Dimethylformamide → 2-(4-formylphenoxy)-N-methylacetamide

HRID 230123

Reaktionsgleichung

Reaktionsgleichung von HRID 230123
[CH:1]([C:3]1[CH:13]=[CH:12][C:6]([O:7][CH2:8][C:9](O)=[O:10])=[CH:5][CH:4]=1)=[O:2].[CH3:14][N:15](C=O)C.C(Cl)(=O)C(Cl)=O>C(Cl)Cl>[CH:1]([C:3]1[CH:13]=[CH:12][C:6]([O:7][CH2:8][C:9]([NH:15][CH3:14])=[O:10])=[CH:5][CH:4]=1)=[O:2]

Komponenten

5

Edukt 3

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 89177Acetic acid, 2-(4-formylphenoxy)-

Produkt 1

HCID 152705192-(4-formylphenoxy)-N-methylacetamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

2-(4-formylphenoxy)acetic acid was suspended in 20 mL of DCM at 0° C., and 0.5 mL of DMF was added followed by the dropwise addition of oxalyl chloride. The solution was allowed to warm to room temperature with stirring until gas evolution stopped and the solution was homogeneous. The solution containing the crude acid chloride was concentrated under vacuum and the residue resuspended in DCM, cooled to 0° C., and methylamine and DIEA were added. The mixture was allowed to warm to room temperature with stirring over 12 hours. The reaction mixture was then poured into 5% HCl, washed 3 times with EtOAc, dried over sodium sulfate, filtered and concentrated to a thick brown oil which was purified by column using DMC/MeOH to afford 2-(4-formylphenoxy)-N-methylacetamide (9) as an off white solid. NMR (CDCl3, 400 mHz), d═9.9 (1H, s), 7.88 (2H, d, J=8.6 Hz), 7.04 (2H, d, J=8.6 Hz), 6.6-6.5 (1H, BS, 4.54 (2H, s), 2.93 (3H, d, J=4.7 Hz).

Aufarbeitung

  1. concentrationwas concentrated under vacuum
  2. temperaturecooled to 0° C.
  3. additionmethylamine and DIEA were added
  4. temperatureto warm to room temperature
  5. stirringwith stirring over 12 hours
  6. additionThe reaction mixture was then poured into 5% HCl
  7. washwashed 3 times with EtOAc
  8. dry with materialdried over sodium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated to a thick brown oil which
  11. customwas purified by column

Quellen und Nachweise

ORD-Eintrag
ord-42d66c4839a14e6cbde5bd17cf1f9a11
Quelldatensatz
uspto-grants-2009_07
Patentnummer
US07566716B2

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