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Pyridine, 4-((5-((3,5-dichlorophenyl)thio)-4-(1-methylethyl)-2-(2-(phenylmethoxy)ethyl)-1H-imidazol-1-yl)methyl)- → 1H-Imidazole-2-ethanol, 5-((3,5-dichlorophenyl)thio)-4-(1-methylethyl)-1-(4-pyridinylmethyl)-

HRID 1857758
Notes
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Reaction equation

HRID 1857758 reaction equation
C([O:8][CH2:9][CH2:10][C:11]1[N:12]([CH2:28][C:29]2[CH:34]=[CH:33][N:32]=[CH:31][CH:30]=2)[C:13]([S:19][C:20]2[CH:25]=[C:24]([Cl:26])[CH:23]=[C:22]([Cl:27])[CH:21]=2)=[C:14]([CH:16]([CH3:18])[CH3:17])[N:15]=1)C1C=CC=CC=1.C(=O)([O-])O.[Na+]>Cl>[Cl:26][C:24]1[CH:25]=[C:20]([S:19][C:13]2[N:12]([CH2:28][C:29]3[CH:34]=[CH:33][N:32]=[CH:31][CH:30]=3)[C:11]([CH2:10][CH2:9][OH:8])=[N:15][C:14]=2[CH:16]([CH3:18])[CH3:17])[CH:21]=[C:22]([Cl:27])[CH:23]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 474064Pyridine, 4-((5-((3,5-dichlorophenyl)thio)-4-(1-methylethyl)-2-(2-(phenylmethoxy)ethyl)-1H-imidazol-1-yl)methyl)-HCID 516892Sodium Bicarbonate

Product 1

HCID 4740651H-Imidazole-2-ethanol, 5-((3,5-dichlorophenyl)thio)-4-(1-methylethyl)-1-(4-pyridinylmethyl)-Yield 67.3%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Conditions

Temperature
100 °C

Procedure

In 12 ml of cocentrated hydrochloric acid was dissolved 2.3 g (4.5 mmol) of the benzyl compound (122b), and the mixture was heated at 100° C. for 4 hours. The mixture was neutralized with sodium hydrogen carbonate, and extracted with ethyl acetate. The extract was washed with water, dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (7% methanol/ethyl acetate) to give 1.28 g of 2-[5-(3,5-dichlorophenylthio)-4-isopropyl-1-(pyridin-4-ylmethyl)-1H-imidazol-2-yl]ethanol (123b) as crystals (yield 67%). mp 121-122° C.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with water
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (7% methanol/ethyl acetate)

Sources & evidence

ORD record
ord-930a7d0a015847d195096d852802c1b3
Source dataset
uspto-grants-2000_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06147097

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes