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

HRID 1821430
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1821430
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]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

9

Edukt 5

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 180AcetoneLösungsmittelHCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

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%).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-70ccbd5cb41d406d90ff55eb38e0f3b3
Quelldatensatz
uspto-grants-2009_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07605272B2

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