5-[(3-Phenylmethoxy-4-methoxyphenyl)methylene]-2,4-imidazolidinedione → (RS)-5-[[4-Methoxy-3-(phenylmethoxy)phenyl]methyl]-2,4-imidazolidinedione

HRID 2395847Notes

Reaction equation

HRID 2395847 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]=[C:10]2[NH:14][C:13](=[O:15])[NH:12][C:11]2=[O:16])=[CH:5][C:4]=1[O:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.[H][H]>CO.[Ni]>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH:10]2[NH:14][C:13](=[O:15])[NH:12][C:11]2=[O:16])=[CH:5][C:4]=1[O:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

5

Reactant 2

HCID 538290325-[(3-Phenylmethoxy-4-methoxyphenyl)methylene]-2,4-imidazolidinedioneHCID 178418361HCID 178418361, compound

Product 1

HCID 15296732(RS)-5-[[4-Methoxy-3-(phenylmethoxy)phenyl]methyl]-2,4-imidazolidinedioneYield 47%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

A solution of 16.20 g (0.05 mole) of the benzylidene hydantoin from Example 4 in 100 mL of methanol and 25.0 g (0. 055 mole) of 20% tetramethylammonium hydroxide-in-methanol is reduced with hydrogen and Raney nickel catalyst. After the theoretical uptake of hydrogen the mixture is filtered and acetic acid (ca 5 mL) and then water is added until just turbid. The first crop of solid is filtered. This is starting material. An additional 2 L of water is added to precipitate the product as crop 2; wt 7.60 g (47% yield). Recrystallization from methanol gives pure product; mp 155°-157° C. Anal. Calc. for C18H18N2O4 : C, 66.24; H, 5.56; N, 8.59. Found: C, 66.19; H, 5.60; N, 8.68.

Workup

  1. filtrationAfter the theoretical uptake of hydrogen the mixture is filtered
  2. additionacetic acid (ca 5 mL) and then water is added until just turbid
  3. filtrationThe first crop of solid is filtered
  4. additionAn additional 2 L of water is added
  5. customto precipitate the product as crop 2
  6. customRecrystallization from methanol
  7. customgives pure product

Sources & evidence

ORD record
ord-36d019e201c94a49b29a511d6decf658
Source dataset
uspto-grants-1996_02
Patent number
US05489686

Reaction notes

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