Potassium Carbonate → HCID 178516792, Verbindung

HRID 916261Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 916261
[CH2:1]([O:8][C:9]([N:11]1[CH2:15][C:14](=[O:16])[N:13]=[C:12]1[NH2:17])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl:18][C:19]1[CH:26]=[C:25]([F:27])[CH:24]=[CH:23][C:20]=1[CH2:21]Br.C([O-])([O-])=O.[K+].[K+]>C(#N)C>[CH2:1]([O:8][C:9]([N:11]1[CH2:15][C:14](=[O:16])[N:13]=[C:12]1[NH:17][CH2:21][C:20]1[CH:23]=[CH:24][C:25]([F:27])=[CH:26][C:19]=1[Cl:18])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 27250621-(Bromomethyl)-2-chloro-4-fluorobenzeneHCID 150541832-Amino-4-oxo-4,5-dihydro-imidazole-1-carboxylic acid benzyl ester

Produkt 1

HCID 178516792HCID 178516792, VerbindungAusbeute 48,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

A suspension of 2-amino-4-oxo-4,5-dihydro-imidazole-1-carboxylic acid benzyl ester (93.2 mg, 0.40 mmol), 2-chloro-4-fluoro-benzylbromide (89.2 mg, 0.40 mmol) and K2CO3 (83.01 mg, 0.60 mmol) in acetonitrile (10 mL) was heated to reflux under argon for 1 hr. Cooled to r.t. and the reaction mixture was partitioned between EtOAc and water. The organic layer was dried over Na2SO4 and concentrated to give a residue which was triturated with EtOAc and filtered to give 2-(2-chloro-4-fluoro-benzylamino)-4-oxo-4,5-dihydro-imidazole-1-carboxylic acid benzyl ester as a white solid (73.0 mg, 48.7%).

Aufarbeitung

  1. temperaturewas heated
  2. temperatureto reflux under argon for 1 hr
  3. customthe reaction mixture was partitioned between EtOAc and water
  4. dry with materialThe organic layer was dried over Na2SO4
  5. concentrationconcentrated
  6. customto give a residue which
  7. customwas triturated with EtOAc
  8. filtrationfiltered

Quellen und Nachweise

ORD-Eintrag
ord-e783ac867334472a86ffe753f9f68116
Quelldatensatz
uspto-grants-2007_09
Patentnummer
US07268231B2

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