2-(Dimethylaminomethyl)-4-(2-aminoethylthiomethyl)thiazole → N-{2-[[2-(dimethylamino)methyl-4-thiazolyl]methylthio]ethyl}-N'-(beta-hydroxyphenethyl)-2-nitro-1,1-ethenediamine

HRID 1650208Notes

Reaction equation

HRID 1650208 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][NH2:14])[N:9]=1)[CH3:3].[N+:15]([CH:18]=[C:19]1[NH:23][CH2:22][CH:21]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[O:20]1)([O-:17])=[O:16]>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:19]([NH:23][CH2:22][CH:21]([OH:20])[C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)=[CH:18][N+:15]([O-:17])=[O:16])[N:9]=1)[CH3:1]

Participants

4

Reactant 2

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

Product 1

HCID 70357019N-{2-[[2-(dimethylamino)methyl-4-thiazolyl]methylthio]ethyl}-N'-(beta-hydroxyphenethyl)-2-nitro-1,1-ethenediamineYield 68.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

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}-N'-(β-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-51173d3a837d405f821ceac716dbe54f
Source dataset
uspto-grants-1990_05
Patent number
US04923882

Reaction notes

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