4-Nitroanthranilic acid → HCID 10447733, Verbindung

HRID 567678

Reaktionsgleichung

Reaktionsgleichung von HRID 567678
[N+:1]([C:4]1[CH:5]=[C:6]([NH2:13])[C:7](=[CH:11][CH:12]=1)[C:8]([OH:10])=[O:9])([O-:3])=[O:2].[F:14][C:15]1[CH:23]=[CH:22][CH:21]=[C:20]([F:24])[C:16]=1[C:17](Cl)=O.C(N(CC)CC)C.C1(C)C=CC=CC=1.C(NC1C=CC2N=C(C3C(F)=CC=CC=3F)OC(=O)C=2C=1)(=O)C>C1COCC1>[F:14][C:15]1[CH:23]=[CH:22][CH:21]=[C:20]([F:24])[C:16]=1[C:17]1[O:9][C:8](=[O:10])[C:7]2[CH:11]=[CH:12][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][C:6]=2[N:13]=1

Komponenten

6

Edukt 4

HCID 120764-Nitroanthranilic acidHCID 874382,6-Difluorobenzoyl chlorideHCID 99488136-Acetamido-(2,6-difluoro-phenyl)-benzo[d][1,3]oxazin-4-oneHCID 22504574Toluene triethylamine

Produkt 1

HCID 10447733HCID 10447733, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

4-Nitroanthranilic acid (0.6 g), 2,6-difluorobenzoyl chloride (0.93 mL) and triethyl amine/toluene (1/1) (18 mL) were reacted as described under (10). reaction time 2 days. Extraction between ethyl acetate (100 mL) and HCl (2N, 100 mL), followed by separation of the organic layer, drylng over MgSO4, filtering and evaporation gave a crude product which was dissolved in warm THF (20 mL) and precipitated with hexane twice to get the pure product 2-(2,6-difluoro-phenyl)-7-nitro-benzo[d][1,3]oxazin-4-one (0.417 g), mp. 187 C, MS m/e: 304 M+.

Aufarbeitung

  1. customreaction time 2 days
  2. extractionExtraction between ethyl acetate (100 mL) and HCl (2N, 100 mL)
  3. customfollowed by separation of the organic layer
  4. filtrationfiltering
  5. customevaporation
  6. customgave a crude product which
  7. customprecipitated with hexane twice

Quellen und Nachweise

ORD-Eintrag
ord-ce17f9d856284bcd8eb7ba6a75536540
Quelldatensatz
uspto-grants-2001_01
Patentnummer
US06180625B2

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