m-Chloroperbenzoic acid → 6-((4-bromo-1H-imidazol-1-yl)methyl)-2-(methylsulfinyl)benzo[d]thiazole

HRID 1847994Notes

Reaction equation

HRID 1847994 reaction equation
[Br:1][C:2]1[N:3]=[CH:4][N:5]([CH2:7][C:8]2[CH:18]=[CH:17][C:11]3[N:12]=[C:13]([S:15][CH3:16])[S:14][C:10]=3[CH:9]=2)[CH:6]=1.ClC1C=C(C=CC=1)C(OO)=[O:24].C([O-])(O)=O.[Na+]>C(Cl)Cl>[Br:1][C:2]1[N:3]=[CH:4][N:5]([CH2:7][C:8]2[CH:18]=[CH:17][C:11]3[N:12]=[C:13]([S:15]([CH3:16])=[O:24])[S:14][C:10]=3[CH:9]=2)[CH:6]=1

Participants

5

Reactant 3

HCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 866810186-((4-bromo-1H-imidazol-1-yl)methyl)-2-(methylthio)benzo[d]thiazole

Product 1

HCID 866810196-((4-bromo-1H-imidazol-1-yl)methyl)-2-(methylsulfinyl)benzo[d]thiazoleYield 121.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred mixture of 6-((4-bromo-1H-imidazol-1-yl)methyl)-2-(methylthio)benzo[d]thiazole (105 mg, 0.3 mmol) from Step 5 of this Example in CH2Cl2 (15 mL) at 0° C. was added 70-75% 3-chloroperoxybenzoic acid (91 mg, 0.4 mmol). After the mixture was stirred at 0° C. for 2 h, saturated aq NaHCO3 (10 mL) was added. The mixture was stirred for 10 min and the CH2Cl2 layer was separated, dried over Na2SO4, filtered, and concentrated under reduced pressure to afford 6-((4-bromo-1H-imidazol-1-yl)methyl)-2-(methylsulfinyl)benzo[d]thiazole (130 mg) as a white foam. The material was used in the next step without further purification. LCMS (ESI) m/z 356 and 358 (M+H)+.

Workup

  1. customat 0° C.
  2. stirringThe mixture was stirred for 10 min
  3. customthe CH2Cl2 layer was separated
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-9a3746ebd365426e80a1578374fe26e3
Source dataset
uspto-grants-2015_02
Patent number
US08952058B2

Reaction notes

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