Potassium Carbonate → HCID 11774461, compound

HRID 2219253Notes

Reaction equation

HRID 2219253 reaction equation
Br[CH2:2][CH2:3][CH2:4][C:5]([NH:7][C:8]1[C:9]([S:17][CH3:18])=[N:10][C:11]([CH3:16])=[CH:12][C:13]=1[S:14][CH3:15])=[O:6].[SH:19][C:20]1[O:21][C:22]2[CH:28]=[CH:27][CH:26]=[CH:25][C:23]=2[N:24]=1.C1OCCOCCOCCOCCOCCOC1.C(=O)([O-])[O-].[K+].[K+]>O.CN(C=O)C>[O:21]1[C:22]2[CH:28]=[CH:27][CH:26]=[CH:25][C:23]=2[N:24]=[C:20]1[S:19][CH2:2][CH2:3][CH2:4][C:5]([NH:7][C:8]1[C:9]([S:17][CH3:18])=[N:10][C:11]([CH3:16])=[CH:12][C:13]=1[S:14][CH3:15])=[O:6]

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 2855718-Crown-6HCID 225921434-bromo-N-[2,4-bis(methylthio)-6-methyl-3-pyridyl]butanamideHCID 1784182821,3-benzoxazole-2-thiol

Product 1

HCID 11774461HCID 11774461, compoundYield 53.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a DMF (2 ml) solution of this amide (105 mg, 0.3 mmol) and 2-mercaptobenzoxazole (50 mg, 0.33 mmol) were added 18-crown-6 (8 mg, 0.03 mmol) and potassium carbonate (50 mg, 0.36 mmol), and the mixture was stirred at 80° C. for 3 hours. 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 preparative thin-layer chromatography (eluent—hexane:ethyl acetate=3:2, eluted twice) to obtain 67 mg (yield 53%) of the desired compound as a colorless needle 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 preparative thin-layer chromatography (eluent—hexane
  6. washethyl acetate=3:2, eluted twice)

Sources & evidence

ORD record
ord-5f47f5358f66452cb5986073572f3d31
Source dataset
uspto-grants-2008_08
Patent number
US07414066B2

Reaction notes

Loading…