5-(Dimethylamino)methyl-2-mercaptomethyl-4-methylthiophene → N-{2-[[5-(dimethylamino)methyl-4-methyl-2-thienyl]methylthio]ethyl}-N'-(beta-hydroxyphenethyl)-2-nitro-1,1-ethenediamine

HRID 236257Notes

Reaction equation

HRID 236257 reaction equation
[CH3:1][N:2]([CH2:4][C:5]1[S:9][C:8]([CH2:10][SH:11])=[CH:7][C:6]=1[CH3:12])[CH3:3].C[O-].[Na+].CO.Cl[CH2:19][CH2:20][NH:21][C:22]([NH:27][CH2:28][CH:29]([OH:36])[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)=[CH:23][N+:24]([O-:26])=[O:25]>CO>[CH3:3][N:2]([CH2:4][C:5]1[S:9][C:8]([CH2:10][S:11][CH2:19][CH2:20][NH:21][C:22]([NH:27][CH2:28][CH:29]([OH:36])[C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)=[CH:23][N+:24]([O-:26])=[O:25])=[CH:7][C:6]=1[CH3:12])[CH3:1]

Participants

5

Reactant 3

HCID 138252725-(Dimethylamino)methyl-2-mercaptomethyl-4-methylthiopheneHCID 23694274Sodium methanolate methanolHCID 67897400N-(2-chloroethyl)-N'-(beta-hydroxyphenethyl)-2-nitro-1,1-ethenediamine

Product 1

HCID 70357017N-{2-[[5-(dimethylamino)methyl-4-methyl-2-thienyl]methylthio]ethyl}-N'-(beta-hydroxyphenethyl)-2-nitro-1,1-ethenediamineYield 11%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In 5 ml of methanol was dissolved 0.14 g of 5-(dimethylamino)methyl-2-mercaptomethyl-4-methylthiophene, and 0.2 ml of a 3.57N sodium methoxide-methanol solution was added at room temperature in a nitrogen atomsphere, after which 0.2 g of N-(2-chloroethyl)-N'-(β-hydroxyphenethyl)-2-nitro-1,1-ethenediamine was added at one time, after which the reaction mixture was allowed to stand at room temperature for 24 hours, and the deposited substance was removed by filtration, after which the solvent was removed by distillation under reduced pressure. Chloroform was added to the resulting residue, and the insolubles were removed by filtration, after which the solvent was removed by distillation under reduced pressure, and the residue thus obtained was purified by a column chromatography (basic alumina, eluent; chloroform:methanol=10:1 by volume) to obtain 0.033 g (yield 11%) of N-{2-[[5-(dimethylamino)methyl-4-methyl-2-thienyl]methylthio]ethyl}-N'-(β-hydroxyphenethyl)-2-nitro-1,1-ethenediamine having a melting point of 114°-115° C.

Workup

  1. additionwas added at room temperature in a nitrogen atomsphere
  2. customthe deposited substance was removed by filtration
  3. customafter which the solvent was removed by distillation under reduced pressure
  4. additionChloroform was added to the resulting residue
  5. customthe insolubles were removed by filtration
  6. customafter which the solvent was removed by distillation under reduced pressure
  7. customthe residue thus obtained
  8. customwas purified by a column chromatography (basic alumina, eluent; chloroform:methanol=10:1 by volume)

Sources & evidence

ORD record
ord-550953e024b94c989a808e1f88eee096
Source dataset
uspto-grants-1987_02
Patent number
US04643849

Reaction notes

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