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Iodoethane → HCID 56598655, Verbindung

HRID 72655
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 72655
[H-].[Na+].[CH3:3][O:4][C:5]1[C:10]([NH:11][C:12](=[O:14])[CH3:13])=[CH:9][C:8]([CH2:15][S:16](/[CH:19]=[CH:20]/[C:21]2[C:26]([O:27][CH3:28])=[CH:25][C:24]([O:29][CH3:30])=[CH:23][C:22]=2[O:31][CH3:32])(=[O:18])=[O:17])=[CH:7][N:6]=1.I[CH2:34][CH3:35]>C1COCC1>[CH2:34]([N:11]([C:10]1[C:5]([O:4][CH3:3])=[N:6][CH:7]=[C:8]([CH2:15][S:16](/[CH:19]=[CH:20]/[C:21]2[C:26]([O:27][CH3:28])=[CH:25][C:24]([O:29][CH3:30])=[CH:23][C:22]=2[O:31][CH3:32])(=[O:18])=[O:17])[CH:9]=1)[C:12](=[O:14])[CH3:13])[CH3:35]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 6340IodoethaneHCID 24758Sodium hydrideHCID 86690903(E)-N-(2-methoxy-5-((2,4,6-trimethoxystyrylsulfonyl)methyl)pyridin-3-yl)acetamide

Produkt 1

HCID 56598655HCID 56598655, VerbindungAusbeute 75 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Sodium hydride (0.6 mg, 0.025 mmol) was added into the solution of (E)-N-(2-methoxy-5-((2,4,6-trimethoxystyrylsulfonyl)methyl)pyridin-3-yl)acetamide (10 mg, 0.023 mmol) in dry THF (5 mL). The mixture was stirred at room temperature for 45 min. Iodoethane (15 μL, 0.05 mmol) was added dropwise into the mixture and stirred at room temperature for another 2 h. After evaporated to dryness, the residue was diluted with H2O (10 mL) and extracted (2×20 mL CH2Cl2). The combined extracts were extracted with sat. Na2CO3, washed with brine, dried on MgSO4, and filtered. The residue was purified by silica gel chromatography, eluting with PE/EtOAc (1:1, v/v) to afford pure product as a white powder (8 mg, 75%). 1H-NMR (CDCl3): δ 1.02 (t, 3H, J=7.2 Hz, CH3), 1.74 (s, 3H, CH3), 3.42 (m, 2H, CH2), 3.86 (s, 6H, 2×OCH3), 3.87 (s, 3H, OCH3), 3.99 (s, 3H, OCH3), 4.23 (s, 2H, CH2), 6.10 (s, 2H, Ph-H), 7.07 (d, 1H, J=15.6 Hz, CH), 7.05 (d, 1H, J=2.0 Hz, Py-H), 7.77 (d, 1H, J=15.6 Hz, CH), 8.15 (d, 1H, J=2.0 Hz, Py-H); HR-MS (ESI+) m/z: 465.1762 [M+H]+, C22H28N2O7S, requires 464.1617.

Aufarbeitung

  1. stirringstirred at room temperature for another 2 h
  2. customAfter evaporated to dryness
  3. additionthe residue was diluted with H2O (10 mL)
  4. extractionextracted (2×20 mL CH2Cl2)
  5. extractionThe combined extracts were extracted with sat. Na2CO3
  6. washwashed with brine
  7. customdried on MgSO4
  8. filtrationfiltered
  9. customThe residue was purified by silica gel chromatography
  10. washeluting with PE/EtOAc (1:1

Quellen und Nachweise

ORD-Eintrag
ord-8722af966ee645ff8819628d69696677
Quelldatensatz
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08829003B2

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