1,1'-Carbonyldiimidazole → 5-Nitro-2,3-dihydro-1,3-benzoxazol-2-one

HRID 1665629

Reaktionsgleichung

Reaktionsgleichung von HRID 1665629
C1N=CN([C:6]([N:8]2C=N[CH:10]=[CH:9]2)=[O:7])C=1.NC1C=[C:18]([N+:20]([O-:22])=[O:21])[CH:17]=[CH:16][C:15]=1[OH:23]>CN(C=O)C>[N+:20]([C:18]1[CH:17]=[CH:16][C:15]2[O:23][C:6](=[O:7])[NH:8][C:9]=2[CH:10]=1)([O-:22])=[O:21]

Komponenten

4

Edukt 2

HCID 682631,1'-CarbonyldiimidazoleHCID 36133892-Amino-4-Nitrophenol

Produkt 1

HCID 2639655-Nitro-2,3-dihydro-1,3-benzoxazol-2-oneAusbeute 434,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

CDI (1.57 g, 19.4 mmol) was added at 0° C. to a stirred solution of 2-amino-4-nitro-phenol (500 mg, 0.6 mmol) in DMF (5 mL) and the resultant was stirred for 30 mins. The mixture was poured onto ice and stirred for 10 minutes. The resulting precipitate was isolated by filtration to afford 470 mg (80%) of 5-nitro-3H-benzooxazol-2-one. 1H NMR: (DMSO-d6): δ 12.4 (b s, 1H), 8.05 (dd, 1H), 7.85 (d, 1H), 7.54 (d, 1H).

Aufarbeitung

  1. additionThe mixture was poured onto ice
  2. stirringstirred for 10 minutes
  3. customThe resulting precipitate was isolated by filtration

Quellen und Nachweise

ORD-Eintrag
ord-66cc9ab9580b43b8b5b3e58bb58aee97
Quelldatensatz
uspto-grants-2011_10
Patentnummer
US08039463B2

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