StartseiteMCPWorkbenchSkills
StartseiteWorkbenchBenachrichtigungenMein Bereich
llms.txt · MCP-AnleitungDatenschutz · Nutzungsbedingungen · Supportv1.8.0
  1. Startseite
  2. /Reaktion

Thiophenol → 3-((tert-butyl(dimethyl)silyl)oxy)-N-(2-(1,1-dioxido-4-thiomorpholinyl)ethyl)-1-propanamine

HRID 85562
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 85562
[Si:1]([O:8][CH2:9][CH2:10][CH2:11][N:12]([CH2:25][CH2:26][N:27]1[CH2:32][CH2:31][S:30](=[O:34])(=[O:33])[CH2:29][CH2:28]1)S(C1C=CC=CC=1[N+]([O-])=O)(=O)=O)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].C1(S)C=CC=CC=1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C.C(OCC)(=O)C>[Si:1]([O:8][CH2:9][CH2:10][CH2:11][NH:12][CH2:25][CH2:26][N:27]1[CH2:28][CH2:29][S:30](=[O:34])(=[O:33])[CH2:31][CH2:32]1)([C:4]([CH3:7])([CH3:5])[CH3:6])([CH3:3])[CH3:2]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 3

HCID 7969ThiophenolHCID 11430Potassium CarbonateHCID 68275979N-(3-((tert-butyl(dimethyl)silyl)oxy)propyl)-N-(2-(1,1-dioxido-4-thiomorpholinyl)ethyl)-2-nitrobenzenesulfonamide

Produkt 1

HCID 682759693-((tert-butyl(dimethyl)silyl)oxy)-N-(2-(1,1-dioxido-4-thiomorpholinyl)ethyl)-1-propanamineAusbeute 83 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6342
Acetonitrile
Lösungsmittel
HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

N-(3-((tert-butyl(dimethyl)silyl)oxy)propyl)-N-(2-(1,1-dioxido-4-thiomorpholinyl)ethyl)-2-nitrobenzenesulfonamide (0.540 g, 1.01 mmol) and thiophenol (0.333 g, 3.02 mmol) were combined in dry acetonitrile (10 mL). Potassium carbonate (0.557 g, 4.03 mmol) was added and the mixture was stirred at rt for 18 h. The mixture was diluted with ethyl acetate and filtered to remove unwanted solids. The crude filtrate was concentrated in vacuo, redissolved in methanol, and loaded onto a strong cation exchange resin cartridge to capture the desired product. Undesired materials were eluted from the cartridge with methanol, and then the desired material was released from the resin by elution with 2M ammonia in methanol. Concentration in vacuo gave the title compound as a yellow oil (0.294 g, 83% yield). No further purification was performed and the mixture was carried forward to the next step. LCMS: m/z 351 (M+H+), 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 0.06 (s, 6H) 0.90 (s, 9H) 1.75 (quin, J=6.46 Hz, 2H) 2.69-2.72 (m, 2H) 2.72-2.80 (m, 4H) 3.00-3.11 (m, 8H) 3.70 (t, J=6.02 Hz, 2H).

Aufarbeitung

  1. filtrationfiltered
  2. customto remove unwanted solids
  3. concentrationThe crude filtrate was concentrated in vacuo
  4. dissolutionredissolved in methanol
  5. washUndesired materials were eluted from the cartridge with methanol
  6. washthe desired material was released from the resin by elution with 2M ammonia in methanol
  7. concentrationConcentration in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-88fdcf04cc75478c8f69c14513d441b0
Quelldatensatz
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08846647B2

Notizen zur Reaktion

Wird geladen…

Auf dieser SeiteKomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion