HCID 13026939, compound → HCID 12928447, compound

HRID 2052457Notes

Reaction equation

HRID 2052457 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[S:11][CH2:10][CH2:9][CH:8]=[C:7]([OH:12])[C:6]=2[CH:13]=1.I([O-])(=O)(=O)=[O:15].[Na+]>CO.O1CCOCC1.O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[S:11](=[O:15])[CH2:10][CH2:9][CH:8]=[C:7]([OH:12])[C:6]=2[CH:13]=1

Participants

6

Reactant 2

HCID 13026939HCID 13026939, compoundHCID 23667635Sodium periodate

Product 1

HCID 12928447HCID 12928447, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

The starting material is prepared as follows: The solution of 6.4 g of 7-chloro-5-hydroxy-2,3-dihydro-1-benzothiepin in 65 ml of dry methanol and 65 ml of dry dioxane is treated dropwise at 0° in 1 hour with the solution of 7.0 g of sodium metaperiodate in 65 ml water. The mixture is stirred at 0° for two hours after the addition period and then allowed to warm to room temperature for overnight. It is filtered and the solid rinsed with 30 ml of methanol. The combined filtrate and wash is concentrated to a smaller volume and treated with 40 ml of water. The mixture is extracted with chloroform, the extract separated, washed with water, dried and evaporated, to yield the 7-chloro-5-hydroxy-2,3-dihydro-1-benzothiepin-1-oxide boiling at 154°-157/0.25 mmHg.

Workup

  1. customThe starting material is prepared
  2. additionafter the addition period
  3. filtrationIt is filtered
  4. washthe solid rinsed with 30 ml of methanol
  5. washThe combined filtrate and wash
  6. concentrationis concentrated to a smaller volume
  7. additiontreated with 40 ml of water
  8. extractionThe mixture is extracted with chloroform
  9. customthe extract separated
  10. washwashed with water
  11. customdried
  12. customevaporated

Sources & evidence

ORD record
ord-df709bfc25b74ee9a8ff8d38f9765e71
Source dataset
uspto-grants-1980_01
Patent number
US04185109

Reaction notes

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