Aziridine → HCID 67897156, compound

HRID 236260

Reaction equation

HRID 236260 reaction equation
[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]

Participants

6

Reactant 3

HCID 9033AziridineHCID 13825272HCID 13825272, compoundHCID 67897164HCID 67897164, compound

Product 1

HCID 67897156HCID 67897156, compoundYield 83.8%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent3×HCID 6344DichloromethaneSolvent

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-963b92fb10944371ba15777abffa5a54
Source dataset
uspto-grants-1987_02
Patent number
US04643849

Linked notes

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