Water → HCID 67547429, compound

HRID 2356715Notes

Reaction equation

HRID 2356715 reaction equation
Cl.Cl.[F:3][C:4]1[CH:5]=[C:6]([C:10]2[NH:11][C:12]([CH2:21]Cl)=[C:13]([C:15]3[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=3)[N:14]=2)[CH:7]=[CH:8][CH:9]=1.[CH3:23][S:24]C.[Na].C(N(CC)CC)C.O>O1CCCC1>[F:3][C:4]1[CH:5]=[C:6]([C:10]2[NH:11][C:12]([CH2:21][S:24][CH3:23])=[C:13]([C:15]3[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=3)[N:14]=2)[CH:7]=[CH:8][CH:9]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 67546965HCID 67546965, compoundHCID 86593196Sodium methylsulfide

Product 1

HCID 67547429HCID 67547429, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of a crude product of 2-(3-fluorophenyl)-5-chloromethyl-4-(3-pyridyl)imidazole dihydrochloride (268 mg) in tetrahydrofuran (10 ml) were added 15% aqueous sodium methyl sulfide solution (0.95 ml) and triethylamine (206 mg), and the mixture was stirred at room temperature for 1.5 hours. Water was added to the reaction mixture, and the reaction mixture was extracted with ethyl acetate. The organic layer was washed with brine and dried over anhydrous sodium sulfate, and the solvent was removed under reduced pressure. The resulting residue was purified by silica gel column chromatography (solvent: chloroform:methanol=19:1) to obtain 2-(3-fluorophenyl)-5-methylthiomethyl-4-(3-pyridyl)imidazole (198 mg) as colorless powder.

Workup

  1. extractionthe reaction mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customthe solvent was removed under reduced pressure
  5. customThe resulting residue was purified by silica gel column chromatography (solvent: chloroform:methanol=19:1)

Sources & evidence

ORD record
ord-f9b05ac0583d47d3810a3fb2e20b75eb
Source dataset
uspto-grants-2010_07
Patent number
US07759373B2

Reaction notes

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