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Hydrogen Peroxide → HCID 23028618, compound

HRID 748865
Notes
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Reaction equation

HRID 748865 reaction equation
OO.Cl[C:4]1C(C(SC2C=NC(Cl)=CC=2)C2C=CN=CC=2)=NC(Cl)=CC=1.C(OCC)(=O)C.[Si:32]([O:39][CH2:40][CH2:41][CH:42](C)[CH:43]([C:54]1[CH:59]=[C:58]([F:60])[CH:57]=[CH:56][C:55]=1[F:61])[S:44]([C:47]1[CH:52]=[CH:51][C:50]([Cl:53])=[CH:49][CH:48]=1)(=[O:46])=[O:45])([C:35]([CH3:38])([CH3:37])[CH3:36])([CH3:34])[CH3:33]>CO.CCCCCC>[Si:32]([O:39][CH:40]([CH3:4])[CH2:41][CH2:42][CH:43]([C:54]1[CH:59]=[C:58]([F:60])[CH:57]=[CH:56][C:55]=1[F:61])[S:44]([C:47]1[CH:48]=[CH:49][C:50]([Cl:53])=[CH:51][CH:52]=1)(=[O:46])=[O:45])([C:35]([CH3:36])([CH3:38])[CH3:37])([CH3:33])[CH3:34]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 784Hydrogen PeroxideHCID 8857Ethyl Acetate2×HCID 231147773,6-Dichloro-2-[(6-chloropyridin-3-ylthio)(pyridin-4-yl)methyl]pyridineHCID 59750761HCID 59750761, compound

Product 1

HCID 23028618HCID 23028618, compoundYield 20.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent
HCID 8058HexaneSolvent

Procedure

A 31% aqueous hydrogen peroxide solution (2 ml) and hexaammonium heptamolybdate tetrahydrate (30 mg) were added to a solution of 3,6-dichloro-2-[(6-chloropyridin-3-ylthio) (pyridin-4-yl)methyl]pyridine (82 mg, 0.24 mmol) in methanol (4 ml). The resulting mixture was stirred at room temperature for 2 hours. Ethyl acetate was added to the reaction mixture. After washing with a saturated aqueous solution of sodium bicarbonate, the organic layer was dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated under reduced pressure. The residue was subjected to flash chromatography on a silica gel column. A fraction obtained from the elution portion with hexane:ethyl acetate=3:2 was concentrated under reduced pressure, whereby the title compound A (41 mg, 0.098 mmol, 46%) was obtained. A fraction obtained from the elution portion with hexane:ethyl acetate=1:1 was concentrated under reduced pressure, whereby the title compound B (isomer A) (low polarity) (8 mg, 0.020 mmol, 9%) and the title compound B (isomer B) (high polarity) (8 mg, 0.020 mmol, 9%) were obtained, respectively each as a white solid.

Workup

  1. washAfter washing with a saturated aqueous solution of sodium bicarbonate
  2. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. customA fraction obtained from the elution portion with hexane
  6. customwas obtained
  7. concentrationethyl acetate=1:1 was concentrated under reduced pressure, whereby the title compound B (isomer A) (low polarity) (8 mg, 0.020 mmol, 9%)

Sources & evidence

ORD record
ord-273f7493e00542ffb7aa237e61b41234
Source dataset
uspto-grants-2008_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07399775B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes