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Potassium Iodide → 1-(2-Dimethylaminoethyl)-2-{[[4-(2-furylmethylthio)-3-methyl-2-pyridinyl]methyl]-thio}-benzimidazole

HRID 1871943
Notes
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Reaction equation

HRID 1871943 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][S:7][C:8]1[CH:13]=[CH:12][N:11]=[C:10]([CH2:14][S:15][C:16]2[NH:20][C:19]3[CH:21]=[CH:22][CH:23]=[CH:24][C:18]=3[N:17]=2)[C:9]=1[CH3:25].Cl.[CH3:27][N:28]([CH3:32])[CH2:29][CH2:30]Cl.C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>C(#N)C>[CH3:27][N:28]([CH3:32])[CH2:29][CH2:30][N:20]1[C:19]2[CH:21]=[CH:22][CH:23]=[CH:24][C:18]=2[N:17]=[C:16]1[S:15][CH2:14][C:10]1[C:9]([CH3:25])=[C:8]([S:7][CH2:6][C:2]2[O:1][CH:5]=[CH:4][CH:3]=2)[CH:13]=[CH:12][N:11]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 97993662-{[[4-(2-Furylmethylthio)-3-methyl-2-pyridinyl]methyl]thio}-1H-benzimidazoleHCID 11636816N,N-Dimethylaminoethyl chloride hydrochloride

Product 1

HCID 186900181-(2-Dimethylaminoethyl)-2-{[[4-(2-furylmethylthio)-3-methyl-2-pyridinyl]methyl]-thio}-benzimidazoleYield 74%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

2-{[[4-(2-Furylmethylthio)-3-methyl-2-pyridinyl]methyl]thio}-1H-benzimidazole is stirred with 2-dimethylamino-ethyl chloride hydrochloride (1.5 equivalents), potassium carbonate (5 equivalents) and potassium iodide (0.05 equivalents) in acetonitrile at 100° C. for 24 h, the mixture is filtered, the filtrate is concentrated on a rotary evaporator, water is added to the residue and the mixture is extracted with methylene chloride. The combined organic phases are washed with water, dried and concentrated. The residue is crystallized from methylene chloride/diisopropyl ether. The title compound is obtained as a colorless powder; m.p. 87-89° C.; yield: 74% of theory.

Workup

  1. filtrationthe mixture is filtered
  2. concentrationthe filtrate is concentrated on a rotary evaporator, water
  3. additionis added to the residue
  4. extractionthe mixture is extracted with methylene chloride
  5. washThe combined organic phases are washed with water
  6. customdried
  7. concentrationconcentrated
  8. customThe residue is crystallized from methylene chloride/diisopropyl ether

Sources & evidence

ORD record
ord-c13319dfaea3499f96d5798384213b91
Source dataset
uspto-grants-2000_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06107312

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes