Potassium Carbonate → HCID 22592168, compound

HRID 746647Notes

Reaction equation

HRID 746647 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7]([NH:9][C:10]1[C:11]([S:21][CH:22]([CH3:24])[CH3:23])=[N:12][C:13]([CH3:20])=[CH:14][C:15]=1[S:16][CH:17]([CH3:19])[CH3:18])=[O:8].[SH:25][C:26]1[O:27][C:28]2[CH:34]=[CH:33][CH:32]=[CH:31][C:29]=2[N:30]=1.C(=O)([O-])[O-].[K+].[K+].C1OCCOCCOCCOCCOCCOC1>CN(C=O)C>[O:27]1[C:28]2[CH:34]=[CH:33][CH:32]=[CH:31][C:29]=2[N:30]=[C:26]1[S:25][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7]([NH:9][C:10]1[C:11]([S:21][CH:22]([CH3:24])[CH3:23])=[N:12][C:13]([CH3:20])=[CH:14][C:15]=1[S:16][CH:17]([CH3:19])[CH3:18])=[O:8]

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 2855718-Crown-6HCID 22592175HCID 22592175, compoundHCID 1784182821,3-benzoxazole-2-thiol

Product 1

HCID 22592168HCID 22592168, compoundYield 79.4%

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 35 except that 6-bromohexanoyl chloride was used instead of bromoacetyl bromide to obtain 6-bromo-N-[2,4-bis(isopropylthio)-6-methyl-3-pyridyl]hexanamide. To a DMF (4 ml) solution of this amide (100 mg, 0.23 mmol) and 2-mercaptobenzoxazole (35 mg, 0.23 mmol) were added potassium carbonate (38 mg, 0.28 mmol) and 18-crown-6 (6 mg, 0.02 mmol), and the mixture was stirred at 80° C. for 2.5 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:ethyl acetate=3:1) to obtain 92 mg (yield 79%) of the desired compound as a colorless powdery 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:ethyl acetate=3:1)

Sources & evidence

ORD record
ord-f2545c10e5674577a91b8e948e853766
Source dataset
uspto-grants-2008_07
Patent number
US07393866B2

Reaction notes

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