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

HRID 1650204Notes

Reaction equation

HRID 1650204 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 678971645-(3-Methoxyphenyl)-2-nitromethyleneoxazolidine

Product 1

HCID 67897156N-{2-[[5-(dimethylamino)methyl-4-methyl-2-thienyl]methylthio]ethyl}-N'-[2-(3-methoxyphenyl)-2-hydroxyethyl]-2-nitro-1,1-ethenediamineYield 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-97051bcd7db84082933d80f8eca8f358
Source dataset
uspto-grants-1990_05
Patent number
US04923882

Reaction notes

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