Acrylonitrile → HCID 57839027, Verbindung

HRID 732948Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 732948
[Cl:1][C:2]1[CH:16]=[C:15]([Cl:17])[CH:14]=[CH:13][C:3]=1[C:4]([C:6](=[CH:9]N(C)C)[C:7]#[N:8])=O.C(#N)C=C.Cl.[CH3:23][O:24][C:25]1[CH:26]=[C:27]([CH:31]=[C:32]([O:34][CH3:35])[CH:33]=1)[C:28]([NH2:30])=[NH:29].C[O-].[Na+]>CO>[Cl:1][C:2]1[CH:16]=[C:15]([Cl:17])[CH:14]=[CH:13][C:3]=1[C:4]1[C:6]([C:7]#[N:8])=[CH:9][N:30]=[C:28]([C:27]2[CH:31]=[C:32]([O:34][CH3:35])[CH:33]=[C:25]([O:24][CH3:23])[CH:26]=2)[N:29]=1

Komponenten

6

Edukt 4

HCID 7855AcrylonitrileHCID 10942334Sodium Methoxide2×HCID 123012433,5-Dimethoxy-benzamidine hydrochlorideHCID 533953932-(2,4-Dichlorobenzoyl)-3-(dimethylamino)prop-2-enenitrile

Produkt 1

HCID 57839027HCID 57839027, VerbindungAusbeute 38,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

To a stirred solution of Step 2 acrylonitrile (1.5 g, 5.6 mmol) and 3,5-dimethoxybenzamidine hydrochloride (1.2 g, 5.6 mmol) in MeOH (30 mL) was added NaOMe (25% in MeOH, 2.56 mL, 11.2 mmol). The reaction was heated to reflux for 5 hr. Additional NaOMe (25% in MeOH, 2.56 mL, 11.2 mmol) was added and was kept for 16 hr. The reaction was cooled to ambient temperature and quenched by addition of H2O (50 mL). The reaction was filtered and the solid was washed with MeOH (40 mL) to give 4-(2,4-dichlorophenyl)-2-(3,5-dimethoxyphenyl)pyrimidine-5-carbonitrile (960 mg, 38.4%) as a white solid.

Aufarbeitung

  1. temperatureThe reaction was heated
  2. temperatureto reflux for 5 hr
  3. customquenched by addition of H2O (50 mL)
  4. filtrationThe reaction was filtered
  5. washthe solid was washed with MeOH (40 mL)

Quellen und Nachweise

ORD-Eintrag
ord-f10b3ffa47a0438db377645a30483120
Quelldatensatz
uspto-grants-2009_09
Patentnummer
US07589088B2

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