1-Hexanethiol → HCID 68150146, compound

Participants

Reaction Steps

To hexanethiol (111 μL, 0.79 mmol) and sodium acetate trihydrate (108 mg, 0.79 mmol) in methanol (60 mL) was added in N-phenyl monobromomaleimide (200 mg, 0.79 mmol) in methanol (60 mL) dropwise over 1 hour with vigorous stirring. After 5 minutes solvent was removed in vacuo. Purification by column chromatography (gradient elution in 10% ethyl acetate in petroleum ether to 30% ethyl acetate in petroleum ether) afforded the desired compound as a pale yellow solid (109 mg, 0.38 mmol) in 48% yield. δH (600 MHz, CDCl3) 7.45 (dd, 2H, J=7.1 and 8.0, 2×H-12), 7.36 (d, 2H, J=6.0, H-11), 7.35 (d, 2H, J=8.1, 2×H-13), 6.19 (s, 1H, H-2), 2.96 (t, 2H, J=7.9, H2-10), 1.81-1.76 (m, 2H, H2-9), 1.50-1.45 (m, 2H, H2-8), 1.34-1.32 (m, 4H, H2-6 and H2-7), 0.91 (t, 3H, J=6.9, H3-5); δC (125 MHz, CDCl3) 168.59 (C═O), 166.96 (C═O), 152.20 (C3), 131.53 (C14), 129.21 (2×Ar—H), 127.93 (C11), 126.09 (2×Ar—H), 117.24 (C2), 32.03 (C10), 31.33 (CH2), 28.68 (CH2), 27.78 (CH2), 22.59 (CH2), 14.11 (C5); IR (oil, cm−1) 2931 (w), 1703 (s); MS (CI+) m/z (relative intensity): 290 ([M+H], 100); Exact Mass Calcd for [C16H20NO2S]+H requires m/z 290.1215 Found 290.1224 (CI+).

Provenance & Evidence