Methyl iodide → N-Methyl-1,3-benzothiazol-6-amine

HRID 2260634Notes

Reaction equation

HRID 2260634 reaction equation
FC(F)(F)[C:3]([NH:5][C:6]1[CH:14]=[CH:13][C:9]2[N:10]=[CH:11][S:12][C:8]=2[CH:7]=1)=O.CI.[OH-].[K+]>CC(C)=O>[CH3:3][NH:5][C:6]1[CH:14]=[CH:13][C:9]2[N:10]=[CH:11][S:12][C:8]=2[CH:7]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 14797Potassium HydroxideHCID 18998810HCID 18998810, compound

Product 1

HCID 10630860N-Methyl-1,3-benzothiazol-6-amineYield 19%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To 6-Trifluoroacetamidobenzothiazole (1.97 g, 8 mmol) in 40 ml dry acetone was added methyl iodide (4.54 g, 32 mmol) and then KOH (2.1 g, 32 mmol). The mixture was refluxed for 40 min. and concentrated in vacuo. The product was taken up in 40 ml H2O, refluxed for 40 min. and extracted with methylene chloride. The organic phase was washed with water, dried over Na2SO4 and concentrated in vacuo. The product was purified by flash chromatography (silica gel, methylene chloride) to give 250 mg 6-methylamino-benzothiazole.

Workup

  1. temperatureThe mixture was refluxed for 40 min.
  2. concentrationconcentrated in vacuo
  3. temperaturerefluxed for 40 min.
  4. extractionextracted with methylene chloride
  5. washThe organic phase was washed with water
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated in vacuo
  8. customThe product was purified by flash chromatography (silica gel, methylene chloride)

Sources & evidence

ORD record
ord-3cac699a41a841f3ba23cbb621c2d77f
Source dataset
uspto-grants-1995_12
Patent number
US05478845

Reaction notes

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