Methyl iodide → 5-Bromo-2-(methylthio)benzo[d]thiazole

HRID 1944687Notes

Reaction equation

HRID 1944687 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[S:9][C:8]([SH:10])=[N:7][C:6]=2[CH:11]=1.[CH2:12](N(CC)CC)C.CI>CCO>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[S:9][C:8]([S:10][CH3:12])=[N:7][C:6]=2[CH:11]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 8471TriethylamineHCID 178527757HCID 178527757, compound

Product 1

HCID 28012715-Bromo-2-(methylthio)benzo[d]thiazoleYield 80%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 5-bromobenzo[d]thiazole-2-thiol (24 mg, 0.098 mmol) in EtOH (1.5 mL) was added triethylamine (10 mg, 0.098 mmol) and methyliodide (14 mg, 0.098 mmol). The mixture was heated at reflux for 1.5 h. Then the mixture was extracted with dichloromethane (3×10 mL). The combined organic extracts were washed with brine, dried (Na2SO4) and concentrated to give 5-bromo-2-(methylthio)benzothiazole 20 mg (80%).

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 1.5 h
  3. extractionThen the mixture was extracted with dichloromethane (3×10 mL)
  4. washThe combined organic extracts were washed with brine
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-45a1b769159946da840d57a52d26c256
Source dataset
uspto-grants-2013_03
Patent number
US08394842B2

Reaction notes

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