Chloroform → HCID 14207290, compound

HRID 1647741Notes

Reaction equation

HRID 1647741 reaction equation
[C:1]1([N:7]2[CH:11]=[CH:10][N:9]=[C:8]2[S:12]([CH2:14][C:15]([C:17]2[CH:18]=[C:19]3[C:24](=[CH:25][CH:26]=2)[NH:23][C:22](=[O:27])[CH2:21][CH2:20]3)=[O:16])=[O:13])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Mn]([O-])(=O)(=O)=[O:29].[K+].C(Cl)(Cl)Cl>C(O)(=O)C.O>[C:1]1([N:7]2[CH:11]=[CH:10][N:9]=[C:8]2[S:12]([CH2:14][C:15]([C:17]2[CH:18]=[C:19]3[C:24](=[CH:25][CH:26]=2)[NH:23][C:22](=[O:27])[CH2:21][CH2:20]3)=[O:16])(=[O:29])=[O:13])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 3

HCID 6212ChloroformHCID 516875Potassium PermanganateHCID 14207289HCID 14207289, compound

Product 1

HCID 14207290HCID 14207290, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

3.79 Grams (10 mM) of 6-[2-(1-phenyl-2-imidazolyl)sulfinylacetyl]-3,4-dihydrocarbostyril was dissolved in a mixture of 240 ml of acetic acid with 100 ml of water, then 5.06 g (32 mM) of potassium permanganate was added thereto. This mixture was stirred at room temperature for 2 days. After the reaction was completed, chloroform was added to the reaction mixture and filtered with Celite (a trademark for distomaceous earth product, manufactured by Johns-Manville Proudcts Corp.). The filtrate was washed with water and dried with anhydrous magnensium sulfate. The residue obtained by removing the solvent was purified by means of a silica gel column chromatography (eluent: chloroform:methanol=30:1), and recrystallized from ethanol-chloroform to yield 0.6 g of 6-[2-(1-phenyl-2-imidazolyl)sulfonylacetyl]-3,4-dihydrocarbostyril. Light yellow granular substance. Melting point: 199°-201° C.

Workup

  1. filtrationfiltered with Celite (a trademark for distomaceous earth product
  2. washThe filtrate was washed with water
  3. dry with materialdried with anhydrous magnensium sulfate
  4. customThe residue obtained
  5. customby removing the solvent
  6. customwas purified by means of a silica gel column chromatography (eluent: chloroform:methanol=30:1)
  7. customrecrystallized from ethanol-chloroform

Sources & evidence

ORD record
ord-889805e23317490f95dbda1d2119d7cc
Source dataset
uspto-grants-1995_07
Patent number
US05434164

Reaction notes

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