Thiophenol → N-(2-(1,1-dioxido-4-thiomorpholinyl)ethyl)-3-methoxy-1-propanamine

HRID 85566Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 85566
[O:1]=[S:2]1(=[O:28])[CH2:7][CH2:6][N:5]([CH2:8][CH2:9][N:10]([CH2:23][CH2:24][CH2:25][O:26][CH3:27])S(C2C=CC=CC=2[N+]([O-])=O)(=O)=O)[CH2:4][CH2:3]1.C1(S)C=CC=CC=1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C.C(OCC)(=O)C>[O:28]=[S:2]1(=[O:1])[CH2:3][CH2:4][N:5]([CH2:8][CH2:9][NH:10][CH2:23][CH2:24][CH2:25][O:26][CH3:27])[CH2:6][CH2:7]1

Komponenten

6

Edukt 3

HCID 7969ThiophenolHCID 11430Potassium CarbonateHCID 68358023N-(2-(1,1-dioxido-4-thiomorpholinyl)ethyl)-N-(3-methoxypropyl)-2-nitrobenzenesulfonamide

Produkt 1

HCID 62561927N-(2-(1,1-dioxido-4-thiomorpholinyl)ethyl)-3-methoxy-1-propanamineAusbeute 87,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6342AcetonitrileLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

N-(2-(1,1-dioxido-4-thiomorpholinyl)ethyl)-N-(3-methoxypropyl)-2-nitrobenzenesulfonamide (0.510 g, 1.17 mmol) and thiophenol (0.387 g, 3.51 mmol) were combined in dry acetonitrile (10 mL). Potassium carbonate (0.647 g, 4.68 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 a yellow oil (0.255 g, 87% yield). No further purification was performed and the mixture was carried forward to the next step. LCMS: m/z 251 (M+H+), 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 1.77 (quin, J=6.53 Hz, 2H) 2.13 (br. s., 2H) 2.62-2.68 (m, 2H) 2.68-2.75 (m, 4H) 2.93-3.11 (m, 8H) 3.32 (s, 3H) 3.44 (t, J=6.15 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-63c9340ed26b4047916768ab37731d84
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08846647B2

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