p-Toluenesulfonic acid monohydrate → 5-Hydroxy-2-[(2-oxo-1-imidazolidinyl)methyl]-4(1H)-pyridinone, p-toluenesulfonate salt

HRID 1252608Notes

Reaction equation

HRID 1252608 reaction equation
[O:1]=[C:2]1[NH:6][CH2:5][CH2:4][N:3]1[CH2:7][C:8]1[N:9](CC2C=CC=CC=2)[CH:10]=[C:11]([O:15]CC2C=CC=CC=2)[C:12](=[O:14])[CH:13]=1.O.[C:31]1([CH3:41])[CH:36]=[CH:35][C:34]([S:37]([OH:40])(=[O:39])=[O:38])=[CH:33][CH:32]=1.[H][H]>CN(C)C=O.[Pd]>[C:31]1([CH3:41])[CH:32]=[CH:33][C:34]([S:37]([OH:40])(=[O:38])=[O:39])=[CH:35][CH:36]=1.[OH:15][C:11]1[C:12](=[O:14])[CH:13]=[C:8]([CH2:7][N:3]2[CH2:4][CH2:5][NH:6][C:2]2=[O:1])[NH:9][CH:10]=1

Participants

6

Reactant 3

HCID 521998p-Toluenesulfonic acid monohydrateHCID 141824752-[(2-Oxo-1-imidazolidinyl)methyl]-5-(phenylmethoxy)-1-(phenylmethyl)-4(1H)-pyridinoneHCID 178418361HCID 178418361, compound

Product 1

HCID 141824775-Hydroxy-2-[(2-oxo-1-imidazolidinyl)methyl]-4(1H)-pyridinone, p-toluenesulfonate saltYield 84.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-[(2-oxo-1-imidazolidinyl)methyl]-5-(phenylmethoxy)-1-(phenylmethyl)-4(1H)pyridinone (4.98 g; 12.8 mmol) in dimethylformamide (90 ml) was added p-toluenesulfonic acid monohydrate (4.86 g; 25.6 mmol) and palladium on charcoal (1.0 g), and hydrogen was bubbled through the mixture for 30 minutes. The catalyst was filtered off by suction and the filtrate evaporated in vacuo. The residue was triturated with dichloromethane and ether, and the product filtered off by suction, yielding 4.12 g of the title compound, melting point 195° C.

Workup

  1. customwas bubbled through the mixture for 30 minutes
  2. filtrationThe catalyst was filtered off by suction
  3. customthe filtrate evaporated in vacuo
  4. customThe residue was triturated with dichloromethane and ether
  5. filtrationthe product filtered off by suction

Sources & evidence

ORD record
ord-e0ee885fda1641998dbd480f87c56258
Source dataset
uspto-grants-1988_05
Patent number
US04743685

Reaction notes

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