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

HRID 1821430
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HRID 1821430 반응식
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]
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참가 물질

9

반응물 5

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

생성물 1

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

시약·촉매·용매 3

HCID 180Acetone용매HCID 962Water용매HCID 8028Tetrahydrofuran용매

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-70ccbd5cb41d406d90ff55eb38e0f3b3
출처 데이터셋
uspto-grants-2009_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07605272B2

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