Water → HCID 18429306, compound

HRID 1280167Notes

Reaction equation

HRID 1280167 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:9]=[C:10]([N+:12]([O-:14])=[O:13])[CH:11]=1)[CH:7]=[CH2:8])([O-:3])=[O:2].[OH2:15]>C(#N)C>[N+:1]([C:4]1[CH:5]=[C:6]([CH2:7][CH2:8][OH:15])[CH:9]=[C:10]([N+:12]([O-:14])=[O:13])[CH:11]=1)([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 962WaterHCID 121925533,5-Dinitrostyrene

Product 1

HCID 18429306HCID 18429306, compoundYield 25%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

3,5-Dinitrostyrene (0.28 g, 1.43 mmol) was dissolved in acetonitrile (150 ml) and water (300 ml) was added. The mixture was poured into a photolysis apparatus and irradiated with an UV-lamp (HPK 125, Phillips) for 3 h. The organic solvent was evaporated and the aqueous phase extracted with methylene chloride (2×100 ml). The solvent was evaporated and the residue was purified by flash chromatography on a column of silica using heptane/ethyl acetate (1/1) as eluent. Evaporation of solvent gave 76 mg (25%) of a crystalline product.

Workup

  1. additionThe mixture was poured into a photolysis apparatus
  2. customirradiated with an UV-lamp (HPK 125, Phillips) for 3 h
  3. customThe organic solvent was evaporated
  4. extractionthe aqueous phase extracted with methylene chloride (2×100 ml)
  5. customThe solvent was evaporated
  6. customthe residue was purified by flash chromatography on a column of silica
  7. customEvaporation of solvent

Sources & evidence

ORD record
ord-bc391d0bb7c74fe696976ba9db6f0762
Source dataset
uspto-grants-2002_09
Patent number
US06448442B1

Reaction notes

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