Triethylamine → 4-methoxy-1H-benzo[d]imidazol-2(3H)-one

HRID 887458Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 887458
[NH2:1][C:2]1[C:10]([O:11][CH3:12])=[CH:9][CH:8]=[CH:7][C:3]=1C(O)=O.P(N=[N+]=[N-])(=O)([O:21][C:22]1C=CC=CC=1)OC1C=CC=CC=1.C([N:34](CC)CC)C>C1COCC1>[CH3:12][O:11][C:10]1[C:2]2[NH:1][C:22](=[O:21])[NH:34][C:3]=2[CH:7]=[CH:8][CH:9]=1

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 123414Diphenylphosphoryl azideHCID 2557202-Amino-3-methoxybenzoic acid

Produkt 1

HCID 129266284-methoxy-1H-benzo[d]imidazol-2(3H)-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To a round bottomed flask was added 2-amino-3-methoxybenzoic acid (2.2705 g, 13.58 mmol), diphenyl phosphorazidate (3.51 mL, 16.30 mmol), and triethylamine (3.79 mL, 27.2 mmol) in THF to stir at 80° C. Upon completion the reaction was allowed to cool to room temperature. Solvent was evaporated. The residue was taken up in DCM. The reaction mixture was diluted with water and extracted with DCM. A white precipitate was noted to form during extraction The solid was filtered to provide 4-methoxy-1H-benzo[d]imidazol-2(3H)-one. [M+H]=165.0.

Aufarbeitung

  1. temperatureto cool to room temperature
  2. customSolvent was evaporated
  3. additionThe reaction mixture was diluted with water
  4. extractionextracted with DCM
  5. customto form during extraction The solid
  6. filtrationwas filtered

Quellen und Nachweise

ORD-Eintrag
ord-6e70f2030da740e5a66d243bccb4c834
Quelldatensatz
uspto-grants-2012_08
Patentnummer
US08247418B2

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