HCID 474087, compound → HCID 22130832, compound

HRID 1857768Notes

Reaction equation

HRID 1857768 reaction equation
C([O:8][CH2:9][CH2:10][C:11]1[N:12]([CH2:28][CH2:29][OH:30])[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:27][C:22]1[CH:21]=[C:20]([S:19][C:13]2[N:12]([CH2:28][CH2:29][OH:30])[C:11]([CH2:10][CH2:9][OH:8])=[N:15][C:14]=2[CH:16]([CH3:18])[CH3:17])[CH:25]=[C:24]([Cl:26])[CH:23]=1

Participants

4

Reactant 2

HCID 474087HCID 474087, compoundHCID 516892Sodium Bicarbonate

Product 1

HCID 22130832HCID 22130832, compoundYield 94.9%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Conditions

Temperature
110 °C

Procedure

In 15 ml of cocentrated hydrochloric acid was dissolved 1.5 g (3.2 mmol) of the alcohol compound (130d), and the mixture was heated at 110° C. for 7 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 (3% methanol/ethyl acetate), and 1.14 g of 2-(5-(3,5-dichlorophenylthio)-2-(2-hydroxyethyl)-4-isopropyl-1H-imidazol-1-yl)ethanol (131c) was obtained as oil (yield 94%).

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 (3% methanol/ethyl acetate)

Sources & evidence

ORD record
ord-9e6cec72b5bf44b082cbae98186d6bfa
Source dataset
uspto-grants-2000_11
Patent number
US06147097

Reaction notes

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