Guanidine → 2-(4-Ethyl-7-methyl-benzo[b]thiophen-5-yloxy)-3-phenylamino-acrylonitrile

HRID 2266173

Reaktionsgleichung

Reaktionsgleichung von HRID 2266173
CN(C)[CH:3]([N:20]([CH3:22])C)[CH:4]([O:7][C:8]1[CH:16]=[C:15]([CH3:17])[C:11]2[S:12][CH:13]=[CH:14][C:10]=2[C:9]=1[CH2:18][CH3:19])[C:5]#[N:6].Cl.N[C:26]1[CH:31]=[CH:30]C=[CH:28][CH:27]=1.Cl.NC(N)=N.C[O-].[Na+].NC(N)=N>C(O)C>[CH2:18]([C:9]1[C:10]2[CH:14]=[CH:13][S:12][C:11]=2[C:15]([CH3:17])=[CH:16][C:8]=1[O:7][C:4](=[CH:3][NH:20][C:22]1[CH:30]=[CH:31][CH:26]=[CH:27][CH:28]=1)[C:5]#[N:6])[CH3:19]

Komponenten

7

Edukt 5

HCID 3520GuanidineHCID 5742Guanidine HydrochlorideHCID 8870Benzenamine hydrochloride (1:1)HCID 10942334Sodium MethoxideHCID 595987063,3-Bis-dimethylamino-2-(4-ethyl-7-methyl-benzo[b]thiophen-5-yloxy)-propionitrile

Produkt 1

HCID 670534132-(4-Ethyl-7-methyl-benzo[b]thiophen-5-yloxy)-3-phenylamino-acrylonitrileAusbeute 55 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel2×

Versuchsvorschrift

3,3-Bis-dimethylamino-2-(4-ethyl-7-methyl-benzo[b]thiophen-5-yloxy)-propionitrile (590 mg, 2 mmol) and aniline HCl (1.1 g, 9 mmol) in 5 mL absolute ethanol were heated at reflux for 2.0 hours. In a separate flask, guanidine HCl (0.850 mg., 9 mmol) and sodium methoxide solution (1.83 ml, 9 mmol, 4.9 molar solution in methanol) were mixed in 1 ml Ethanol. The guanidine solution was added to the reaction mixture via pipette, and the reaction mixture was heated to reflux for 5 hours, then cooled. Solvent was removed in vacuo, and the residue was, chromatographed (5% MeOH/methylene chloride/1% NH4OH) to give 368 mg 2-(4-Ethyl-7-methyl-benzo[b]thiophen-5-yloxy)-3-phenylamino-acrylonitrile, 61% . Also present was 50 mg of 5-(4-Ethyl-7-methyl-benzo[b]thiophen-5-yloxy)-pyrimidine-2,4-diamine, 9% .

Aufarbeitung

  1. temperatureat reflux for 2.0 hours
  2. temperaturethe reaction mixture was heated
  3. temperatureto reflux for 5 hours
  4. temperaturecooled
  5. customSolvent was removed in vacuo
  6. customchromatographed (5% MeOH/methylene chloride/1% NH4OH)

Quellen und Nachweise

ORD-Eintrag
ord-be70946a32c14a1d84e5306eb9712a78
Quelldatensatz
uspto-grants-2010_12
Patentnummer
US07858632B2

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