Ethanol → N'-(3-hydroxyphenethyl)-2-nitro-1,1-ethenediamine

HRID 892795Notes

Reaction equation

HRID 892795 reaction equation
C[N:2](CC1SC=C(CSCCN)N=1)C.[N+:15]([CH:18]=[C:19]1[NH:23][CH2:22][CH:21]([C:24]2[CH:29]=[CH:28]C=C[CH:25]=2)O1)([O-:17])=[O:16].[CH2:30]([OH:32])[CH3:31]>>[OH:32][C:30]1[CH:25]=[C:24]([CH:29]=[CH:28][CH:31]=1)[CH2:21][CH2:22][NH:23][C:19]([NH2:2])=[CH:18][N+:15]([O-:17])=[O:16]

Participants

4

Reactant 3

HCID 702EthanolHCID 109773182-(Dimethylaminomethyl)-4-(2-aminoethylthiomethyl)thiazoleHCID 678971662-Nitromethylene-5-phenyl-oxazolidine

Product 1

HCID 131717425N'-(3-hydroxyphenethyl)-2-nitro-1,1-ethenediamine

Procedure

With 2 ml of ethanol was mixed 1 g of 2-{[2-(dimethylamino)methyl-4-thiazolyl]methylthio}ethylamine and 1.1 g of 2-nitromethylene-5-phenyl-oxazolidine, and the resulting mixture was subjected to reaction under reflux for 1 hour. After completion of the reaction, the reaction mixture was filtered with cooling, and the solvent was removed by distillation under reduced pressure, after which the resulting residue was purified by a column chromatography (Wako Silica Gel C-200, eluent: chloroform:ethanol=20:1 by volume) to obtain 1.3 g (yield 68%) of N-{2-[[2-(dimethylamino)methyl-4-thiazolyl]methylthio]ethyl}-(dimethylamino)methyl-4-thiazolyl]methylthio]ethyl}-N'-(3-hydroxyphenethyl)-2-nitro-1,1-ethenediamine having a melting point of 100°-101° C.

Workup

  1. customthe resulting mixture was subjected to reaction
  2. temperatureunder reflux for 1 hour
  3. customAfter completion of the reaction
  4. filtrationthe reaction mixture was filtered
  5. temperaturewith cooling
  6. customthe solvent was removed by distillation under reduced pressure
  7. customafter which the resulting residue was purified by a column chromatography (Wako Silica Gel C-200, eluent: chloroform:ethanol=20:1 by volume)

Sources & evidence

ORD record
ord-e904055c259945f5b36d912ca8077f36
Source dataset
uspto-grants-1992_06
Patent number
US05120746

Reaction notes

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