反応式
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[C:3]([CH:11]2[CH2:16][CH2:15][CH2:14][CH2:13][C:12]2=[O:17])[CH:2]=1.CC(C)([O-])C.[K+].[CH3:24][N:25]=[C:26]=[S:27]>O1CCCC1>[CH3:24][NH:25][C:26]([C:11]1([C:3]2[CH:2]=[N:1][C:10]3[C:5]([CH:4]=2)=[CH:6][CH:7]=[CH:8][CH:9]=3)[CH2:16][CH2:15][CH2:14][CH2:13][C:12]1=[O:17])=[S:27]参加物
実験手順
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.;
後処理
- customAfter 4 hours at 0° C. the reaction mixture was partitioned between saturated aqueous ammonium chloride solution (50 ml) and chloroform (50 ml)
- extractionThe aqueous layer was extracted again with chloroform (50 ml)
- dry with materialThe combined organic extracts were then dried over sodium sulphate
- concentrationconcentrated in vacuo (20° C.; 14 mmHg)
- customto give a crude oil which
- customwas purified by flash chromatography over silica gel eluting with ethyl acetate
出典と根拠
- ORDレコード
- ord-437552d324044abea55731a4552ead93
- 出典データセット
- uspto-grants-1993_09
- 特許番号
- US05246950
関連ノート
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