Triethylamine hydrochloride → HCID 178466837, Verbindung

HRID 1096942Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1096942
[C:1]([C:3]1[CH:4]=[C:5]([CH:10]=[C:11]([O:13][CH2:14][CH3:15])[CH:12]=1)[C:6]([O:8][CH3:9])=[O:7])#[N:2].[N-:16]=[N+:17]=[N-:18].[Na+].Cl.C(N(CC)CC)C.[OH-].[Na+]>CN(C=O)C>[CH2:14]([O:13][C:11]1[CH:10]=[C:5]([CH:4]=[C:3]([C:1]2[NH:18][N:17]=[N:16][N:2]=2)[CH:12]=1)[C:6]([O:8][CH3:9])=[O:7])[CH3:15]

Komponenten

6

Edukt 4

HCID 11130Triethylamine hydrochlorideHCID 14798Sodium HydroxideHCID 33557Sodium AzideHCID 21942546Methyl 3-cyano-5-ethoxybenzoate

Produkt 1

HCID 178466837HCID 178466837, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

A mixture of methyl 3-cyano-5-ethoxybenzoate (182 mg, 0.89 mmol), sodium azide (173 mg, 2.66 mmol), triethylamine hydrochloride (366 mg, 2.66 mmol) and DMF (4.4 mL) was stirred in a nitrogen atmosphere at 100° C. for 12 hours. After left cooled, aqueous 5 N sodium hydroxide solution (0.53 mL, 2.66 mmol) was added to the reaction mixture, and washed with chloroform. The aqueous layer was made to have a pH of 2 with 5 N hydrochloric acid, and extracted with chloroform. The organic layer was dried with sodium sulfate, concentrated under reduced pressure, and the residue was purified through silica gel column chromatography to obtain the title compound as a colorless solid.

Aufarbeitung

  1. waitAfter left
  2. temperaturecooled
  3. washwashed with chloroform
  4. extractionextracted with chloroform
  5. dry with materialThe organic layer was dried with sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customthe residue was purified through silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-77615c0e4b284087aed63b72f96d5ab2
Quelldatensatz
uspto-grants-2012_03
Patentnummer
US08138197B2

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