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1H-Imidazole, 5-((3,5-dichlorophenyl)thio)-1-ethyl-4-(1-methylethyl)-2-(2-(phenylmethoxy)ethyl)- → 1H-Imidazole-2-ethanol, 5-((3,5-dichlorophenyl)thio)-1-ethyl-4-(1-methylethyl)-

HRID 1857756
Notes
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Reaction equation

HRID 1857756 reaction equation
C([O:8][CH2:9][CH2:10][C:11]1[N:12]([CH2:28][CH3:29])[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][CH3:29])[C:11]([CH2:10][CH2:9][OH:8])=[N:15][C:14]=2[CH:16]([CH3:17])[CH3:18])[CH:21]=[C:22]([Cl:27])[CH:23]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 4740951H-Imidazole, 5-((3,5-dichlorophenyl)thio)-1-ethyl-4-(1-methylethyl)-2-(2-(phenylmethoxy)ethyl)-HCID 516892Sodium Bicarbonate

Product 1

HCID 4740961H-Imidazole-2-ethanol, 5-((3,5-dichlorophenyl)thio)-1-ethyl-4-(1-methylethyl)-Yield 85%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Conditions

Temperature
100 °C

Procedure

In 16 ml of cocentrated hydrochloric acid was dissolved 3.8 g (8.5 mmol) of the benzyl compound (122a), and the mixture was heated at 100° C. for 2 hours. After cooling, the mixture was neutralized with sodium hydrogen carbonate, 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 (1% methanol:ethyl acetate), washed with n-hexane, and filtered to give 2.57 g of 2-[5-(3,5-dichlorophenylthio)-1-ethyl-4-isopropyl-1H-imidazol-2-yl]ethanol (123a) as crystals (yield 85%). mp 80-81° C.

Workup

  1. temperatureAfter cooling
  2. extractionextracted with ethyl acetate
  3. washthe extract was washed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (1% methanol:ethyl acetate)
  8. washwashed with n-hexane
  9. filtrationfiltered

Sources & evidence

ORD record
ord-9cdd68e11446406b8abf7246844413a2
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