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Aziridine → N-{2-[[5-(dimethylamino)methyl-4-methyl-2-thienyl]methylthio]ethyl}-N'-[2-(3-methoxyphenyl)-2-hydroxyethyl]-2-nitro-1,1-ethenediamine

HRID 236260
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 236260
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]2[O:13][C:12](=[CH:14][N+:15]([O-:17])=[O:16])[NH:11][CH2:10]2)[CH:6]=[CH:7][CH:8]=1.[CH3:18][N:19]([CH2:21][C:22]1[S:26][C:25]([CH2:27][SH:28])=[CH:24][C:23]=1[CH3:29])[CH3:20].[CH2:30]1[NH:32][CH2:31]1>C(Cl)Cl.CO>[CH3:20][N:19]([CH2:21][C:22]1[S:26][C:25]([CH2:27][S:28][CH2:30][CH2:31][NH:32][C:12]([NH:11][CH2:10][CH:9]([C:5]2[CH:6]=[CH:7][CH:8]=[C:3]([O:2][CH3:1])[CH:4]=2)[OH:13])=[CH:14][N+:15]([O-:17])=[O:16])=[CH:24][C:23]=1[CH3:29])[CH3:18]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 3

HCID 9033AziridineHCID 138252725-(Dimethylamino)methyl-2-mercaptomethyl-4-methylthiopheneHCID 678971645-(3-Methoxyphenyl)-2-nitromethyleneoxazolidine

Produkt 1

HCID 67897156N-{2-[[5-(dimethylamino)methyl-4-methyl-2-thienyl]methylthio]ethyl}-N'-[2-(3-methoxyphenyl)-2-hydroxyethyl]-2-nitro-1,1-ethenediamineAusbeute 83,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887
Methanol
Lösungsmittel
3×
HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

In a mixed solvent of 20 ml of methylene chloride and 10 ml of methanol was dissolved 2.4 g of 5-(3-methoxyphenyl)-2-nitromethyleneoxazolidine at room temperature, and a solution of 2.0 g of 5-(dimethylamino)methyl-2-mercaptomethyl-4-methylthiophene in 5 ml of methanol was added thereto in a nitrogen atmosphere. Then, the solution of 0.5 g of ethyleneimine in 5 ml of methanol was added dropwise at the same temperature over a period of 10 minutes. After addition, the resulting solution was subjected to reaction with stirring for 5 hours. After the completion of the reaction, the solvent was removed by distillation under reduced pressure, and the residue obtained was purified by a column chromatography (Wako Silica Gel C-200, eluent; chloroform:ethanol=30:1 by volume) to obtain 4.0 g (yield 83.5%) of oily N-{2-[[5-(dimethylamino)methyl-4-methyl-2-thienyl]methylthio]ethyl}-N'-[2-(3-methoxyphenyl)-2-hydroxyethyl]-2-nitro-1,1-ethenediamine.

Aufarbeitung

  1. additionAfter addition
  2. customthe resulting solution was subjected to reaction
  3. customAfter the completion of the reaction
  4. customthe solvent was removed by distillation under reduced pressure
  5. customthe residue obtained
  6. customwas purified by a column chromatography (Wako Silica Gel C-200, eluent; chloroform:ethanol=30:1 by volume)

Quellen und Nachweise

ORD-Eintrag
ord-963b92fb10944371ba15777abffa5a54
Quelldatensatz
uspto-grants-1987_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04643849

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