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Ethanol → 2-[[(4 Ethoxy-3-methyl-2-pyridyl) methyl]thio]-5-(trifluoromethyl)benzimidazole

HRID 1709770
Notes
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Reaction equation

HRID 1709770 reaction equation
[H-].[Na+].[CH2:3]([OH:5])[CH3:4].[CH3:6][C:7]1[C:8]([CH2:16][S:17][C:18]2[NH:19][C:20]3[CH:26]=[C:25]([C:27]([F:30])([F:29])[F:28])[CH:24]=[CH:23][C:21]=3[N:22]=2)=[N:9][CH:10]=[CH:11][C:12]=1[N+]([O-])=O>C(O)(=O)C>[CH2:3]([O:5][C:12]1[CH:11]=[CH:10][N:9]=[C:8]([CH2:16][S:17][C:18]2[NH:19][C:20]3[CH:26]=[C:25]([C:27]([F:28])([F:29])[F:30])[CH:24]=[CH:23][C:21]=3[N:22]=2)[C:7]=1[CH3:6])[CH3:4]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 702EthanolHCID 24758Sodium hydrideHCID 230364992-[[(3-Methyl-4-nitro 2-pyridyl)methyl]thio]-5-(trifluoromethyl)benzimidazole

Product 1

HCID 230365182-[[(4 Ethoxy-3-methyl-2-pyridyl) methyl]thio]-5-(trifluoromethyl)benzimidazole

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

600 mg of sodium hydride dispersion (55-60% in oil) were dissolved in 50 ml of abs. ethanol under argon. 3.68 g of 2-[[(3-methyl-4-nitro-2-pyridyl)methyl]thio]-5-(trifluoromethyl)benzimidazole were added thereto and the solution was left to stir at 70° for 1 hour. The solution was neutralized with glacial acetic acid and the mixture was then evaporated in a vacuum. The residue was treated with aqueous sodium bicarbonate solution and methylene chloride. The organic phase was separated and the aqueous phase was extracted several times with methylene chloride. The combined organic phases were dried and concentrated The residue was chromatographed on silica gel with methylene chloride/methanol (9:1), using the medium pressure flash chromatography method, pressure was produced with nitrogen gas. There was obtained 2-[[(4-ethoxy-3-methyl-2-pyridyl)methyl]thio]-5-(trifluoromethyl)benzimidazole. After recrystallization from ethyl acetate/ether the product melts at 173°-177°.

Workup

  1. waitthe solution was left
  2. customthe mixture was then evaporated in a vacuum
  3. additionThe residue was treated with aqueous sodium bicarbonate solution and methylene chloride
  4. customThe organic phase was separated
  5. extractionthe aqueous phase was extracted several times with methylene chloride
  6. customThe combined organic phases were dried
  7. concentrationconcentrated The residue
  8. customwas chromatographed on silica gel with methylene chloride/methanol (9:1)
  9. custompressure was produced with nitrogen gas

Sources & evidence

ORD record
ord-7f527923ff744e468db985998b32219b
Source dataset
uspto-grants-1990_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04950677

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes