Iodine → 6-Hydroxy-7-iodo-benzothiazole

HRID 228859Notes

Reaction equation

HRID 228859 reaction equation
[OH:1][C:2]1[CH:10]=[CH:9][C:5]2[N:6]=[CH:7][S:8][C:4]=2[CH:3]=1.[I:11]I.S([O-])([O-])=O.[Na+].[Na+]>CO.O>[OH:1][C:2]1[CH:10]=[CH:9][C:5]2[N:6]=[CH:7][S:8][C:4]=2[C:3]=1[I:11]

Participants

5

Reactant 3

HCID 807IodineHCID 24437Sodium SulfiteHCID 1518116-Hydroxybenzothiazole

Product 1

HCID 230784406-Hydroxy-7-iodo-benzothiazoleYield 29.5%

Reagents, catalysts & solvents 1

HCID 22242641Methanol--water (1/1)Solvent

Procedure

6-Hydroxy-benzothiazole (0.39 g) and iodine (1.32 g) were dissolved in methanol/water (15 ml/5 ml) to prepare a solution which was then stirred at room temperature for 2 days. An aqueous sodium sulfite solution was added to the reaction solution, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was then washed with water and was dried over anhydrous sodium sulfate. The solvent was removed by distillation under the reduced pressure, and the residue was purified by column chromatography using acetone-chloroform to give 6-hydroxy-7-iodo-benzothiazole (211 mg, yield 29%).

Workup

  1. customto prepare a solution which
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe ethyl acetate layer was then washed with water
  4. dry with materialwas dried over anhydrous sodium sulfate
  5. customThe solvent was removed by distillation under the reduced pressure
  6. customthe residue was purified by column chromatography

Sources & evidence

ORD record
ord-e4ffdf2d0c8043cda58873b24e61dd2a
Source dataset
uspto-grants-2009_07
Patent number
US07560558B2

Reaction notes

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