Triethylamine → 1-(4-Fluoro-phenyl)-4-methyl-2-oxo-imidazolidine-4-carboxylic acid (4-cyano-3-trifluoromethyl-phenyl)-amide

HRID 491765Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 491765
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:12][C:11]([CH3:16])([C:13]([OH:15])=O)[NH:10][C:9]2=[O:17])=[CH:4][CH:3]=1.C(Cl)(=O)C(Cl)=O.[NH2:24][C:25]1[CH:32]=[CH:31][C:28]([C:29]#[N:30])=[C:27]([C:33]([F:36])([F:35])[F:34])[CH:26]=1.C(N(CC)CC)C>C(Cl)Cl.CN(C=O)C>[C:29]([C:28]1[CH:31]=[CH:32][C:25]([NH:24][C:13]([C:11]2([CH3:16])[CH2:12][N:8]([C:5]3[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=3)[C:9](=[O:17])[NH:10]2)=[O:15])=[CH:26][C:27]=1[C:33]([F:34])([F:35])[F:36])#[N:30]

Komponenten

7

Edukt 4

HCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 5221704-Amino-2-(trifluoromethyl)benzonitrileHCID 441926221-(4-Fluorophenyl)-4-methyl-2-oxoimidazolidine-4-carboxylic acid

Produkt 1

HCID 116328381-(4-Fluoro-phenyl)-4-methyl-2-oxo-imidazolidine-4-carboxylic acid (4-cyano-3-trifluoromethyl-phenyl)-amideAusbeute 54,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideKatalysatorHCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

A solution of 1-(4-fluoro-phenyl)-4-methyl-2-oxo-imidazolidine-4-carboxylic acid (120 mg, 0.50 mmol) in DCM (15 mL) was treated oxalyl chloride (0.09 mL, 1.03 mmol) and one drop of dry DMF. After stirring 1 hour at room temperature, the solvent was removed in vacuo. To this residue, a solution of 4-amino-2-(trifluoromethyl)benzonitrile (277 mg, 1.49 mmol) and triethylamine (0.28 mL, 2.01 mmol) in dry DCM (10 mL) was added. After stirring overnight at room temperature, the mixture was concentrated in vacuo and the residue purified by flash chromatography to afford the title compound as a tan solid (110 mg, 54%).

Aufarbeitung

  1. customthe solvent was removed in vacuo
  2. stirringAfter stirring overnight at room temperature
  3. concentrationthe mixture was concentrated in vacuo
  4. customthe residue purified by flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-53a53a0a0dcc4c399b13c80204e6a00f
Quelldatensatz
uspto-grants-2009_05
Patentnummer
US07531565B2

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