HCID 21401472, compound → HCID 21401469, compound

HRID 973147Notes

Reaction equation

HRID 973147 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([N:11]2[C:15](=[O:16])[C:14](=[O:17])[N:13]([C:18]3[CH:23]=[CH:22][C:21]([C:24]([O:26][CH3:27])=[O:25])=[CH:20][CH:19]=3)[C:12]2=[CH2:28])=[CH:7][CH:6]=1)=[O:4].[H][H]>CN(C)C=O.[Pd]>[CH3:27][O:26][C:24]([C:21]1[CH:22]=[CH:23][C:18]([N:13]2[C:14](=[O:17])[C:15](=[O:16])[N:11]([C:8]3[CH:9]=[CH:10][C:5]([C:3]([O:2][CH3:1])=[O:4])=[CH:6][CH:7]=3)[CH:12]2[CH3:28])=[CH:19][CH:20]=1)=[O:25]

Participants

5

Reactant 2

HCID 21401472HCID 21401472, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 21401469HCID 21401469, compoundYield 83.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6228DimethylformamideSolvent

Procedure

A solution of 40.8 g (0.1 mole) of 1,3-bis-(4'-methoxycarbonylphenyl)-2-methylene-imidazolidine-4,5-dione in 500 ml of dimethylformamide is hydrogenated in a laboratory hydrogenating apparatus, after addition of 2 g of a 5% palladium on charcoal catalyst, at room temperature and with vigorous stirring under slight hydrogen overpressure, until the uptake of hydrogen has ceased. The catalyst is filtered off and the solution is poured into 3 liters of ice water with vigorous stirring. The precipitated product is recrystallised from xylene, to yield 32 g of colourless crystals with a melting point of 250° C. The IR and NMR spectra confirm the presumed structure.

Workup

  1. filtrationThe catalyst is filtered off
  2. additionthe solution is poured into 3 liters of ice water with vigorous stirring
  3. customThe precipitated product is recrystallised from xylene

Sources & evidence

ORD record
ord-5dc31a191c68497cb19b68f97f4a59c9
Source dataset
uspto-grants-1977_10
Patent number
US04055570

Reaction notes

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