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Methyl isothiocyanate → (+/-)-N-methyl-2-oxo-1-(3-quinolinyl)cyclohexanecarbothioamide

HRID 5909
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 5909
[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]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 11167Methyl isothiocyanateHCID 19794569(+/-)-2-(3-Quinolinyl)cyclohexanoneHCID 23665647Potassium tert-butoxide

Produkt 1

HCID 19794596(+/-)-N-methyl-2-oxo-1-(3-quinolinyl)cyclohexanecarbothioamideAusbeute 9,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

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.;

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-437552d324044abea55731a4552ead93
Quelldatensatz
uspto-grants-1993_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05246950

Notizen zur Reaktion

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