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Methylamine → 4-Chloro-2-[4-(methylamino)-1-(3-thienyl)butoxy]benzonitrile oxalate

HRID 352126
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 352126
[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[C:4]([O:10][CH:11]([C:16]2[CH:20]=[CH:19][S:18][CH:17]=2)[CH2:12][CH2:13][CH2:14][OH:15])[CH:3]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.I[N:41]1C(=[O:46])CC[C:42]1=O.CN.[C:50](=[O:53])([OH:52])[O-].[Na+]>O1CCCC1>[C:14]([OH:15])(=[O:46])[C:50]([OH:52])=[O:53].[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[C:4]([O:10][CH:11]([C:16]2[CH:20]=[CH:19][S:18][CH:17]=2)[CH2:12][CH2:13][CH2:14][NH:41][CH3:42])[CH:3]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 5

HCID 6329MethylamineHCID 11776TriphenylphosphineHCID 120273N-IodosuccinimideHCID 516892Sodium BicarbonateHCID 227151874-Chloro-2-[4-hydroxy-1-(3-thienyl)butoxy]benzonitrile

Produkt 1

HCID 227151454-Chloro-2-[4-(methylamino)-1-(3-thienyl)butoxy]benzonitrile oxalate
Ausbeute 37 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

The product from step (d) (0.38 g, 1.23 mmol) was dissolved in anhydrous tetrahydrofuran (100 ml) and triphenylphosphine (1.062 g, 4.05 mmol) added. The solution was cooled to 0° C. and N-iodosuccinimide (0.912 g, 4.05 mmol) added. The reaction was allowed to warm to room temperature overnight, whilst stirring. Methylamine, as a 40% aqueous solution, (5 ml) was added and the reaction stirred for 24 h. Saturated aqueous sodium bicarbonate solution (40 ml) was added and the mixture extracted with ethyl acetate (3×70 ml). The combined extracts were washed with water (20 ml), dried (magnesium sulphate) and evaporated in vacuo. The residue was dissolved in methanol and applied to CC SCX resin. The resin was washed with methanol (200 ml) and the product liberated with 7N ammonia in methanol (100 ml). The solvent was removed in vacuo and the product converted into an oxalate salt and recrystallised from ethanol to give the title compound as a white solid (0.185 g, 37%).

Aufarbeitung

  1. temperatureto warm to room temperature overnight
  2. stirringthe reaction stirred for 24 h
  3. extractionthe mixture extracted with ethyl acetate (3×70 ml)
  4. washThe combined extracts were washed with water (20 ml)
  5. dry with materialdried (magnesium sulphate)
  6. customevaporated in vacuo
  7. dissolutionThe residue was dissolved in methanol
  8. washThe resin was washed with methanol (200 ml)
  9. customThe solvent was removed in vacuo
  10. customrecrystallised from ethanol

Quellen und Nachweise

ORD-Eintrag
ord-6a5f9a3585304f5093a2284364ee2add
Quelldatensatz
uspto-grants-2004_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06743939B2

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