| 98% |
In ethanol; at 80.0℃; under 1500.15 Torr; |
2-bromo-l-phenylethan-l-one (1.0 equivalent, 0.5 mmol) and l-(4-bromophenyl)thiourea (1.0 equivalent, 0.5 mmol) were premixed in 2.5 mL of ethanol each in a separate vial. The solution was pumped through a preheated (80 C and 2 bar pressure) glass microfluidic reactor (Syrris Asia Flow Chemistry Module) at a 500 muIota7etaeta flow rate from two pumps to have the desired residence time of one minute in the glass microfluidic reactor. The output of the reactor was passed through a column packed with ion exchange resin (Amberlite IRA-900) to quench the hydrochloride produced as a side product and to prevent the clogging of back pressure regulator due to salt accumulation otherwise. The output was collected in a flask and concentrated under reduced pressure. The crude was suspended in 20 mL dichlorom ethane and washed with 2 x 10 mL satd. NaHCC . The organic phase was combined, dried MgS04 and concentrated under reduced pressure. The crude obtained was purified using prepacked silica cartridge on Teledyne CombiFlash R 200. Elution with 10:90 hexane-ethyl acetate afforded PA1 in 98% yield. The same methodology was used to synthesize other four compounds PA6, PA7, PA12, and PA14. For PA6, The product was obtained as a pale yellow powder, Yield 96% (138 mg). 1H MR (CDC13) delta 8.28 - 8.17 (m, 1H), 7.88 - 7.81 (m, 2H), 7.45 - 7.39 (m, 2H), 7.36 - 7.28 (m, 1H), 6.99 - 6.88 (m, 2H) and 6.86 (s, 1H); 13C NMR (101 MHz, CDC13) 5 163.59, 151.68, 134.47, 128.80, 128.18, 126.22, 120.24, 111.53, 111.32, 104.27, 104.04, 103.78 and 102.62. For PA7, The product was obtained as a pale yellow powder, Yield 92% (133 mg). 1H MR (C2D6SO) 5 10.11 (d, J= 1.6 Hz, 1H), 9.09 (dd, 7= 2.2, 0.9 Hz, 1H), 8.58 - 8.42 (m, 2H), 8.22 (ddd, 7= 7.9, 2.3, 1.6 Hz, 1H), 7.52 (s, 1H), 7.44 (ddd, 7= 8.0, 4.8, 0.9 Hz, 1H), 7.31 (ddd, 7= 11.7, 8.8, 2.9 Hz, 1H) and 7.17 - 7.07 (m, 1H); 13C NMR (C2D6SO) delta 164.18, 148.56, 147.01, 146.97, 133.02, 130.22, 123.96, 121.23, 111.48, 111.45, 111.23, 105.83, 104.35 and 104.12; mass spectrum (APCI), mlz calcd for Ci4Hi0F2N3S (M+H)+ 290.0558, found 290.0550. For PA12, The product was obtained as a colorless powder, Yield 94% (132 mg). 1H NMR (C2D6SO) delta 9.03 (dd, 7= 2.3, 0.9 Hz, 1H), 8.45 (dd, 7= 4.8, 1.6 Hz, 1H), 8.19 - 8.12 (m, 1H), 7.82 (t, 7= 5.4 Hz, 1H), 7.40 (ddd, 7= 8.0, 4.8, 0.9 Hz, 1H), 7.33 - 7.25 (m, 4H), 7.21 (d, 7= 5.4 Hz, 2H) and 2.91 (t, 7 = 7.3 Hz, 2H); 13C NMR (C2D6SO) delta 168.82, 148.22, 147.22, 146.99, 139.55, 132.92, 130.65, 128.86, 128.52, 126.31, 123.84, 102.66, 46.25 and 34.84. For PA14, The product was obtained as a colorless powder, Yield 92% (133 mg). 1H NMR (CDC13) delta 7.83 - 7.72 (m, 2H), 7.39 - 7.32 (m, 2H), 7.12 - 7.01 (m, 4H) and 6.72 (s, 1H); 13C NMR (CDC13) delta 165.64, 163.96, 161.50, 160.37, 157.96, 150.43, 136.48, 130.81, 127.90, 120.97, 116.41, 116.19, 115.79, 115.57 and 101.35. |
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