Реакция #6005

Уравнение реакции

methyl isothiocyanate

(±)-2-(quinolin-3-yl)cyclohexanone

potassium t-butoxide

→

(±)-N-methyl-2-oxo-1-(quinolin-3-yl)cyclohexanecarbothioamide

Выход 9.4%

Растворители

tetrahydrofuran

tetrahydrofuran

Условия реакции

Обработка

1. 1
   ДругоеAfter 4 hours at 0° C. the reaction mixture was partitioned between saturated aqueous ammonium chloride solution (50 ml) and chloroform (50 ml)
2. 2
   ЭкстракцияThe aqueous layer was extracted again with chloroform (50 ml)
3. 3
   СушкаThe combined organic extracts were then dried over sodium sulphate
4. 4
   Концентрированиеconcentrated in vacuo (20° C.; 14 mmHg)
5. 5
   Другоеto give a crude oil which
6. 6
   Другоеwas purified by flash chromatography over silica gel eluting with ethyl acetate

Методика

A solution of (±)-2-(quinolin-3-yl)cyclohexanone (0.78 g, 3.5 mmol) in tetrahydrofuran (10 ml) at -5° C. was treated with potassium t-butoxide (0.43 g, 3.9 mmol) in one portion. After 25 minutes at -5° C. the deep red mixture was treated dropwise during 1 minute with a solution of methyl isothiocyanate (0.28 g, 3.9 mmol) in tetrahydrofuran (2 ml). After 4 hours at 0° C. the reaction mixture was partitioned between saturated aqueous ammonium chloride solution (50 ml) and chloroform (50 ml). The aqueous layer was extracted again with chloroform (50 ml). The combined organic extracts were then dried over sodium sulphate and concentrated in vacuo (20° C.; 14 mmHg) to give a crude oil which was purified by flash chromatography over silica gel eluting with ethyl acetate to give (±)-N-methyl-2-oxo-1-(quinolin-3-yl)cyclohexanecarbothioamide (0.1 g, 0.33 mmol), m.p. 235°-236° C.;

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