Methyl iodide → 5-Methoxy-2-(methylsulfanyl)-1,3-benzothiazole

HRID 1029356Notes

Reaction equation

HRID 1029356 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[S:10][C:9]([SH:11])=[N:8][C:7]=2[CH:12]=1.[CH2:13](N(CC)CC)C.IC>C(O)C.C(O)(C)C>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[S:10][C:9]([S:11][CH3:13])=[N:8][C:7]=2[CH:12]=1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 8471TriethylamineHCID 178488276HCID 178488276, compound

Product 1

HCID 199000125-Methoxy-2-(methylsulfanyl)-1,3-benzothiazoleYield 103.4%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 3776IsopropanolSolvent

Procedure

5-Methoxy-2-mercaptobenzothiazole (18.3 g, 0.1 mol) was dispersed in 125 ml 95% ethanol. Addition of 10.1 g (0.1 mol) triethylamine gave a brown solution. Addition of iodomethane (14.2 g, 0.1 mol) was slightly exothermic. Additional heating brought the mixture to reflux for 2 hours. After cooling, the residue was dispersed in isopropanol and filtered to remove triethylammonium iodide. The filtrate was mixed with water and the layers separated. The aqueous phase was extracted 3×50 ml methylene chloride. The organic portions were combined, washed and brine, and dried with Na2SO4. Filtration and rotary evaporation yielded 21.85 g brown liquid which was distilled at 158°-162° C. (0.125 mm) to give 16.73 g (85%).

Workup

  1. customgave a brown solution
  2. temperatureAdditional heating
  3. temperatureto reflux for 2 hours
  4. temperatureAfter cooling
  5. filtrationfiltered
  6. customto remove triethylammonium iodide
  7. additionThe filtrate was mixed with water
  8. customthe layers separated
  9. extractionThe aqueous phase was extracted 3×50 ml methylene chloride
  10. washwashed
  11. dry with materialbrine, and dried with Na2SO4
  12. filtrationFiltration and rotary evaporation

Sources & evidence

ORD record
ord-f728556a03c44d82b06238de9797d1b5
Source dataset
uspto-grants-1992_04
Patent number
US05102781

Reaction notes

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