Aniline → 3-(phenylamino)-2-(pyrimidin-2(1H)-ylidene)-3-thioxo-propionitrile

HRID 1091625Notes

Reaction equation

HRID 1091625 reaction equation
[C:1]1([N:7]=[C:8]=[S:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.NC1C=CC=CC=1.C(Cl)(Cl)=S.[N:21]1[CH:26]=[CH:25][CH:24]=[N:23][C:22]=1[CH2:27][C:28]#[N:29].[N:30]1[CH:35]=[CH:34][CH:33]=[N:32][C:31]=1[CH2:36][C:37]([NH2:39])=[O:38]>>[C:1]1([NH:7][C:8](=[S:9])[C:27](=[C:22]2[N:21]=[CH:26][CH:25]=[CH:24][NH:23]2)[C:28]#[N:29])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:1]1([NH:7][C:8](=[S:9])[CH:36]([C:31]2[N:32]=[CH:33][CH:34]=[CH:35][N:30]=2)[C:37]([NH2:39])=[O:38])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

7

Reactant 5

HCID 6115AnilineHCID 7673Phenyl IsothiocyanateHCID 10040ThiophosgeneHCID 15264944(Pyrimidin-2-yl)acetonitrileHCID 534076612-(Pyrimidin-2-yl)acetamide

Product 2

HCID 866405133-(phenylamino)-2-(pyrimidin-2(1H)-ylidene)-3-thioxo-propionitrileHCID 866405143-(Phenylamino)-2-(pyrimidin-2-yl)-3-thioxopropanamide

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.

Workup

  1. customIn the first step of the synthesis

Sources & evidence

ORD record
ord-5b6990f9cb814da9952743b7300e2a3a
Source dataset
uspto-grants-2012_03
Patent number
US08129396B2

Reaction notes

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