1,1'-Carbonyldiimidazole → Ethyl 4-(2-oxo-2,3-dihydro-1H-benzimidazol-1-yl)benzoate

HRID 1675774Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1675774
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9]1[CH:19]=[CH:18][C:12]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:11][CH:10]=1.[C:20](N1C=CN=C1)(N1C=CN=C1)=[O:21]>C1COCC1>[O:21]=[C:20]1[N:8]([C:9]2[CH:19]=[CH:18][C:12]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:11][CH:10]=2)[C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[NH:1]1

Komponenten

4

Edukt 2

HCID 682631,1'-CarbonyldiimidazoleHCID 18449398Ethyl 4-[(2-aminophenyl)amino]benzoate

Produkt 1

HCID 18449399Ethyl 4-(2-oxo-2,3-dihydro-1H-benzimidazol-1-yl)benzoate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
75 °C

Versuchsvorschrift

A mixture of ethyl 4-[(2-aminophenyl)amino]benzoate from Step B (442 mg, 1.72 mmol) and 1,1′-carbonyldiimidazole (652 mg, 4.02 mmol) in THF (10 mL) was heated at 75° C. for 3 h. The cooled mixture was partitioned between EtOAc (100 mL) and 10% aqueous citric acid (50 mL). The organic layer was washed with H2O (30 mL), then brine (30 mL), then dried over Na2SO4, filtered, and concentrated under reduced pressure. The crude product was purified by silica gel chromatography, eluting with a gradient of hexane:EtOAc-95:5 to 75:25, to give the title compound. MS: m/z=283 (M+1).

Aufarbeitung

  1. customThe cooled mixture was partitioned between EtOAc (100 mL) and 10% aqueous citric acid (50 mL)
  2. washThe organic layer was washed with H2O (30 mL)
  3. dry with materialbrine (30 mL), then dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe crude product was purified by silica gel chromatography
  7. washeluting with a gradient of hexane

Quellen und Nachweise

ORD-Eintrag
ord-9f7cc548c3994d988b6488f08873ad46
Quelldatensatz
uspto-grants-2011_08
Patentnummer
US08003792B2

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