir overnight at room temperature The crude product was collected by the filtration recrystallized in CH2Cl2/hexane

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

実験手順: To a stirred solution of KOH (560 mg, 10 mmol) in water (15 mL) was added thiobenzoic acid (690 mg, 5 mmol) and hydroxylamine-O-sulfonic acid (565 mg, 5 mmol). The solution was stirred for 20 min at rt. The white solid (S-benzoylthiohydroxylamine) was collected by filtration and then dissolved in CH2Cl2 (10 mL). To this mixture was added benzoic anhydride (2.26 g, 10 mmol). The resulting solution was allowed to stir overnight at rt. The crude product was purified by recrystallization (CH2Cl2/hexane) to give 2 as white solid. m.p. 138-140° C.; 1H NMR (300 MHz, CDCl3) δ 7.92 (m, 4H), 7.60 (m, 1H), 7.53 (m, 1H), 7.39 (m, 4H), 7.17 (s, 1H); 13C NMR (75 MHz, CDCl3) δ 190.0, 159.1, 134.6, 134.4, 133.3, 132.8, 129.3, 129.0, 128.0, 127.3; IR (thin film) cm−1 3265, 3062, 1696, 1659, 1451, 1419, 1257, 1207; HRMS m/z 258.0598 [M+H]+; calcd for C14H12NO2S 258.0589; overall yield: 64% (2 steps). The white solid (S-benzoylthiohydroxylamine) was collected by filtration dissolved in CH2Cl2 (10 mL) to stir overnight at rt The crude product was purified by recrystallization (CH2Cl2/hexane)