Benzothiazole → 2-[benzothiazol-2(3H)-ylidene]-2-(pyrimidin-2-yl)acetamide

HRID 1091624Notes

Reaction equation

HRID 1091624 reaction equation
[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[CH:2]1.[N:10]1[CH:15]=[CH:14][CH:13]=[N:12][C:11]=1[CH2:16][C:17]#[N:18].[N:19]1[CH:24]=[CH:23][CH:22]=[N:21][C:20]=1[CH2:25][C:26]([NH2:28])=[O:27].[H-].[Na+]>O1CCCC1>[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[NH:3][C:2]1=[C:16]([C:11]1[N:12]=[CH:13][CH:14]=[CH:15][N:10]=1)[C:17]#[N:18].[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[NH:3][C:2]1=[C:25]([C:20]1[N:21]=[CH:22][CH:23]=[CH:24][N:19]=1)[C:26]([NH2:28])=[O:27]

Participants

7

Reactant 4

HCID 7222BenzothiazoleHCID 24758Sodium hydrideHCID 15264944(Pyrimidin-2-yl)acetonitrileHCID 534076612-(Pyrimidin-2-yl)acetamide

Product 2

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In this synthesis, the benzothiazole 10 [L is a leaving group] is coupled with a 2-(pyrimidin-2-yl)acetonitrile 11 or 2-(pyrimidin-2-yl)acetamide 12 in the presence of a strong base, such as sodium hydride, in an aprotic polar solvent, such as tetrahydrofuran, 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 this synthesis

Sources & evidence

ORD record
ord-9493443541344b6fb10ea041349d7d40
Source dataset
uspto-grants-2012_03
Patent number
US08129396B2

Reaction notes

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