Sodium periodate → HCID 178510499, compound

HRID 485264Notes

Reaction equation

HRID 485264 reaction equation
I([O-])(=O)(=O)=[O:2].[Na+].[NH2:7]/[C:8](/[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[C:9]1\[C:10](=[O:18])[C:11]2[CH:17]=[CH:16][CH:15]=[CH:14][C:12]=2[S:13]\1>O.CO>[NH2:7]/[C:8](/[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[C:9]1\[C:10](=[O:18])[C:11]2[CH:17]=[CH:16][CH:15]=[CH:14][C:12]=2[S:13]\1=[O:2]

Participants

5

Reactant 2

HCID 23667635Sodium periodateHCID 178510717HCID 178510717, compound

Product 1

HCID 178510499HCID 178510499, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A solution of 2.246 gm (0.0105 mol) of sodium metaperiodate in 10 ml of water was added to a solution of 2.53 gm (0.01 mol) of (E)-2-[(amino)phenylmethylene]-benzo[b]-thiophen-3(2H)-one in 150 ml of methanol, and the mixture was stirred at room temperature for 15 hours. The sodium iodate precipitated thereby was removed by filtration, and the filtrate was diluted with 300 ml of water and extracted exhaustively with dichloromethane. The combined extracts were washed once with water, dried over sodium sulfate and concentrated by evaporation in vacuo. The residue was recrystallized from ethanol/ethyl acetate using activated charcoal, and yielded 2.28 gm (85% of theory) of pale yellow crystals, m.p. 246°-247° C. (decomposition).

Workup

  1. customThe sodium iodate precipitated
  2. customthereby was removed by filtration
  3. additionthe filtrate was diluted with 300 ml of water
  4. extractionextracted exhaustively with dichloromethane
  5. washThe combined extracts were washed once with water
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated by evaporation in vacuo
  8. customThe residue was recrystallized from ethanol/ethyl acetate using activated charcoal
  9. customyielded 2.28 gm (85% of theory) of pale yellow crystals, m.p. 246°-247° C. (decomposition)

Sources & evidence

ORD record
ord-b9ff2f39b64f4f93928f31c9b12057e1
Source dataset
uspto-grants-1985_08
Patent number
US04536402

Reaction notes

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