3-(phenylamino)-2-(pyrimidin-2(1H)-ylidene)-3-thioxo-propionitrile → 2-[benzothiazol-2(3H)-ylidene]-2-(pyrimidin-2-yl)acetamide

HRID 1091626Notes

Reaction equation

HRID 1091626 reaction equation
[C:1]1([NH:7][C:8](=[S:18])[C:9](=[C:12]2[N:17]=[CH:16][CH:15]=[CH:14][NH:13]2)[C:10]#[N:11])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.BrBr.C(O)(=[O:23])C>[Fe-3](C#N)(C#N)(C#N)(C#N)(C#N)C#N.[K+].[K+].[K+]>[S:18]1[C:6]2[CH:5]=[CH:4][CH:3]=[CH:2][C:1]=2[NH:7][C:8]1=[C:9]([C:12]1[N:13]=[CH:14][CH:15]=[CH:16][N:17]=1)[C:10]#[N:11].[S:18]1[C:6]2[CH:5]=[CH:4][CH:3]=[CH:2][C:1]=2[NH:7][C:8]1=[C:9]([C:12]1[N:13]=[CH:14][CH:15]=[CH:16][N:17]=1)[C:10]([NH2:11])=[O:23]

Participants

5

Reactant 2

HCID 866405133-(phenylamino)-2-(pyrimidin-2(1H)-ylidene)-3-thioxo-propionitrileHCID 87433071bromine AcOH

Product 2

HCID 665933542-[benzothiazol-2(3H)-ylidene]-2-(pyrimidin-2-yl)acetamideHCID 66593501HCID 66593501, compound

Reagents, catalysts & solvents 1

HCID 178511488HCID 178511488, compoundCatalyst

Procedure

In the first step of the synthesis, the phenyl isothiocyanate 14 (which may be readily prepared by reaction of an aniline with thiophosgene) is coupled with a 2-(pyrimidin-2-yl)acetonitrile 11 or 2-(pyrimidin-2-yl)acetamide 12 in the presence of a base to give a 3-(phenylamino)-2-(pyrimidin-2(1H)-ylidene)-3-thioxo-propionitrile 15 or 3-(phenylamino)-2-(pyrimidin-2-yl)-3-thioxopropanamide 16. In the second step, ring closure of the compound of formula 15 or 16 is achieved by reaction with an agent such as bromine/acetic acid or potassium ferricyanide, to give a 2-[benzothiazol-2(3H)-ylidene]-2-(pyrimidin-2-yl)acetonitrile 6 or 2-[benzothiazol-2(3H)-ylidene]-2-(pyrimidin-2-yl)acetamide 8. If the compound of formula 6 has been prepared, it is then hydrolyzed to a compound of formula 8, as in Reaction Scheme 1.

Sources & evidence

ORD record
ord-02e087d21181402c91e0664031d80502
Source dataset
uspto-grants-2012_03
Patent number
US08129396B2

Reaction notes

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