Methyl iodide → HCID 178470168, compound

HRID 2093064Notes

Reaction equation

HRID 2093064 reaction equation
[NH:1]([C:8]([N:10]1[CH2:15][CH2:14][C:13]2[N:16]=[C:17]([C:19]([O:21][CH2:22][CH3:23])=[O:20])[S:18][C:12]=2[CH2:11]1)=[S:9])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:24]([O-])([O-])=O.[K+].[K+].IC>CC(C)=O>[CH3:24][S:9]/[C:8](=[N:1]\[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)/[N:10]1[CH2:15][CH2:14][C:13]2[N:16]=[C:17]([C:19]([O:21][CH2:22][CH3:23])=[O:20])[S:18][C:12]=2[CH2:11]1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 86650190Ethyl 5-(anilinocarbonothioyl)-4,5,6,7-tetrahydro[1,3]thiazolo[5,4-c]pyridine-2-carboxylate

Product 1

HCID 178470168HCID 178470168, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of ethyl 5-(anilinocarbonothioyl)-4,5,6,7-tetrahydro[1,3]thiazolo[5,4-c]pyridine-2-carboxylate obtained in step I (1 eq) in acetone, K2CO3 (1.2 eq) was added and the reaction mixture was stirred for 15 min. To this, iodomethane (1.2 eq) was added and the reaction was continued at room temperature for 5 h. Solvent was evaporated and the residue was diluted dichloromethane. It was then washed with water and the organic layer was separated, dried over anhydrous Na2SO4 and concentrated under reduced pressure to afford crude product, which, on purification by column chromatography afforded the ethyl 5-[(Z)(methylthio)(phenylimino)methyl]-4,5,6,7-tetrahydro[1,3]thiazolo[5,4-c]pyridine-2-carboxylate.

Workup

  1. waitthe reaction was continued at room temperature for 5 h
  2. customSolvent was evaporated
  3. washIt was then washed with water
  4. customthe organic layer was separated
  5. dry with materialdried over anhydrous Na2SO4
  6. concentrationconcentrated under reduced pressure
  7. customto afford crude product, which
  8. customon purification by column chromatography

Sources & evidence

ORD record
ord-520c620d4e254cb5bcc05c50752b19f8
Source dataset
uspto-grants-2013_05
Patent number
US08440830B2

Reaction notes

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