Sodium Hydroxide → 2,4-Diiodo-6-sulfanylphenol

HRID 371676Notes

Reaction equation

HRID 371676 reaction equation
[I-].[I:2][C:3]1[CH:4]=[C:5]([I:15])[C:6]2[O:10]C(=[N+](C)C)[S:8][C:7]=2[CH:14]=1.[OH-].[Na+]>CO>[I:15][C:5]1[CH:4]=[C:3]([I:2])[CH:14]=[C:7]([SH:8])[C:6]=1[OH:10]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 20355597HCID 20355597, compound

Product 1

HCID 203555942,4-Diiodo-6-sulfanylphenolYield 69.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

An amount of 13 g (23.3 m mol) of N-(5,7-diiodo-1,3-benzoxathiol-2-ylidene)-N-methylmethanaminium iodide was heated at reflux for 4 hours in a mixture of 200 ml of methanol and 50 ml of aqueous 10 percent sodium hydroxide. The reaction mixture was filtered, added to 400 ml of water and acidified with hydrochloric acid. The mixture was extracted with methylene chloride. After drying over anhydrous sodium sulfate, the methylene chloride extract was condensed in vacuo to give 6.1 g (69.4 percent yield) of 2,4-diiodo-6-mercaptophenol: M.P. 177.5°-179.5° C; nmr (DMSO-d6) δ 7.96 (doublet), 7.57 (doublet), and 3.42 (broad singlet).

Workup

  1. filtrationThe reaction mixture was filtered
  2. additionadded to 400 ml of water
  3. extractionThe mixture was extracted with methylene chloride
  4. dry with materialAfter drying over anhydrous sodium sulfate
  5. extractionthe methylene chloride extract
  6. customcondensed in vacuo

Sources & evidence

ORD record
ord-3c26fa667aa840dba4bb46d5f6b0d7c2
Source dataset
uspto-grants-1978_05
Patent number
US04087445

Reaction notes

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