Acetonitrile → HCID 22592061, compound

HRID 746641Notes

Reaction equation

HRID 746641 reaction equation
C(=O)([O-])[O-].[K+].[K+].C(#N)C.Br[CH2:11][C:12]([NH:14][C:15]1[C:16]([S:24][CH3:25])=[N:17][C:18]([CH3:23])=[CH:19][C:20]=1[S:21][CH3:22])=[O:13].[SH:26][C:27]1[O:28][C:29]2[CH:35]=[CH:34][CH:33]=[CH:32][C:30]=2[N:31]=1>O>[O:28]1[C:29]2[CH:35]=[CH:34][CH:33]=[CH:32][C:30]=2[N:31]=[C:27]1[S:26][CH2:11][C:12]([NH:14][C:15]1[C:16]([S:24][CH3:25])=[N:17][C:18]([CH3:23])=[CH:19][C:20]=1[S:21][CH3:22])=[O:13]

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 11430Potassium CarbonateHCID 222471492-Bromo-N-(6-methyl-2,4-bis(methylthio)pyridin-3-yl)acetamideHCID 1784182821,3-benzoxazole-2-thiol

Product 1

HCID 22592061HCID 22592061, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Potassium carbonate (46 mg, 0.33 mmol) was added to an acetonitrile (5 ml) solution of this amide (96 mg, 0.3 mmol) and 2-mercaptobenzoxazole (45 mg, 0.3 mmol), and the mixture was stirred at room temperature for 90 minutes. The reaction mixture was diluted with water, and then extracted with ethyl acetate. The organic layer was washed with water and then with a saturated aqueous solution of sodium chloride, and dried over sodium sulfate. Subsequently, the solvent was distilled off, and the resulting crude product was purified through silica gel chromatography (silica gel 10 g, eluent—hexane:acetone=5:2) to obtain 88 mg (yield 75%) of the desired compound as a colorless crystal.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with water
  3. dry with materialwith a saturated aqueous solution of sodium chloride, and dried over sodium sulfate
  4. distillationSubsequently, the solvent was distilled off
  5. customthe resulting crude product was purified through silica gel chromatography (silica gel 10 g, eluent—hexane:acetone=5:2)

Sources & evidence

ORD record
ord-0fe5b721db9a4ba7a55f5877cd83ca8d
Source dataset
uspto-grants-2008_07
Patent number
US07393866B2

Reaction notes

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