Methyl iodide → HCID 15580449, compound

HRID 615173Notes

Reaction equation

HRID 615173 reaction equation
[NH2:1][C:2]1[CH:19]=[CH:18][C:5]2[N:6]3[CH:11]=[C:10]([C:12]4[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=4)[N:9]=[C:7]3[S:8][C:4]=2[CH:3]=1.[CH3:20]I>C(O)C>[CH3:20][NH:1][C:2]1[CH:19]=[CH:18][C:5]2[N:6]3[CH:11]=[C:10]([C:12]4[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=4)[N:9]=[C:7]3[S:8][C:4]=2[CH:3]=1

Participants

4

Reactant 2

HCID 6328Methyl iodideHCID 15580438HCID 15580438, compound

Product 1

HCID 15580449HCID 15580449, compoundYield 9.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To 50 ml of ethanol were added 500 mg of 7-amino-2-phenylimidazo[2,1-b]benzothiazole, 265 mg of methyl iodide and 260 mg of potassium carbonate anhydride and while stirring vigorously, the mixture was refluxed for 2 days. The reaction mixture was cooled and then concentrated under reduced pressure. The residue was extracted with 50 ml of ethyl acetate and the extract was washed with water, dried with anhydrous magnesium sulfate, and then the extract was concentrated under reduced pressure. The residue was subjected to silica gel column chromatography (eluant: toluene:ethyl acetate=4:1) and the obtained crystals were recrystallized from toluene to provide 50 mg of 7-methylamino-2-phenylimidazo-[2,1-b]benzothiazole.

Workup

  1. temperaturethe mixture was refluxed for 2 days
  2. temperatureThe reaction mixture was cooled
  3. concentrationconcentrated under reduced pressure
  4. extractionThe residue was extracted with 50 ml of ethyl acetate
  5. washthe extract was washed with water
  6. dry with materialdried with anhydrous magnesium sulfate
  7. concentrationthe extract was concentrated under reduced pressure
  8. customthe obtained crystals were recrystallized from toluene

Sources & evidence

ORD record
ord-fc730d49d54c4fabbd97fb2ce9ff0f9b
Source dataset
uspto-grants-1985_02
Patent number
US04497817

Reaction notes

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