Methyl iodide → HCID 178503545, compound

HRID 2222581Notes

Reaction equation

HRID 2222581 reaction equation
[NH:1]1[C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[C:3]([CH:10]=[C:11]2[S:15][C:14](=[S:16])[NH:13][C:12]2=[O:17])=[CH:2]1.[CH3:18]I>[OH-].[Na+].CO>[CH3:18][S:16][C:14]1[S:15][C:11](=[CH:10][C:3]2[C:4]3[C:5](=[N:6][CH:7]=[CH:8][CH:9]=3)[NH:1][CH:2]=2)[C:12](=[O:17])[N:13]=1

Participants

5

Reactant 2

HCID 6328Methyl iodideHCID 178518565HCID 178518565, compound

Product 1

HCID 178503545HCID 178503545, compoundYield 96.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

To a solution of 5-(1H-pyrrolo[2,3-b]pyridin-3-ylmethylene)-2-thioxo-1,3-thiazolidin-4-one (8 g, 30.6 mmol) in 12.6% aq. NaOH (12 mL) and methanol (80 mL), methyl iodide (2.25 mL, 36 mmol) was added and the reaction mixture stirred at RT for 4 h. Most of the solvent was distilled off and the precipitate was filtered and washed first with water, then with diethylether. The washings were concentrated and extracted with dichloromethane, dried over sodium sulphate and joined to the first solid crop. The whole crop was suspended in methanol, stirred 30′, filtered and dried to yield 2-(methylthio)-5-(1H-pyrrolo[2,3-b]pyridin-3-ylmethylene)-1,3-thiazol-4(5H)-one as a yellow solid (8.15 g, 29.5 mmol, 96%).

Workup

  1. distillationMost of the solvent was distilled off
  2. filtrationthe precipitate was filtered
  3. washwashed first with water
  4. concentrationThe washings were concentrated
  5. extractionextracted with dichloromethane
  6. dry with materialdried over sodium sulphate
  7. stirringstirred 30′,
  8. filtrationfiltered
  9. customdried

Sources & evidence

ORD record
ord-f2c80ca45b9b43e9a983dbde8b15a754
Source dataset
uspto-grants-2008_05
Patent number
US07371862B2

Reaction notes

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