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

HRID 2226900Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2226900
[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

Komponenten

5

Edukt 2

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 935NickelKatalysatorHCID 887MethanolLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-57ed9e033b3b49ae9a9814e0b7151af6
Quelldatensatz
uspto-grants-1994_09
Patentnummer
US05350757

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