Morpholine → HCID 83074581, Verbindung

HRID 1479828

Reaktionsgleichung

Reaktionsgleichung von HRID 1479828
Cl[C:2]1[CH:7]=[C:6]([C:8]#[N:9])[CH:5]=[C:4]([Cl:10])[N:3]=1.[NH:11]1[CH2:16][CH2:15][O:14][CH2:13][CH2:12]1.FC1C=CC(S(N(CC)C(=C)C(NCC2C=CN=C(C3C=CC(OC(F)(F)F)=CC=3)C=2)=O)(=O)=O)=CC=1>C(O)C.ClC1SC(S(N(CC)C(=C)C(NCC2C=CN=C(C3C=CC(OC(F)(F)F)=CC=3)C=2)=O)(=O)=O)=CC=1>[Cl:10][C:4]1[CH:5]=[C:6]([C:8]#[N:9])[CH:7]=[C:2]([N:11]2[CH2:16][CH2:15][O:14][CH2:13][CH2:12]2)[N:3]=1

Komponenten

6

Edukt 3

HCID 8083MorpholineHCID 7359062,6-DichloroisonicotinonitrileHCID 78319909HCID 78319909, Verbindung

Produkt 1

HCID 83074581HCID 83074581, VerbindungAusbeute 89 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 78319913HCID 78319913, VerbindungLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

2,6-dichloropyridine-4-carbonitrile 24 (4 gr, 23.13 mmol) was dissolved in 100 ml of ethanol. To the solution were added TEA (1 equiv., 3.22 ml), morpholine (1 equiv., 2 ml) and the mixture was stirred at 70° C. for 4 hours. (TLC AcOEt 3/petroleum ether 7). The solvent was evaporated and the residue was dissolved with ethyl acetate, washed with water and brine. The organic phase was dried over sodium sulfate and concentrated under vacuum. The crude was crystallized from ethyl acetate and petroleum ether to give a beige solid. (4.6 g, 89% yield) 1HNMR (DMSO, 400 MHz) δ 3.58 (4H, m), 3.64 (4H, m), 7.10 (1H, s), 7.32 (1H, s)

Aufarbeitung

  1. customThe solvent was evaporated
  2. dissolutionthe residue was dissolved with ethyl acetate
  3. washwashed with water and brine
  4. dry with materialThe organic phase was dried over sodium sulfate
  5. concentrationconcentrated under vacuum
  6. customThe crude was crystallized from ethyl acetate and petroleum ether
  7. customto give a beige solid

Quellen und Nachweise

ORD-Eintrag
ord-aa930a730be148839c0def30ec789bd8
Quelldatensatz
uspto-grants-2016_08
Patentnummer
US09409864B2

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