Hydrochloric Acid → HCID 15552091, Verbindung

HRID 587053Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 587053
[OH-].[Na+].[CH:3]([N:6]1C[CH2:9][CH2:8][C:7]1=O)([CH3:5])[CH3:4].Cl.[C:13](=[O:16])([O-])[O-:14].[Na+].[Na+].[Br:19][C:20]1[CH:21]=[CH:22][C:23](F)=[C:24]([CH:27]=1)[CH:25]=[O:26]>CS(C)=O>[Br:19][C:20]1[CH:21]=[CH:22][C:23]([N:6]([CH:3]([CH3:5])[CH3:4])[CH2:7][CH2:8][CH2:9][C:13]([OH:14])=[O:16])=[C:24]([CH:25]=[O:26])[CH:27]=1

Komponenten

7

Edukt 5

HCID 313Hydrochloric Acid2×HCID 10340Sodium CarbonateHCID 14798Sodium HydroxideHCID 77392N-IsopropylbutyrolactamHCID 7363275-Bromo-2-fluorobenzaldehyde

Produkt 1

HCID 15552091HCID 15552091, VerbindungAusbeute 7,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

4N sodium hydroxide (36 ml) was added to 1-isopropyl-2-pyrrolidone (9.2 g), and the mixture was stirred for 3.5 hours. After cooled to 0° C., the mixture was neutralized with concentrated hydrochloric acid. After sodium carbonate (15.3 g) was added thereto, a solution of 5-bromo-2-fluorobenzaldehyde (7.3 g) in dimethyl sulfoxide (96 ml) was added thereto, and the mixture was heated to reflux for 5 hours. After cooled to room temperature, pH was adjusted to approximate 4 with 6N hydrochloric acid, and the mixture was extracted with ethyl acetate/THF. The extract was washed with saturated brine and dried with magnesium sulfate. The solvent was removed under reduced pressure, and the resulting residue was purified with silica gel column chromatography (hexane/ethyl acetate=4/1→3/2) to give 4-(4-bromo-2-formylisopropylanilino)butyric acid (0.92 g).

Aufarbeitung

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 5 hours
  3. temperatureAfter cooled to room temperature
  4. extractionthe mixture was extracted with ethyl acetate/THF
  5. washThe extract was washed with saturated brine
  6. dry with materialdried with magnesium sulfate
  7. customThe solvent was removed under reduced pressure
  8. customthe resulting residue was purified with silica gel column chromatography (hexane/ethyl acetate=4/1→3/2)

Quellen und Nachweise

ORD-Eintrag
ord-e17d7eef7a4547969de5e0a5055c0b58
Quelldatensatz
uspto-grants-2005_08
Patentnummer
US06936602B1

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