O-Phenylenediamine → 2-[1H-benzimidazol-2(3H)-ylidene]-2-(pyrimidin-2-yl)acetonitrile

HRID 1091623Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1091623
[C:1]1([NH2:8])[C:2]([NH2:7])=[CH:3][CH:4]=[CH:5][CH:6]=1.CS[C:11]([S:21][CH3:22])=[C:12]([C:15]1[N:20]=[CH:19][CH:18]=[CH:17][N:16]=1)[C:13]#[N:14]>>[NH:7]1[C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][C:1]=2[NH:8][C:11]1=[C:12]([C:15]1[N:20]=[CH:19][CH:18]=[CH:17][N:16]=1)[C:13]#[N:14].[S:21]1[C:22]2[CH:4]=[CH:5][CH:6]=[CH:1][C:2]=2[NH:7][C:11]1=[C:12]([C:15]1[N:20]=[CH:19][CH:18]=[CH:17][N:16]=1)[C:13]#[N:14]

Komponenten

4

Edukt 2

HCID 7243O-Phenylenediamine2×HCID 592682083,3-Bis(methylthio)-2-(pyrimidin-2-yl)acrylonitrile

Produkt 2

HCID 665932562-[1H-benzimidazol-2(3H)-ylidene]-2-(pyrimidin-2-yl)acetonitrileHCID 66593501HCID 66593501, Verbindung

Versuchsvorschrift

In the first step of the synthesis, a benzene-1,2-diamine (1, X═NH) or 2-aminothiophenol (1, X═S) is coupled with a 3,3-bis(methylthio)-2-(pyrimidin-2-yl)acrylonitrile 9 to give a 2-[1H-benzimidazol-2(3H)-ylidene]-2-(pyrimidin-2-yl)acetonitrile or 2-[benzothiazol-2(3H)-ylidene]-2-(pyrimidin-2-yl)acetonitrile 6. The reaction is carried out under generally the same conditions as are used in the first step of the first half of Reaction Scheme 1. In the second step, the compound of formula 6 is hydrolyzed to a 2-[1H-benzimidazol-2(3H)-ylidene]-2-(pyrimidin-2-yl)acetamide or 2-[benzothiazol-2(3H)-ylidene]-2-(pyrimidin-2-yl)acetamide 8, as in Reaction Scheme 1.

Aufarbeitung

  1. customIn the first step of the synthesis

Quellen und Nachweise

ORD-Eintrag
ord-3c716cd7d49e4fd8946d26b4e248cd3e
Quelldatensatz
uspto-grants-2012_03
Patentnummer
US08129396B2

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