Potassium Carbonate → 4-(2-mercapto-ethyl)-3,N,N-trimethyl-benzamide

HRID 1754905Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1754905
O.C(O)(=O)CC(CC(O)=O)(C(O)=O)O.C(=O)([O-])[O-].[K+].[K+].[CH3:21][C:22]1[CH:23]=[C:24]([CH:30]=[CH:31][C:32]=1[CH2:33][CH2:34][S:35][Si](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[C:25]([N:27]([CH3:29])[CH3:28])=[O:26]>CO>[SH:35][CH2:34][CH2:33][C:32]1[CH:31]=[CH:30][C:24]([C:25]([N:27]([CH3:28])[CH3:29])=[O:26])=[CH:23][C:22]=1[CH3:21]

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 222302-Hydroxy-1,2,3-propanetricarboxylic acid hydrate (1:1)HCID 866727583,N,N-trimethyl-4-(2-triphenylsilanylsulfanyl-ethyl)-benzamide

Produkt 1

HCID 866727594-(2-mercapto-ethyl)-3,N,N-trimethyl-benzamideAusbeute 99 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

Citric acid monohydrate (110 mg, 0.523 mmol) and potassium carbonate (52.8 mg, 0.382 mmol) were added to a solution of 3,N,N-trimethyl-4-(2-triphenylsilanylsulfanyl-ethyl)-benzamide (767 mg, 1.59 mmol) in MeOH (27 ml) at room temperature, and the mixture was stirred for one hour. The reaction mixture was concentrated under reduced pressure, and the residue was then dissolved in dichloromethane. The organic layer was washed with water, and then dried over MgSO4 and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (hexane/ethyl acetate=2/1) to give 4-(2-mercapto-ethyl)-3,N,N-trimethyl-benzamide (351 mg, 99%).

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. dissolutionthe residue was then dissolved in dichloromethane
  3. washThe organic layer was washed with water
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting residue was purified by silica gel column chromatography (hexane/ethyl acetate=2/1)

Quellen und Nachweise

ORD-Eintrag
ord-bc18df286931403eb7a34e78b47ac7c7
Quelldatensatz
uspto-grants-2015_10
Patentnummer
US09169254B2

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