Methyl iodide → HCID 15684611, compound

HRID 728166Notes

Reaction equation

HRID 728166 reaction equation
[CH3:1]I.[CH3:3][C:4]1[N:8]2[CH:9]=[CH:10][C:11]([CH3:13])=[CH:12][C:7]2=[N:6][C:5]=1[CH2:14][CH2:15][C:16]1[CH:25]=[CH:24][C:19]2[N:20]=[C:21]([S-:23])[O:22][C:18]=2[CH:17]=1.[K+]>CO>[CH3:3][C:4]1[N:8]2[CH:9]=[CH:10][C:11]([CH3:13])=[CH:12][C:7]2=[N:6][C:5]=1[CH2:14][CH2:15][C:16]1[CH:25]=[CH:24][C:19]2[N:20]=[C:21]([S:23][CH3:1])[O:22][C:18]=2[CH:17]=1

Participants

4

Reactant 2

HCID 6328Methyl iodideHCID 23676529HCID 23676529, compound

Product 1

HCID 15684611HCID 15684611, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Methyl iodide (0.38 ml) was added dropwise to a solution of potassium 6-[2-(3,7-dimethylimidazo[1,2-a]-pyridin-2-yl)ethyl]-2-benzoxazolethiolate (2.00 g) in methanol (30 ml) under ice-water cooling. After being stirred for 3 hours keeping the temperature below 5° C., the solvent was evaporated in vacuo. The residue was mixed with water and extracted with ethyl acetate. The extract was washed with water, dried over magnesium sulfate and evaporated in vacuo. The residue was recrystallized from a mixture of ethyl acetate and n-hexane to give 6-[2-(3,7-dimethylimidazo[1,2-a]pyridin-2-yl)ethyl]-2-methylthiobenzoxazole (1.31 g).

Workup

  1. customthe temperature below 5° C.
  2. customthe solvent was evaporated in vacuo
  3. additionThe residue was mixed with water
  4. extractionextracted with ethyl acetate
  5. washThe extract was washed with water
  6. dry with materialdried over magnesium sulfate
  7. customevaporated in vacuo
  8. customThe residue was recrystallized from a mixture of ethyl acetate and n-hexane

Sources & evidence

ORD record
ord-2308fa7b7b5a432c95421952efdaaaf3
Source dataset
uspto-grants-1991_09
Patent number
US05047411

Reaction notes

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