Hydrochloric Acid → K-604

HRID 2103968Notes

Reaction equation

HRID 2103968 reaction equation
C(=O)([O-])[O-].[K+].[K+].[N:7]1[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[NH:9][C:8]=1[S:16][CH2:17][CH2:18][N:19]1[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]1.Cl.Br[CH2:27][C:28]([NH:30][C:31]1[C:32]([S:40][CH3:41])=[N:33][C:34]([CH3:39])=[CH:35][C:36]=1[S:37][CH3:38])=[O:29]>O.C(#N)C>[N:7]1[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[NH:9][C:8]=1[S:16][CH2:17][CH2:18][N:19]1[CH2:24][CH2:23][N:22]([CH2:27][C:28]([NH:30][C:31]2[C:32]([S:40][CH3:41])=[N:33][C:34]([CH3:39])=[CH:35][C:36]=2[S:37][CH3:38])=[O:29])[CH2:21][CH2:20]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 99617871-[2-(Benzimidazol-2-ylthio)ethyl]piperazineHCID 222471492-Bromo-N-(6-methyl-2,4-bis(methylthio)pyridin-3-yl)acetamide

Product 1

HCID 9892288K-604Yield 99%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6342AcetonitrileSolvent

Procedure

Acetonitrile (450 mL) and potassium carbonate (85.7 g, 0.62 mol) were added to 1-[2-(benzimidazol-2-ylthio)ethyl]piperazine.3 hydrochloride (59.42 g, 0.16 mol) in water (180 mL). Subsequently, 2-bromo-N-[2,4-bis(methylthio)-6-methylpyridin-3-yl]acetamide (48.19 g, 0.15 mol) was gradually added thereto, and the resultant mixture was stirred at room temperature for 2 hours. The reaction mixture was diluted with water (300 mL), followed by stirring for 1 hour. The crystals that precipitated were separated through filtration, followed by washing with a solvent mixture (600 mL) of acetonitrile and water (1:1), washing with water (200 mL), and drying through air blow at 40 to 50° C., to thereby yield 2-[4-[2-(benzimidazol-2-ylthio)ethyl]piperazin-1-yl]-N-[2,4-bis(methylthio)-6-methylpyridin-3-yl]acetamide as colorless crystals (75 g, yield: 99%).

Workup

  1. customThe crystals that precipitated
  2. customwere separated through filtration
  3. washby washing with a solvent mixture (600 mL) of acetonitrile and water (1:1)
  4. washwashing with water (200 mL)
  5. customdrying through air blow at 40 to 50° C.

Sources & evidence

ORD record
ord-52fba4a3f87e4cb68c3ddc8ec7822d86
Source dataset
uspto-grants-2009_08
Patent number
US07576203B2

Reaction notes

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