* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Reference：
[1] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 9, p. 3044 - 3049
2
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Yield
Reaction Conditions
Operation in experiment
59%
With benzyltrimethylazanium tribroman-2-uide In acetic acid at 20℃; for 14 h;
Thiourea 14 (105 mg, 0.56 mmol) was dissolved in 10 ml acetic acid. Benzyltrimethylammonium tribromide (329 mg, 0.84 mmol) was added and the reaction was stirred at rt for 14h. Acetic acid was removed in vacuo and the residue redissolved in 15 ml DCM. 10 ml 0.5 n aqueous NaOH was added and the aqueous phase was extracted with DCM (2 x 15 ml). The combined organic layers were filtered through a phase separator and the solvent was removed in vacuo. The crude product was purified by flash column chromatography with pentane-ethyl acetate (12:5) as eluent to yield 15 (61 mg, 59percent) as a white solid: 1H NMR (500 MHz, CD3OD) 7.05 (dd, J=8.4, 2.0 Hz, 1H), 7.35 (d, 2.0 Hz, 1H), 7.53 (d, J=8.4 Hz, 1H); 13C NMR (125 MHz, CD3OD) 117.41, 121.45, 121.60, 129.37, 131.55, 153.24, 170.04MS (ESI): m/z 185 [M+H]+.
Reference：
[1] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 14, p. 4839 - 4843
[2] Yakugaku Zasshi, 1957, vol. 77, p. 649,651[3] Chem.Abstr., 1957, p. 16435
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