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

HRID 1973443

반응식

HRID 1973443 반응식
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

참가 물질

8

반응물 4

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

생성물 1

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

시약·촉매·용매 3

HCID 887Methanol용매HCID 1140Toluene용매HCID 3283Diethyl Ether용매

실험 절차

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##

후처리

  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

출처 및 근거

ORD 기록
ord-0a374b24630d4ac4b5faf421d94ab167
출처 데이터셋
uspto-grants-1976_12
특허 번호
US03997572

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