1,1-Bis(methylthio)-2-nitroethylene → Methyl (E)-4-{4-((1-methylthio-2-nitroethen-1-yl)amino)phenyl}-3-butenoate

HRID 1647235Notes

Reaction equation

HRID 1647235 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5](/[CH:8]=[CH:9]/[CH2:10][C:11]([O:13][CH3:14])=[O:12])=[CH:4][CH:3]=1.[CH3:15][S:16][C:17](SC)=[CH:18][N+:19]([O-:21])=[O:20]>C(O)CC>[CH3:15][S:16][C:17]([NH:1][C:2]1[CH:3]=[CH:4][C:5](/[CH:8]=[CH:9]/[CH2:10][C:11]([O:13][CH3:14])=[O:12])=[CH:6][CH:7]=1)=[CH:18][N+:19]([O-:21])=[O:20]

Participants

4

Reactant 2

HCID 836231,1-Bis(methylthio)-2-nitroethyleneHCID 68346334Methyl (E)-4-(4-aminophenyl)-3-butenoate

Product 1

HCID 86746355Methyl (E)-4-{4-((1-methylthio-2-nitroethen-1-yl)amino)phenyl}-3-butenoateYield 86%

Reagents, catalysts & solvents 1

HCID 10311-PropanolSolvent

Procedure

7.00 g of methyl (E)-4-(4-aminophenyl)-3-butenoate was dissolved in 120 ml of n-propanol, followed by the addition of 30.28 g of 1,1-bis(methylthio)-2-nitroethylene. The obtained mixture was heated under reflux for 3 hours and distilled to remove the solvent. The residue was purified by silica gel column chromatography (solvent: dichloromethane). The obtained solid was washed with ethyl ether to obtain 9.65 g of the title compound as a yellow powder (yield: 86%).

Workup

  1. temperatureThe obtained mixture was heated
  2. temperatureunder reflux for 3 hours
  3. distillationdistilled
  4. customto remove the solvent
  5. customThe residue was purified by silica gel column chromatography (solvent: dichloromethane)
  6. washThe obtained solid was washed with ethyl ether

Sources & evidence

ORD record
ord-4bf89326124848f48c7c2537dcd9052b
Source dataset
uspto-grants-1995_07
Patent number
US05430059

Reaction notes

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