Diisopropylethylamine → N-[2-(4-chlorophenyl)-2-oxoethyl]-N'-cyclopropylurea

HRID 660864Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 660864
Cl.[NH2:2][CH2:3][C:4]([C:6]1[CH:11]=[CH:10][C:9]([Cl:12])=[CH:8][CH:7]=1)=[O:5].[CH:13]1([N:16]=[C:17]=[O:18])[CH2:15][CH2:14]1.C(N(CC)C(C)C)(C)C>ClCCl>[Cl:12][C:9]1[CH:10]=[CH:11][C:6]([C:4](=[O:5])[CH2:3][NH:2][C:17]([NH:16][CH:13]2[CH2:15][CH2:14]2)=[O:18])=[CH:7][CH:8]=1

Komponenten

5

Edukt 3

HCID 81531DiisopropylethylamineHCID 637659IsocyanatocyclopropaneHCID 27982112-Amino-1-(4-chlorophenyl)ethan-1-one hydrochloride

Produkt 1

HCID 58011668N-[2-(4-chlorophenyl)-2-oxoethyl]-N'-cyclopropylurea

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel3×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

1000 mg (4.853 mmol) of 2-amino-1-(4-chlorophenyl)ethanone hydrochloride are placed in 20 ml dichloromethane, cooled to 0° C. and treated dropwise with a solution of 363 mg (4.367 mmol) of cyclopropyl isocyanate in 2 ml dichloromethane. It is stirred a further 10 mins at 0° C. and then a solution of 627 mg (4.853 mmol) of N,N-diisopropylethylamine in 4 ml dichloromethane is added dropwise. After two hours' stirring at room temperature the reaction mixture is evaporated and the crude product purified by flash chromatography on silica gel (eluent: dichloromethane/methanol 100:1). 1000 mg (73% of theory) of the target compound are obtained.

Aufarbeitung

  1. stirringAfter two hours' stirring at room temperature the reaction mixture
  2. customis evaporated
  3. customthe crude product purified by flash chromatography on silica gel (eluent: dichloromethane/methanol 100:1)
  4. custom1000 mg (73% of theory) of the target compound are obtained

Quellen und Nachweise

ORD-Eintrag
ord-898df1a07a834e19b27ce607529c941f
Quelldatensatz
uspto-grants-2011_12
Patentnummer
US08084481B2

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