Potassium Carbonate → K-604

HRID 890829Notes

Reaction equation

HRID 890829 reaction equation
Cl.Cl.Cl.[N:4]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[NH:6][C:5]=1[S:13][CH2:14][CH2:15][N:16]1[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]1.C(=O)([O-])[O-].[K+].[K+].[CH3:28][S:29][C:30]1[C:35]([NH:36][C:37](=[O:40])[CH2:38]Br)=[C:34]([S:41][CH3:42])[CH:33]=[C:32]([CH3:43])[N:31]=1>C(#N)C.O>[N:4]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[NH:6][C:5]=1[S:13][CH2:14][CH2:15][N:16]1[CH2:21][CH2:20][N:19]([CH2:38][C:37]([NH:36][C:35]2[C:30]([S:29][CH3:28])=[N:31][C:32]([CH3:43])=[CH:33][C:34]=2[S:41][CH3:42])=[O:40])[CH2:18][CH2:17]1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 10384617HCID 10384617, compoundHCID 222471492-Bromo-N-(6-methyl-2,4-bis(methylthio)pyridin-3-yl)acetamide

Product 1

HCID 9892288K-604Yield 91.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6342AcetonitrileSolvent

Procedure

1-[2-(Benzimidazol-2-ylthio)ethyl]piperazine trihydrochloride 1.0 g (2.69 mmol) was suspended in acetonitrile (30 mL), and potassium carbonate 1.45 g (10.49 mmol) was added to the suspension. Water (8 mL) was added dropwise to the mixture under stirring at room temperature until the entirety of the suspension assumed a homogeneous solution. Subsequently, N-[2,4-bis(methylthio)-6-methylpyridin-3-yl]-2-bromoacetamide 810 mg (2.52 mmol) was gradually added to the mixture, and the mixture was stirred for 2.5 hours at room temperature. The reaction mixture was diluted with water (50 mL) and extracted with chloroform (100 mL×3). The organic layer was washed with saturated brine (50 mL), followed by drying over sodium sulfate anhydrate and concentrating under reduced pressure. The residue was purified through silica gel column chromatography (eluent: chloroform:saturated ammonia in methanol=20:1). The thus-obtained oily product was crystallized from ethanol-diethyl ether, thereby yielding 1.16 g of 2-[4-[2-(benzimidazol-2-ylthio)ethyl]piperazin-1-yl]-N-[2,4-bis(methylthio)-6-methylpyridin-3-yl]acetamide (yield: 88%) as a colorless crystalline powder.

Workup

  1. stirringthe mixture was stirred for 2.5 hours at room temperature
  2. extractionextracted with chloroform (100 mL×3)
  3. washThe organic layer was washed with saturated brine (50 mL)
  4. dry with materialby drying over sodium sulfate anhydrate
  5. concentrationconcentrating under reduced pressure
  6. customThe residue was purified through silica gel column chromatography (eluent: chloroform:saturated ammonia in methanol=20:1)
  7. customThe thus-obtained oily product was crystallized from ethanol-diethyl ether

Sources & evidence

ORD record
ord-58e4656eb8a74f49a9ebbc61794f2920
Source dataset
uspto-grants-2006_02
Patent number
US06998486B2

Reaction notes

Loading…