Methylamine → Methyl (E)-4-{4-((1-methylamino-2-nitroethen-1-yl)amino)phenyl}-3-butenoate

HRID 373929Notes

Reaction equation

HRID 373929 reaction equation
CS[C:3]([NH:8][C:9]1[CH:14]=[CH:13][C:12](/[CH:15]=[CH:16]/[CH2:17][C:18]([O:20][CH3:21])=[O:19])=[CH:11][CH:10]=1)=[CH:4][N+:5]([O-:7])=[O:6].[CH3:22][NH2:23]>CO>[CH3:22][NH:23][C:3]([NH:8][C:9]1[CH:14]=[CH:13][C:12](/[CH:15]=[CH:16]/[CH2:17][C:18]([O:20][CH3:21])=[O:19])=[CH:11][CH:10]=1)=[CH:4][N+:5]([O-:7])=[O:6]

Participants

4

Reactant 2

HCID 6329MethylamineHCID 86746355Methyl (E)-4-{4-((1-methylthio-2-nitroethen-1-yl)amino)phenyl}-3-butenoate

Product 1

HCID 86746356Methyl (E)-4-{4-((1-methylamino-2-nitroethen-1-yl)amino)phenyl}-3-butenoateYield 54%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

1.00 g of methyl (E)-4-{4-((1-methylthio-2-nitroethen-1-yl)amino)phenyl}-3-butenoate was suspended in 5 ml of methanol, followed by the addition of 1.25 ml of a 40% solution of methylamine in methanol. The obtained mixture was stirred at a room temperature for 4 hours and distilled to remove the solvent. The residue was purified by silica gel column chromatography [solvent: dichloromethane/methanol (30:1)] to obtain 0.5 g of the title compound as a pale yellow solid (yield: 54%).

Workup

  1. distillationdistilled
  2. customto remove the solvent
  3. customThe residue was purified by silica gel column chromatography [solvent: dichloromethane/methanol (30:1)]

Sources & evidence

ORD record
ord-b3f389c764b942f68720007893f7fd8f
Source dataset
uspto-grants-1992_11
Patent number
US05166188

Reaction notes

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