N,N-Diethyl-1,3-propanediamine → 1-(4-Chloropyridin-2-yl)-3-(3-diethylaminopropyl)urea

HRID 2376905Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2376905
C1(OC(=O)[N:9]([C:19]2[CH:24]=[C:23]([Cl:25])[CH:22]=[CH:21][N:20]=2)[C:10]([O:12]C2C=CC=CC=2)=O)C=CC=CC=1.[CH2:27]([N:29]([CH2:34][CH3:35])[CH2:30][CH2:31][CH2:32][NH2:33])[CH3:28]>CN(C)C=O>[Cl:25][C:23]1[CH:22]=[CH:21][N:20]=[C:19]([NH:9][C:10]([NH:33][CH2:32][CH2:31][CH2:30][N:29]([CH2:34][CH3:35])[CH2:27][CH3:28])=[O:12])[CH:24]=1

Komponenten

4

Edukt 2

HCID 61011N,N-Diethyl-1,3-propanediamineHCID 21054897Phenyl (4-chloropyridin-2-yl)-N-(phenoxycarbonyl)carbamate

Produkt 1

HCID 219490931-(4-Chloropyridin-2-yl)-3-(3-diethylaminopropyl)ureaAusbeute 54,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

Phenyl(4-chloropyridin-2-yl)-N-(phenoxycarbonyl)carbamate (738 mg, 2.00 mmol) was dissolved in N,N-dimethylformamide (8.0 ml); N,N-diethyl-1,3-diaminopropane (1.57 ml, 10.0 mmol) was added thereto; and the reaction mixture was stirred at room temperature for 1 hour. The reaction mixture was partitioned between water and ethyl acetate; and the organic layer was washed with brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (Fuji Silysia NH, hexane-ethyl acetate-methanol system) to yield the title compound (309 mg, 1.09 mmol, 54.3%) as a pale brown oil.

Aufarbeitung

  1. customThe reaction mixture was partitioned between water and ethyl acetate
  2. washand the organic layer was washed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (Fuji Silysia NH, hexane-ethyl acetate-methanol system)

Quellen und Nachweise

ORD-Eintrag
ord-738fd3eed3174f5e92b41a788f5824cb
Quelldatensatz
uspto-grants-2008_12
Patentnummer
US07468380B2

Notizen zur Reaktion

Wird geladen…