Water → (E)-3-(2-{4-[2-(1H-indazol-3-yl)vinyl]-2-methoxy-3-nitrophenoxy}ethyl)imidazolidine 2,4-dione

HRID 1821431Notes

Reaction equation

HRID 1821431 reaction equation
[Br-].[NH:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([CH2:11][P+](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=[N:3]1.[O:31]=[C:32]1[NH:36][CH2:35][C:34](=[O:37])[N:33]1[CH2:38][CH2:39][O:40][C:41]1[CH:48]=[CH:47][C:44]([CH:45]=O)=[C:43]([N+:49]([O-:51])=[O:50])[C:42]=1[O:52][CH3:53].C(=O)([O-])[O-].[K+].[K+].O>CO>[NH:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](/[CH:11]=[CH:45]/[C:44]2[CH:47]=[CH:48][C:41]([O:40][CH2:39][CH2:38][N:33]3[C:34](=[O:37])[CH2:35][NH:36][C:32]3=[O:31])=[C:42]([O:52][CH3:53])[C:43]=2[N+:49]([O-:51])=[O:50])=[N:3]1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 866282204-[2-(2,5-Dioxoimidazolidin-1-yl)ethoxy]-3-methoxy-2-nitrobenzaldehydeHCID 178419401HCID 178419401, compound

Product 1

HCID 68999904(E)-3-(2-{4-[2-(1H-indazol-3-yl)vinyl]-2-methoxy-3-nitrophenoxy}ethyl)imidazolidine 2,4-dioneYield 32%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

(1H-indazol-3-ylmethyl)triphenylphosphonium bromide (0.12 g, 0.26 mmol), 4-[2-(2,5-dioxoimidazolidin-1-yl)ethoxy]-3-methoxy-2-nitrobenzaldehyde (0.08 g, 0.24 mmol) obtained in Step 1 and potassium carbonate (0.07 g, 0.47 mmol) were dissolved in methanol (3.0 mL), followed by stirring at room temperature for 1.0 hour. The reaction mixture was added with water and extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (chloroform/methanol=9/1) to obtain (E)-3-(2-{4-[2-(1H-indazol-3-yl)vinyl]-2-methoxy-3-nitrophenoxy}ethyl)imidazolidine 2,4-dione (0.03 g, 32%).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (chloroform/methanol=9/1)

Sources & evidence

ORD record
ord-2c385d7573f24af69fbc97c8f1a59bd0
Source dataset
uspto-grants-2009_10
Patent number
US07605272B2

Reaction notes

Loading…