5,5-Diphenylhydantoin → 3-[2-(2-Methyl-5-nitro-1-imidazolyl)ethyl]-5,5-diphenylhydantoin

HRID 1973443

Reaktionsgleichung

Reaktionsgleichung von HRID 1973443
Cl[CH2:2][CH2:3][N:4]1[C:8]([N+:9]([O-:11])=[O:10])=[CH:7][N:6]=[C:5]1[CH3:12].[Na].[C:14]1([C:20]2([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[NH:24][C:23](=[O:25])[NH:22][C:21]2=[O:26])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.CN(C)C=O>CCOCC.C1(C)C=CC=CC=1.CO>[CH3:12][C:5]1[N:4]([CH2:3][CH2:2][N:22]2[C:21](=[O:26])[C:20]([C:27]3[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=3)([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[NH:24][C:23]2=[O:25])[C:8]([N+:9]([O-:11])=[O:10])=[CH:7][N:6]=1

Komponenten

8

Edukt 4

HCID 17755,5-DiphenylhydantoinHCID 6228DimethylformamideHCID 832101-(2-Chloroethyl)-2-methyl-5-nitroimidazoleHCID 5360545Sodium

Produkt 1

HCID 214916623-[2-(2-Methyl-5-nitro-1-imidazolyl)ethyl]-5,5-diphenylhydantoin

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 887MethanolLösungsmittelHCID 1140TolueneLösungsmittelHCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

1.4 Parts of 1-(2-chloroethyl)-2-methyl-5-nitroimidazole is mixed with 2.5 parts of the sodium salt of 5,5-diphenylhydantoin and 75 parts of dimethylformamide is added under nitrogen. The mixture is heated on a steam bath for 1 hour and then 10 parts of methanol is added and heating is continued for an additional 4 hours. The solvent is then evaporated on the steam bath under a stream of nitrogen to leave a residual mixture of solid and oil. The residue is mixed with toluene and filtered to remove some insoluble material. The toluene solution is diluted to a volume of 250 parts and washed with a mixture of 25 parts of sodium bicarbonate and 120 parts of water. The toluene solution is then washed with water and dried over magnesium sulfate and the solvent is evaporated to leave a solid residue. This is digested in warm ether and then cooled and the solid is separated by filtration. The solid is recrystallized from ethanol to give 3-[2-(2-methyl-5 -nitro-1-imidazolyl)ethyl]-5,5-diphenylhydantoin melting at about 209°-210.5° C. This compound has the following formula ##STR8##

Aufarbeitung

  1. additionis added under nitrogen
  2. temperatureThe mixture is heated on a steam bath for 1 hour
  3. temperatureheating
  4. customThe solvent is then evaporated on the steam bath under a stream of nitrogen
  5. customto leave
  6. additiona residual mixture of solid and oil
  7. filtrationfiltered
  8. customto remove some insoluble material
  9. additionThe toluene solution is diluted to a volume of 250 parts
  10. washwashed with a mixture of 25 parts of sodium bicarbonate and 120 parts of water
  11. washThe toluene solution is then washed with water
  12. dry with materialdried over magnesium sulfate
  13. customthe solvent is evaporated
  14. customto leave a solid residue
  15. temperaturecooled
  16. customthe solid is separated by filtration
  17. customThe solid is recrystallized from ethanol

Quellen und Nachweise

ORD-Eintrag
ord-0a374b24630d4ac4b5faf421d94ab167
Quelldatensatz
uspto-grants-1976_12
Patentnummer
US03997572

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