Tetrahydrofuran → Methyl 2-oxo-2,3-dihydro-1H-benzo[d]imidazole-4-carboxylate

HRID 1628379Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1628379
[NH2:1][C:2]1[C:11]([NH2:12])=[CH:10][CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].[O:13]1CCC[CH2:14]1>>[O:13]=[C:14]1[NH:12][C:11]2[CH:10]=[CH:9][CH:8]=[C:3]([C:4]([O:6][CH3:7])=[O:5])[C:2]=2[NH:1]1

Komponenten

3

Edukt 2

HCID 8028TetrahydrofuranHCID 5718252,3-Diaminobenzoic acid methyl ester

Produkt 1

HCID 22745204Methyl 2-oxo-2,3-dihydro-1H-benzo[d]imidazole-4-carboxylateAusbeute 94 %

Versuchsvorschrift

To a suspension of methyl 2,3-diaminobenzoate (32.9 g, 198 mmol) in tetrahydrofuran (300 mL) was added N,N′-carbonyldiimidazole (33.7 g, 208 mmol), and the mixture was stirred at room temperature for 15 hr. The solvent was evaporated in vacuo, and the residual solid was suspended in ethyl acetate (110 mL) and stirred at 80° C. After 30 min, the mixture was stirred at room temperature for 1 hr, and the resulting solid was collected by filtration and washed with ethyl acetate to give the title compound (35.6 g, 185 mmol, 94%) as a colorless solid.

Aufarbeitung

  1. customThe solvent was evaporated in vacuo
  2. stirringstirred at 80° C
  3. waitAfter 30 min
  4. stirringthe mixture was stirred at room temperature for 1 hr
  5. filtrationthe resulting solid was collected by filtration
  6. washwashed with ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-fd83d629636241ea8d2c71531f218065
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08785460B2

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