2-Methoxyethylamine → N-2-(2-dimethylaminomethyl-4-thiazolylmethylthio)ethyl-N'-(2-methoxy)ethyl 2-nitro-1,1-ethenediamine

HRID 850939Notes

Reaction equation

HRID 850939 reaction equation
[CH3:1][N:2]([CH2:4][C:5]1[S:6][CH:7]=[C:8]([CH2:10][S:11][CH2:12][CH2:13][NH:14][C:15](SC)=[CH:16][N+:17]([O-:19])=[O:18])[N:9]=1)[CH3:3].[CH3:22][O:23][CH2:24][CH2:25][NH2:26]>C(O)C>[CH3:3][N:2]([CH2:4][C:5]1[S:6][CH:7]=[C:8]([CH2:10][S:11][CH2:12][CH2:13][NH:14][C:15]([NH:26][CH2:25][CH2:24][O:23][CH3:22])=[CH:16][N+:17]([O-:19])=[O:18])[N:9]=1)[CH3:1]

Participants

4

Reactant 2

HCID 80182-MethoxyethylamineHCID 678972721-[2-(2-Dimethylaminomethyl-4-thiazolylmethylthio)ethyl]amino-1-methylthio-2-nitroethylene

Product 1

HCID 70482832N-2-(2-dimethylaminomethyl-4-thiazolylmethylthio)ethyl-N'-(2-methoxy)ethyl 2-nitro-1,1-ethenediamine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A reaction mixture, prepared from 1.25 g of 1-[2-(2-dimethylaminomethyl-4-thiazolylmethylthio)ethyl]amino-1-methylthio-2-nitroethylene, 0.27 g of 2-methoxyethylamine and 20 ml of ethanol, was heated to refluxing temperature for about three hours. The solvent was then removed by evaporation and the resulting residue was chromatographed over silica using a gradient elution technique. The desired compound was eluted with a 5:95 methanol:ethyl acetate solvent mixture. Removal of the solvent yielded N-2-(2-dimethylaminomethyl-4-thiazolylmethylthio)ethyl-N'-(2-methoxy)ethyl 2-nitro-1,1-ethenediamine as an oil.

Workup

  1. temperaturewas heated
  2. temperatureto refluxing temperature for about three hours
  3. customThe solvent was then removed by evaporation
  4. customthe resulting residue was chromatographed over silica using
  5. washa gradient elution technique
  6. washThe desired compound was eluted with a 5:95 methanol
  7. customRemoval of the solvent

Sources & evidence

ORD record
ord-57bf7bf707df431d9f95720033a4c833
Source dataset
uspto-grants-1983_05
Patent number
US04382090

Reaction notes

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