Water → HCID 45256305, compound

HRID 1091662Notes

Reaction equation

HRID 1091662 reaction equation
C(OC([N:8]1[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[NH:10][C:9]1=[C:17]([C:20]1[N:25]=[C:24]([C:26]([F:29])([F:28])[F:27])[CH:23]=[CH:22][N:21]=1)[C:18]#[N:19])=O)(C)(C)C.[OH-:30].[Na+].O>S(=O)(=O)(O)O>[NH:8]1[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[NH:10][C:9]1=[C:17]([C:20]1[N:25]=[C:24]([C:26]([F:27])([F:28])[F:29])[CH:23]=[CH:22][N:21]=1)[C:18]([NH2:19])=[O:30]

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 66593539HCID 66593539, compound

Product 1

HCID 45256305HCID 45256305, compoundYield 18%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

2-[1-(tert-Butoxycarbonyl)benzimidazol-2(3H)-ylidene]-2-(4-trifluoromethylpyrimidin-2-yl)-acetonitrile (8.1 g, 20 mmol) was dissolved in concentrated sulfuric acid (30 mL), and the solution added gradually to ice/water (100 mL), allowed to warm to room temperature, and stirred overnight. The mixture was cooled to 0° C., poured over ice, and neutralized with 50% aqueous sodium hydroxide. Water was added, and the crude product was extracted with 4:1 chloroform/isopropanol. The organic phase was dried over magnesium sulfate, the solvent was removed under vacuum, and the solid was purified by reverse phase preparative HPLC to give 2-[1H-benzimidazol-2(3H)-ylidene]-2-(4-trifluoromethylpyrimidin-2-yl)acetamide (1.18 g, 18% overall yield) as a yellow solid.

Workup

  1. temperatureThe mixture was cooled to 0° C.
  2. additionpoured over ice
  3. extractionthe crude product was extracted with 4:1 chloroform/isopropanol
  4. dry with materialThe organic phase was dried over magnesium sulfate
  5. customthe solvent was removed under vacuum
  6. customthe solid was purified by reverse phase preparative HPLC

Sources & evidence

ORD record
ord-43b23f02eb9942fca8496e2c5d79f20d
Source dataset
uspto-grants-2012_03
Patent number
US08129396B2

Reaction notes

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