Potassium Carbonate → 1-{4-[2-(2-Mercapto-ethylthio)-ethylthio]-phenyl}-2-methyl-2-morpholin-4-yl-propan-1-one

HRID 376969

Reaktionsgleichung

Reaktionsgleichung von HRID 376969
[SH:1][CH2:2][CH2:3][S:4][CH2:5][CH2:6][SH:7].C(=O)([O-])[O-].[K+].[K+].Cl[C:15]1[CH:20]=[CH:19][C:18]([C:21](=[O:31])[C:22]([CH3:30])([N:24]2[CH2:29][CH2:28][O:27][CH2:26][CH2:25]2)[CH3:23])=[CH:17][CH:16]=1>CC(N(C)C)=O.C(OCC)(=O)C>[SH:1][CH2:2][CH2:3][S:4][CH2:5][CH2:6][S:7][C:15]1[CH:16]=[CH:17][C:18]([C:21](=[O:31])[C:22]([CH3:23])([N:24]2[CH2:25][CH2:26][O:27][CH2:28][CH2:29]2)[CH3:30])=[CH:19][CH:20]=1

Komponenten

6

Edukt 3

HCID 11430Potassium CarbonateHCID 77117Bis(2-mercaptoethyl) sulfideHCID 157024081-(4-Chlorophenyl)-2-methyl-2-(morpholin-4-yl)propan-1-one

Produkt 1

HCID 193605981-{4-[2-(2-Mercapto-ethylthio)-ethylthio]-phenyl}-2-methyl-2-morpholin-4-yl-propan-1-one

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8857Ethyl AcetateLösungsmittelHCID 31374DimethylacetamideLösungsmittel2×

Versuchsvorschrift

25.7 g (0.15 mol) of 2-mercaptoethylsulfide (purity 90%) are added to a suspension of 8.3 g (0.06 mol) of potassium carbonate in 50 ml of dimethylacetamide. A solution of 8.0 g (0.03 mol) 1-(4-chlorophenyl)-2-methyl-2-morpholin-4-yl-propan-1-one in 25 ml of dimethylacetamide is added dropwise at 85° C. over 60 min. After stirring for 5 h, the reaction mixture is cooled, diluted with ethyl acetate (100 ml), extracted with water (3×100 ml) to remove the carbonate and dimethylacetamide, dried over MgSO4, and concentrated under vacuum. The resulting yellow liquid (stench) is purified by flash chromatography on silica gel (hexane/ethyl acetate 85:15) to yield a pale yellow oil. The structure is confirmed by the 1H-NMR spectrum (CDCl3): δ [ppm] 1.31 (s, 6H), 1.750 (t, SH), 2.57 (t, 4H), 2.71-2.85 (m, 6H), 3.20 (t, 2H), 3.70 (t, 4), 7.31 (d, 2H), 8.51 (d, 2H).

Aufarbeitung

  1. temperaturethe reaction mixture is cooled
  2. extractionextracted with water (3×100 ml)
  3. customto remove the carbonate and dimethylacetamide
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated under vacuum
  6. customThe resulting yellow liquid (stench) is purified by flash chromatography on silica gel (hexane/ethyl acetate 85:15)
  7. customto yield a pale yellow oil

Quellen und Nachweise

ORD-Eintrag
ord-5a894777c9394086a3dbd3e0cd1bc86f
Quelldatensatz
uspto-grants-2000_02
Patentnummer
US06022906

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