Water → 6-Iodo-2-(methylsulfonyl)benzo[d]thiazole

HRID 1691981Notes

Reaction equation

HRID 1691981 reaction equation
[I:1][C:2]1[CH:12]=[CH:11][C:5]2[N:6]=[C:7]([S:9][CH3:10])[S:8][C:4]=2[CH:3]=1.[Mn]([O-])(=O)(=O)=[O:14].[K+].[OH2:19]>C(O)(=O)C>[I:1][C:2]1[CH:12]=[CH:11][C:5]2[N:6]=[C:7]([S:9]([CH3:10])(=[O:14])=[O:19])[S:8][C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 516875Potassium PermanganateHCID 669058856-Iodo-2-(methylthio)benzo[d]thiazole

Product 1

HCID 669061396-Iodo-2-(methylsulfonyl)benzo[d]thiazole

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a stirred, room temperature solution of 6-iodo-2-(methylthio)benzo[d]thiazole (Reference Example 6b, 1.22 g, 4.0 mmol) in acetic acid (100 mL) was added dropwise a solution of potassium permanganate (0.190 g, 1.2 mmol) in water (60 mL). The reaction mixture was stirred at room temperature for 68 hours, then quenched with aqueous sodium sulfite. The resulting mixture was vigorously stirred at room temperature overnight. The resulting precipitate was collected by filtration and rinsed with water. The solid was dissolved in ethyl acetate, dried (MgSO4), and filtered. The filtrate was concentrated under reduced pressure to provide 6-iodo-2-(methylsulfonyl)benzo[d]thiazole. 1H NMR (300 MHz, CDCl3) δ ppm 3.41 (s, 3H), 7.93 (d, J=1 Hz, 2H), 8.38 (t, J=1 Hz, 1H); MS(DCI/NH3) m/z 340 (M+H)−, 357 (M+NH4)+.

Workup

  1. customquenched with aqueous sodium sulfite
  2. stirringThe resulting mixture was vigorously stirred at room temperature overnight
  3. filtrationThe resulting precipitate was collected by filtration
  4. washrinsed with water
  5. dissolutionThe solid was dissolved in ethyl acetate
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-e3d12b99d40443fcb3a317da4461c838
Source dataset
uspto-grants-2012_04
Patent number
US08153813B2

Reaction notes

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