Hydrochloric Acid → 4-[2-(2,5-Dioxoimidazolidin-1-yl)ethoxy]-3-methoxy-2-nitrobenzaldehyde

HRID 1821430Notes

Reaction equation

HRID 1821430 reaction equation
CO[CH:3]([O:19]C)[C:4]1[CH:13]=[CH:12][C:7]([O:8][CH2:9][CH2:10][NH2:11])=[C:6]([O:14][CH3:15])[C:5]=1[N+:16]([O-:18])=[O:17].C(N(CC)CC)C.[N+:28]([CH2:30][C:31]([O:33]CC)=O)#[C-:29].Cl.[OH-:37].[Na+]>C1COCC1.CC(C)=O.O>[O:37]=[C:29]1[NH:28][CH2:30][C:31](=[O:33])[N:11]1[CH2:10][CH2:9][O:8][C:7]1[CH:12]=[CH:13][C:4]([CH:3]=[O:19])=[C:5]([N+:16]([O-:18])=[O:17])[C:6]=1[O:14][CH3:15]

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 533707Ethyl isocyanoacetateHCID 689994632-(4-Dimethoxymethyl-2-methoxy-3-nitrophenoxy)ethylamine

Product 1

HCID 866282204-[2-(2,5-Dioxoimidazolidin-1-yl)ethoxy]-3-methoxy-2-nitrobenzaldehydeYield 42%

Reagents, catalysts & solvents 3

HCID 180AcetoneSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2-(4-dimethoxymethyl-2-methoxy-3-nitrophenoxy)ethylamine (0.16 g, 0.56 mmol) obtained in Step 3 of Example 338 in THF (5.0 mL) was added with triethylamine (0.23 mL, 1.7 mmol) and ethyl isocyanoacetate (0.09 mL, 0.84 mmol), followed by stirring at room temperature for 1 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 to obtain crude product. The product was added with a mixed solvent of acetone (2.0 mL) and 6 mol/L hydrochloric acid (1.0 ml) and heated under reflux for 2.5 hours. The reaction mixture was neutralized by 2 mol/L aqueous sodium hydroxide solution and then 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 to obtain 4-[2-(2,5-dioxoimidazolidin-1-yl)ethoxy]-3-methoxy-2-nitrobenzaldehyde (0.08 g, 42%).

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. customto obtain crude product
  6. temperatureheated
  7. temperatureunder reflux for 2.5 hours
  8. extractionextracted with ethyl acetate
  9. washThe organic layer was washed with saturated brine
  10. dry with materialdried over anhydrous magnesium sulfate
  11. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-70ccbd5cb41d406d90ff55eb38e0f3b3
Source dataset
uspto-grants-2009_10
Patent number
US07605272B2

Reaction notes

Loading…