Acetic Acid → HCID 59255370, Verbindung

HRID 1691063

Reaktionsgleichung

Reaktionsgleichung von HRID 1691063
[Cl:1][C:2]1[O:6][C:5]([CH2:7][C:8]2[CH:15]=[CH:14][C:11]([CH2:12]N)=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.C(O)(=[O:18])C.N([O-])=O.[Na+].C(=O)([O-])[O-].[K+].[K+]>C(OCC)(=O)C.O>[Cl:1][C:2]1[O:6][C:5]([CH2:7][C:8]2[CH:15]=[CH:14][C:11]([CH2:12][OH:18])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1

Komponenten

7

Edukt 4

HCID 176Acetic AcidHCID 11430Potassium CarbonateHCID 23668193Sodium NitriteHCID 592553974-(5-Chloro-furan-2-ylmethyl)-benzylamine

Produkt 1

HCID 59255370HCID 59255370, VerbindungAusbeute 44 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittel3×HCID 8857Ethyl AcetateLösungsmittel2×

Versuchsvorschrift

To a mixture of 4-(5-chloro-furan-2-ylmethyl)-benzylamine (2.6 g) described in Manufacturing Example 62-1-2, acetic acid (25 mL) and water (25 mL) was added sodium nitrite (9.8 g, 140 mmol) at 0° C., which was stirred for 40 minutes at room temperature. Water and ethyl acetate were added to extract the reaction mixture. The organic layer was washed successively with water, saturated sodium hydrogencarbonate and saturated aqueous sodium chloride, and the solvent was evaporated under a reduced pressure. Methanol (25 mL) was added to the residue at 0° C., followed by addition of potassium carbonate (3.3 g, 24 mmol) at the same temperature. This was stirred for 1 hour at the same temperature. Water and ethyl acetate were added to extract the reaction mixture. The organic layer was washed successively with water, saturated sodium hydrogencarbonate and saturated aqueous sodium chloride, and the organic layer was concentrated under a reduced pressure. The residue was purified by neutral silica gel column chromatography (ethyl acetate:heptane=1:2) to obtain the title compound (1.2 mg, 44%).

Aufarbeitung

  1. extractionto extract the reaction mixture
  2. washThe organic layer was washed successively with water, saturated sodium hydrogencarbonate and saturated aqueous sodium chloride
  3. customthe solvent was evaporated under a reduced pressure
  4. additionMethanol (25 mL) was added to the residue at 0° C.
  5. stirringThis was stirred for 1 hour at the same temperature
  6. extractionto extract the reaction mixture
  7. washThe organic layer was washed successively with water, saturated sodium hydrogencarbonate and saturated aqueous sodium chloride
  8. concentrationthe organic layer was concentrated under a reduced pressure
  9. customThe residue was purified by neutral silica gel column chromatography (ethyl acetate:heptane=1:2)

Quellen und Nachweise

ORD-Eintrag
ord-55743fa28a34413fab3dd88ffcf588fc
Quelldatensatz
uspto-grants-2012_04
Patentnummer
US08153662B2

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