Triethylamine → N-(2-chloro-4-fluorophenyl)-2-cyanoacetamide

HRID 2095799Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2095799
[Cl:1][C:2]1[CH:8]=[C:7]([F:9])[CH:6]=[CH:5][C:3]=1[NH2:4].[C:10]([CH2:12][C:13](O)=[O:14])#[N:11].CN(C)CCCN=C=NCC.Cl.N1(O)C2C=CC=CC=2N=N1.C(N(CC)CC)C>C(OCC)(=O)C.CN(C)C=O>[Cl:1][C:2]1[CH:8]=[C:7]([F:9])[CH:6]=[CH:5][C:3]=1[NH:4][C:13](=[O:14])[CH2:12][C:10]#[N:11]

Komponenten

8

Edukt 5

HCID 8471TriethylamineHCID 9740Cyanoacetic acidHCID 75013Benzenamine, 2-chloro-4-fluoro-HCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Produkt 1

HCID 3644962N-(2-chloro-4-fluorophenyl)-2-cyanoacetamideAusbeute 55 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A mixture of 2-chloro-4-fluoroaniline (3.55 g, 24.3 mmol), cyanoacetic acid (2.48 g, 29.2 mmol), N-[3-(dimethylamino)propyl]-N′-ethylcarbodiimide•hydrochloride (7.01 g, 36.5 mmol), 1H-1,2,3-benzotriazol-1-ol (4.94 g, 36.5 mmol), triethylamine (5.10 mL, 36.5 mmol) and N,N-dimethylformamide (50 mL) was stirred at room temperature for 16 hr. The mixture was diluted with ethyl acetate, washed with water, saturated aqueous sodium hydrogen carbonate solution and saturated brine, dried over anhydrous magnesium sulfate, and filtered through a basic silica gel pad. The solvent was evaporated under reduced pressure, and the obtained residue was washed with hexane and collected by filtration to give the title compound (2.84 g, 54%) as a white solid.

Aufarbeitung

  1. washwashed with water, saturated aqueous sodium hydrogen carbonate solution and saturated brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. filtrationfiltered through a basic silica gel pad
  4. customThe solvent was evaporated under reduced pressure
  5. washthe obtained residue was washed with hexane
  6. filtrationcollected by filtration

Quellen und Nachweise

ORD-Eintrag
ord-2cbd6a2d32d94a978ef05bae026b8dee
Quelldatensatz
uspto-grants-2013_05
Patentnummer
US08445509B2

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