Water → HCID 13472313, Verbindung

HRID 1248059

Reaktionsgleichung

Reaktionsgleichung von HRID 1248059
[CH2:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH:2]1[NH:10][CH2:11][C:12]([OH:14])=[O:13].[C:15]([S:23][CH2:24][CH:25]([CH3:29])[C:26](Cl)=[O:27])(=[O:22])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.O>CC(N(C)C)=O>[C:15]([S:23][CH2:24][CH:25]([CH3:29])[C:26]([N:10]([CH:2]1[CH2:3][C:4]2[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=2)[CH2:1]1)[CH2:11][C:12]([OH:14])=[O:13])=[O:27])(=[O:22])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Komponenten

5

Edukt 3

HCID 962WaterHCID 99901132-IndanylglycineHCID 12878433(1)-S-(3-Chloro-2-methyl-3-oxopropyl) benzenecarbothioate

Produkt 1

HCID 13472313HCID 13472313, VerbindungAusbeute 67,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 31374DimethylacetamideLösungsmittel

Versuchsvorschrift

N-(2-Indanyl)glycine (1.0 g) is suspended in 10 ml of dimethylacetamide, then 2.0 g of 3-benzoylthio-2-methylpropionyl chloride is added dropwise with stirring at room temperature, and thereafter stirring is continued at room temperature for 2 hours. The reaction mixture is poured into 100 ml of water, and extracted with 200 ml of ethyl acetate. The extract is washed with 20 ml of 10% hydrochloric acid and with water, and dried over anhydrous sodium sulfate. After ethyl acetate is distilled off under reduced pressure, the residue is subjected to silica gel column chromatography and eluted with acetone-benzene (1:9). The oil obtained is crystallized from an ethyl ether-petroleum ether mixture, to give 1.4 g of N-(3-benzoylthio-2-methylpropionyl)-N-(2-indanyl)glycine, colorless needles showing a melting point of 113°-115° C.

Aufarbeitung

  1. stirringstirring
  2. extractionextracted with 200 ml of ethyl acetate
  3. washThe extract is washed with 20 ml of 10% hydrochloric acid and with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationAfter ethyl acetate is distilled off under reduced pressure
  6. washeluted with acetone-benzene (1:9)
  7. customThe oil obtained
  8. customis crystallized from an ethyl ether-petroleum ether mixture

Quellen und Nachweise

ORD-Eintrag
ord-220f23adcc6d479d91fd0eea120ebba1
Quelldatensatz
uspto-grants-1985_06
Patentnummer
US04521607

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