Potassium Carbonate → HCID 11260067, compound

HRID 746645Notes

Reaction equation

HRID 746645 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7]([NH:9][C:10]1[C:11]([S:20][CH2:21][CH3:22])=[N:12][C:13]([CH3:19])=[CH:14][C:15]=1[S:16][CH2:17][CH3:18])=[O:8].[SH:23][C:24]1[O:25][C:26]2[CH:32]=[CH:31][CH:30]=[CH:29][C:27]=2[N:28]=1.C(=O)([O-])[O-].[K+].[K+].C1OCCOCCOCCOCCOCCOC1>CN(C=O)C>[O:25]1[C:26]2[CH:32]=[CH:31][CH:30]=[CH:29][C:27]=2[N:28]=[C:24]1[S:23][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7]([NH:9][C:10]1[C:11]([S:20][CH2:21][CH3:22])=[N:12][C:13]([CH3:19])=[CH:14][C:15]=1[S:16][CH2:17][CH3:18])=[O:8]

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 2855718-Crown-6HCID 22592163HCID 22592163, compoundHCID 1784182821,3-benzoxazole-2-thiol

Product 1

HCID 11260067HCID 11260067, compoundYield 46%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

The reaction and the treatment were conducted in the same manner as in Example 26 except that 6-bromohexanoyl chloride was used instead of bromoacetyl bromide to obtain 6-bromo-N-[2,4-bis(ethylthio)-6-methyl-3-pyridyl]hexanamide. To a DMF (2 ml) solution of this amide (122 mg, 0.3 mmol) and 2-mercaptobenzoxazole (45 mg, 0.3 mmol) were added potassium carbonate (46 mg, 0.33 mmol) and 18-crown-6 (8 mg, 0.03 mmol), and the mixture was stirred at 80° C. for 1.5 hours. The reaction mixture was allowed to cool, 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 residue was purified through preparative thin-layer chromatography (eluent—hexane:acetone=5:2) to obtain 65 mg (yield 46%) of the desired compound as a light brown needle crystal.

Workup

  1. temperatureto cool
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with water
  4. dry with materialwith a saturated aqueous solution of sodium chloride, and dried over sodium sulfate
  5. distillationSubsequently, the solvent was distilled off
  6. customthe resulting residue was purified through preparative thin-layer chromatography (eluent—hexane:acetone=5:2)

Sources & evidence

ORD record
ord-9406dc7b60784bddafd21223aa00546d
Source dataset
uspto-grants-2008_07
Patent number
US07393866B2

Reaction notes

Loading…