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

HRID 2215580Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2215580
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-b2d57b0db43d419c90334ae4babe0c6f
Quelldatensatz
uspto-grants-2006_09
Patentnummer
US07109219B2

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