Acetic Acid → HCID 54460378, compound

HRID 1416015Notes

Reaction equation

HRID 1416015 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([S:9][C:10]2[N:14]([CH3:15])[C:13]([CH2:16][O:17][CH2:18][CH:19]=[O:20])=[N:12][C:11]=2[CH:21]([CH3:23])[CH3:22])[CH:5]=[C:6]([Cl:8])[CH:7]=1.[BH4-].[Na+].C(O)(=O)C.C(=O)([O-])O.[Na+]>C(O)C>[Cl:1][C:2]1[CH:3]=[C:4]([S:9][C:10]2[N:14]([CH3:15])[C:13]([CH2:16][O:17][CH2:18][CH2:19][OH:20])=[N:12][C:11]=2[CH:21]([CH3:23])[CH3:22])[CH:5]=[C:6]([Cl:8])[CH:7]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 516892Sodium BicarbonateHCID 4311764Sodium borohydrideHCID 54509160HCID 54509160, compound

Product 1

HCID 54460378HCID 54460378, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In ethanol (6 ml)was dissolved 220 mg (0.59 mmol)of [5-(3,5-dichlorophenylthio)-4-isopropyl-1-methyl-1H-imidazol-2-ylmethoxy]acetaldehyde (24a), followed by addition of 45 mg (1.2 mmol)of sodium borohydride, and the mixture was stirred for 15 minutes. The reaction mixture was weakly acidified with acetic acid. A saturated aqueous sodium hydrogen carbonate solution was added to neutralize again, and the mixture was extracted with methylene chloride. The extract was washed with water and dried over sodium sulfate. The solvent was distilled off under reduced pressure, and the residue was fractionated by silica gel chromatography (ethyl acetate). The product was recrystallized from n-hexane to give 144 mg of 2-{[5-(3,5-dichlorophenylthio)-4-isopropyl-1-methyl-1H-imidazol-2-yl]methoxy}ethanol (25a)(yield 65%). mp 89-90° C.

Workup

  1. extractionthe mixture was extracted with methylene chloride
  2. washThe extract was washed with water
  3. dry with materialdried over sodium sulfate
  4. distillationThe solvent was distilled off under reduced pressure
  5. customThe product was recrystallized from n-hexane

Sources & evidence

ORD record
ord-42f7d087261f4074a245a22c347c8983
Source dataset
uspto-grants-1999_06
Patent number
US05910506

Reaction notes

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