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

HRID 1091623Notes

Reaction equation

HRID 1091623 reaction equation
[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]

Participants

4

Reactant 2

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

Product 2

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

Procedure

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.

Workup

  1. customIn the first step of the synthesis

Sources & evidence

ORD record
ord-3c716cd7d49e4fd8946d26b4e248cd3e
Source dataset
uspto-grants-2012_03
Patent number
US08129396B2

Reaction notes

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