HCID 474081, compound → HCID 474087, compound

HRID 1857767Notes

Reaction equation

HRID 1857767 reaction equation
C([O:4][CH2:5][CH2:6][N:7]1[C:11]([S:12][C:13]2[CH:18]=[C:17]([Cl:19])[CH:16]=[C:15]([Cl:20])[CH:14]=2)=[C:10]([CH:21]([CH3:23])[CH3:22])[N:9]=[C:8]1[CH2:24][CH2:25][O:26][CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)(=O)C.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C(OCC)C.O>[CH2:27]([O:26][CH2:25][CH2:24][C:8]1[N:7]([CH2:6][CH2:5][OH:4])[C:11]([S:12][C:13]2[CH:18]=[C:17]([Cl:19])[CH:16]=[C:15]([Cl:20])[CH:14]=2)=[C:10]([CH:21]([CH3:23])[CH3:22])[N:9]=1)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Participants

5

Reactant 2

HCID 474081HCID 474081, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 474087HCID 474087, compoundYield 91%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

In 30 ml of dry diethyl ether was dissolved 3.0 g (5.9 mmol) of the ester compound (130c), followed by addition of 230 mg (6 mmol) of lithium aluminum hydride under ice-cooling, and the mixture was stirred at room temperature for 15 minutes. The mixture was diluted with water, 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 (ethyl acetate), and further recrystallized from ethyl acetate-n-hexane to give 2.5 g of 2-(2-(2-benzyloxyethyl)-5-(3,5-dichlorophenylthio)-4-isopropyl-1H-imidazol-1-yl)ethanol (130d) as crystals (yield 91%). mp 129-130° C.

Workup

  1. temperaturecooling
  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 (ethyl acetate)
  8. customfurther recrystallized from ethyl acetate-n-hexane

Sources & evidence

ORD record
ord-24b3825846e145ec9e49e117df53d2b2
Source dataset
uspto-grants-2000_11
Patent number
US06147097

Reaction notes

Loading…