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

HRID 1091664Notes

Reaction equation

HRID 1091664 reaction equation
[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[NH:3][C:2]1=[C:10]([C:13]1[N:18]=[CH:17][CH:16]=[CH:15][N:14]=1)[C:11]#[N:12].[OH-:19].[Na+]>S(=O)(=O)(O)O>[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[NH:3][C:2]1=[C:10]([C:13]1[N:14]=[CH:15][CH:16]=[CH:17][N:18]=1)[C:11]([NH2:12])=[O:19]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 66593501HCID 66593501, compound

Product 1

HCID 665933542-[benzothiazol-2(3H)-ylidene]-2-(pyrimidin-2-yl)acetamideYield 40%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

2-[Benzothiazol-2(3H)-ylidene]-2-(pyrimidin-2-yl)acetonitrile (0.1 g, 0.39 mmol) was dissolved in concentrated sulfuric acid (2 mL) and stirred at room temperature for 5 hr. The mixture was cooled to 0° C., poured over ice, and neutralized with 50% aqueous sodium hydroxide. The precipitate that formed was collected by filtration and purified by reverse phase preparative HPLC to give 2-[benzothiazol-2(3H)-ylidene]-2-(pyrimidin-2-yl)acetamide (42 mg, 40% yield) as a yellow solid.

Workup

  1. temperatureThe mixture was cooled to 0° C.
  2. additionpoured over ice
  3. customThe precipitate that formed
  4. filtrationwas collected by filtration
  5. custompurified by reverse phase preparative HPLC

Sources & evidence

ORD record
ord-abb47f7e7e4341318753fd42aa9fb1af
Source dataset
uspto-grants-2012_03
Patent number
US08129396B2

Reaction notes

Loading…