Sodium Hydroxide → 2-[benzothiazol-2(3H)-ylidene]-2-[4-tert-butyl-6-(trifluoromethyl)pyrimidin-2-yl]acetamide

HRID 1091680Notes

Reaction equation

HRID 1091680 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]=[C:17]([C:19]([CH3:22])([CH3:21])[CH3:20])[CH:16]=[C:15]([C:23]([F:26])([F:25])[F:24])[N:14]=1)[C:11]#[N:12].[OH-:27].[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:18]=[C:17]([C:19]([CH3:21])([CH3:22])[CH3:20])[CH:16]=[C:15]([C:23]([F:24])([F:25])[F:26])[N:14]=1)[C:11]([NH2:12])=[O:27]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 665933712-[Benzothiazol-2(3H)-ylidene]-2-[4-tert-butyl-6-(trifluoromethyl)pyrimidin-2-yl]acetonitrile

Product 1

HCID 665933052-[benzothiazol-2(3H)-ylidene]-2-[4-tert-butyl-6-(trifluoromethyl)pyrimidin-2-yl]acetamide

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

2-[Benzothiazol-2(3H)-ylidene]-2-[4-tert-butyl-6-(trifluoromethyl)pyrimidin-2-yl]acetonitrile (150 mg, 0.39 mmol) was dissolved in concentrated sulfuric acid (1.5 mL) and stirred at room temperature overnight. The mixture was cooled to 0° C., poured over ice, and neutralized with 50% aqueous sodium hydroxide. The product was partially extracted into chloroform, and dried to a brown solid (57 mg), which was purified by reverse phase preparative HPLC to give 2-[benzothiazol-2(3H)-ylidene]-2-[4-tert-butyl-6-(trifluoromethyl)pyrimidin-2-yl]acetamide (13 mg) as a yellow solid.

Workup

  1. temperatureThe mixture was cooled to 0° C.
  2. additionpoured over ice
  3. extractionThe product was partially extracted into chloroform
  4. dry with materialdried to a brown solid (57 mg), which
  5. customwas purified by reverse phase preparative HPLC

Sources & evidence

ORD record
ord-737e1bb1a0294ef38b3e72aed09ce5cf
Source dataset
uspto-grants-2012_03
Patent number
US08129396B2

Reaction notes

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