Toluene → N-[2-(2-methyl-5-nitro-1-imidazolyl)ethyl]-3-nitrophthalimide

HRID 1973446

Reaktionsgleichung

Reaktionsgleichung von HRID 1973446
[N+:1]([C:4]1[CH:14]=[CH:13][CH:12]=[C:6]2[C:7]([NH:9][C:10](=[O:11])[C:5]=12)=[O:8])([O-:3])=[O:2].[K].Cl[CH2:17][CH2:18][N:19]1[C:23]([N+:24]([O-:26])=[O:25])=[CH:22][N:21]=[C:20]1[CH3:27].C1(C)C=CC=CC=1>C(Cl)(Cl)Cl>[CH3:27][C:20]1[N:19]([CH2:18][CH2:17][N:9]2[C:10](=[O:11])[C:5]3=[C:4]([N+:1]([O-:3])=[O:2])[CH:14]=[CH:13][CH:12]=[C:6]3[C:7]2=[O:8])[C:23]([N+:24]([O-:26])=[O:25])=[CH:22][N:21]=1

Komponenten

6

Edukt 4

HCID 1140TolueneHCID 117793-NitrophthalimideHCID 832101-(2-Chloroethyl)-2-methyl-5-nitroimidazoleHCID 5462222Potassium

Produkt 1

HCID 21491667N-[2-(2-methyl-5-nitro-1-imidazolyl)ethyl]-3-nitrophthalimide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6212ChloroformLösungsmittel

Versuchsvorschrift

3-Nitrophthalimide is converted to the potassium salt by the procedure described in Example 13 and then reacted with 1-(2-chloroethyl)-2-methyl-5-nitroimidazole according to the procedure described in Example 1. The crude reaction mixture is digested with toluene and then filtered to remove some insoluble material. Evaporation of the solvent leaves a syrup which is diluted with chloroform and then filtered to remove some insoluble material. The filtrate is further diluted with toluene and again filtered to remove some precipitate. The solvent is then evaporated from the filtrate and the resulting residue is recrystallized first from ethanol and then from acetone to give N-[2-(2-methyl-5-nitro-1-imidazolyl)ethyl]-3-nitrophthalimide melting at about 175°-176° C.

Aufarbeitung

  1. customThe crude reaction mixture
  2. filtrationfiltered
  3. customto remove some insoluble material
  4. customEvaporation of the solvent
  5. customleaves a syrup which
  6. filtrationfiltered
  7. customto remove some insoluble material
  8. additionThe filtrate is further diluted with toluene
  9. filtrationagain filtered
  10. customto remove some precipitate
  11. customThe solvent is then evaporated from the filtrate
  12. customthe resulting residue is recrystallized first from ethanol

Quellen und Nachweise

ORD-Eintrag
ord-dc05d02bf81342b9a9572f3970f7d9fb
Quelldatensatz
uspto-grants-1976_12
Patentnummer
US03997572

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