Pyridinium → HCID 22144514, compound

HRID 1824790Notes

Reaction equation

HRID 1824790 reaction equation
O[C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[CH:4][C:3]=1[NH:10][C:11]([CH:13]1[CH2:17][S:16][C:15](=[O:18])[NH:14]1)=[O:12].[NH+]1C=CC=CC=1>CC1C=CC(C)=CC=1.C(OCC)(=O)C.O>[CH3:9][O:8][C:6]1[CH:5]=[CH:4][C:3]2[N:10]=[C:11]([CH:13]3[CH2:17][S:16][C:15](=[O:18])[NH:14]3)[O:12][C:2]=2[CH:7]=1

Participants

6

Reactant 2

HCID 4989215PyridiniumHCID 86605165HCID 86605165, compound

Product 1

HCID 22144514HCID 22144514, compoundYield 90%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 7809P-XyleneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To 2-oxo-thiazolidine-4-carboxylic acid (2-hydroxy-4-methoxy-phenyl)-amide (50 mg) in p-xylene (3 mL) was added pyridinium p-toluenesolfonate (42 mg). The reaction mixture was refluxed for 2 h and then allowed to cool to room temperature. The mixture was diluted with ethyl acetate and water was added. The layers were separated and the organic layer was washed with brine, dried (Na2SO4), and concentrated. Flash chromatography on silica gel eluting with 3% methanol-methylene chloride afforded 42 mg (90%) of the title compound as a solid. MS: 251 (MH+) HPLC tR: 1.60 min.

Workup

  1. temperatureThe reaction mixture was refluxed for 2 h
  2. additionwas added
  3. customThe layers were separated
  4. washthe organic layer was washed with brine
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-963d0468c4ac4aeea2c48be6ce0d065d
Source dataset
uspto-grants-2006_05
Patent number
US07045539B2

Reaction notes

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