Acetic Acid → 3-chloro-2-((E)-nitropropenyl)thiophene

HRID 450703Notes

Reaction equation

HRID 450703 reaction equation
[Cl:1][C:2]1[CH:6]=[CH:5][S:4][C:3]=1[CH:7]=O.[N+:9]([CH2:12][CH3:13])([O-:11])=[O:10].C([O-])(=O)C.[NH4+].C(O)(=O)C>C(OC(=O)C)C>[Cl:1][C:2]1[CH:6]=[CH:5][S:4][C:3]=1/[CH:7]=[CH:13]/[CH2:12][N+:9]([O-:11])=[O:10]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 6587NitroethaneHCID 517165Ammonium AcetateHCID 27358253-Chlorothiophene-2-carbaldehyde

Product 1

HCID 684982433-chloro-2-((E)-nitropropenyl)thiophene

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
90 °C

Procedure

In a sulfonation flask, a mixture containing 11.7 g (0.08 mol) 3-chlorothiophene-2-carbaldehyde, 48 g (0.64 mol) nitroethane, 15.4 g (0.2 mol) ammoniumacetate and 160 ml acetic acid is heated at 90° C. for 5 hours. After cooling ethylacetate is added and the organic phase washed three times with water. The organic phase is dried over sodium sulphate and after filtration the organic solvent is distilled off in a water jet vacuum. The residue is purified by column chromatography over silicagel (eluent: ethylacetate/heptane 1:5). Yield: 10.8 g (67% of theory) of a colourless oil (1H-NMR: 2.57/s/3H, 7.12/d/1H, 7.62/d/1H, 8.45/s/1H).

Workup

  1. additionis added
  2. washthe organic phase washed three times with water
  3. dry with materialThe organic phase is dried over sodium sulphate
  4. filtrationafter filtration the organic solvent
  5. distillationis distilled off in a water jet vacuum
  6. customThe residue is purified by column chromatography over silicagel (eluent: ethylacetate/heptane 1:5)

Sources & evidence

ORD record
ord-6354ab9964f442548c4b7335e0d66d23
Source dataset
uspto-grants-2013_07
Patent number
US08486986B2

Reaction notes

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