Получение N-фенилцианотиоформамида 35

Общая методика.

К кипящему раствору 1 ммоля имина 7k в 15 мл абсолютного этанола при -10 ^oC прикапывали раствор этилата натрия, полученного при растворении 115 мг. (5 мг-атом) металлического натрия в 3-5 мл. абсолютного этанола. Реакционную смесь выдерживали при -10 ^oC 5 минут, затем выливали в 100 мл. 1%-ной соляной кислоты и экстрагировали 3х10 мл CH₂Cl_2. Объединенную органическую фазу сушили МgSO₄ и упаривали. Остаток хроматографировали на колонке с силикагелем (элюент – смесь петролейный эфир/CH₂Cl₂).

N-Фенилцианотиоформамид 35

 

 

Выход 35 (47%), оранжевые кристаллы, т.пл. 83-84 ^oС, лит. т. пл. 80 ^oС [145]. Найдено (%): С, 59.43; H, 3.73; N, 17.17. C₉H₉NOS. Вычислено (%): C, 59.23; H, 3.73; N, 17.27. Спектр ЯМР ¹H (CDCl₃, δ, м.д., J/Гц): 7.39 (м, 3Н, Ar), 7.80 (д, 2Н, J 8.1 Гц, Ar), 9.80 (с, 1Н, NH). ИК-спектр (KBr), ν/cm^-1: 3272 (N-Н), 3088 (С-Н), 2232 (CN), 1616, 1604, 1552, 1488, 1400, 1296, 1208, 1096, 904, 832, 760, 744, 684, 608, 508. Масс-спектр (ЭУ, 70 ЭВ), m/z (I_отн (%)): 162 [M]⁺ (13), 135 (100).

Литература

 

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