Phenyl isocyanate → HCID 569822, compound

Participants

Reaction Steps

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.

Provenance & Evidence