Nitroethane → 1-Methylsulfanyl-4-(2-nitro-propenyl)-benzene

HRID 462697Notes

Reaction equation

HRID 462697 reaction equation
[CH3:1][S:2][C:3]1[CH:10]=[CH:9][C:6]([CH:7]=O)=[CH:5][CH:4]=1.[N+:11]([CH2:14][CH3:15])([O-:13])=[O:12].C(N)CCC>C(O)C>[CH3:1][S:2][C:3]1[CH:10]=[CH:9][C:6]([CH:7]=[C:14]([N+:11]([O-:13])=[O:12])[CH3:15])=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 6587NitroethaneHCID 8007ButylamineHCID 769854-(Methylthio)benzaldehyde

Product 1

HCID 28259171-Methylsulfanyl-4-(2-nitro-propenyl)-benzeneYield 44.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The intermediate 1-[4-(methylthio)phenyl]-2-nitro-1-propene was prepared as follows: [U.S. Pat. No. 3,117,160, Example V]; a mixture containing 15.2 g of 4-(methylthio)benzaldehyde, 7.5 g of nitroethane, 0.73 g of n-butylamine and 40 ml of absolute ethanol was refluxed with stirring for 21 hours and the solvent then removed by distilling in vacuo. The residue was recrystallized from absolute ethanol (total volume of 60 ml) washed with a small quantity of cold ethanol and dried in vacuo at room temperature to produce 9.3 g of 1-[4-(methylthio)phenyl]-2-nitro-1-propene, m.p. 74°-76° C.

Workup

  1. customThe intermediate 1-[4-(methylthio)phenyl]-2-nitro-1-propene was prepared
  2. temperaturewas refluxed
  3. customthe solvent then removed
  4. distillationby distilling in vacuo
  5. customThe residue was recrystallized from absolute ethanol (total volume of 60 ml)
  6. washwashed with a small quantity of cold ethanol
  7. customdried in vacuo at room temperature

Sources & evidence

ORD record
ord-e7dc28bb41c44a029e109f4229f2e877
Source dataset
uspto-grants-1985_05
Patent number
US04517192

Reaction notes

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