Hydrochloric Acid → 6-Acetamido-(2,6-difluoro-phenyl)-benzo[d][1,3]oxazin-4-one

HRID 567676

Reaktionsgleichung

Reaktionsgleichung von HRID 567676
[C:1]([NH:4][C:5]1[CH:13]=[C:9]([C:10]([OH:12])=[O:11])[C:8]([NH2:14])=[CH:7][CH:6]=1)(=[O:3])[CH3:2].[F:15][C:16]1[CH:24]=[CH:23][CH:22]=[C:21]([F:25])[C:17]=1[C:18](Cl)=O.FC1C=CC=C(F)C=1C1OC(=O)C2C=C([N+]([O-])=O)C=CC=2N=1.Cl>C(N(CC)CC)C.C1(C)C=CC=CC=1.C(OCC)(=O)C>[C:1]([NH:4][C:5]1[CH:6]=[CH:7][C:8]2[N:14]=[C:18]([C:17]3[C:16]([F:15])=[CH:24][CH:23]=[CH:22][C:21]=3[F:25])[O:11][C:10](=[O:12])[C:9]=2[CH:13]=1)(=[O:3])[CH3:2]

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 874382,6-Difluorobenzoyl chlorideHCID 170890Benzoic acid, 5-(acetylamino)-2-amino-HCID 212624642-(2,6-Difluoro-phenyl)-6-nitro-benzo[d][1,3]oxazin-4-one

Produkt 1

HCID 99488136-Acetamido-(2,6-difluoro-phenyl)-benzo[d][1,3]oxazin-4-oneAusbeute 94 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8857Ethyl AcetateLösungsmittelHCID 22504574Toluene triethylamineLösungsmittel

Versuchsvorschrift

5-Acetamidoanthranilic acid (0.64g) and 2,6-difluorobenzoyl chloride (1.3 g) were reacted in triethyl amine/toluene (1/1) (20 mL) like described for compound (9), reaction time 1 h. Ethyl acetate (50 mL) and HCl-solution (1 mL 4N in 50 mL water) were added resulting in the formation of a precipitate.The mixture was filtered and the residue dissolved in THF followed by evaporation to dryness, subsequent dissolution in hot dioxane followed by precipitation with hexane resulted in colourless crystals of 6-acetamido-(2,6-difluoro-phenyl)-benzo[d][1,3]oxazin-4-one (0.98 g), mp.246 C, MS m/e.: 316 M+.

Aufarbeitung

  1. customresulting in the formation of a precipitate.The mixture
  2. filtrationwas filtered
  3. dissolutionthe residue dissolved in THF
  4. customfollowed by evaporation to dryness, subsequent dissolution in hot dioxane
  5. customfollowed by precipitation with hexane

Quellen und Nachweise

ORD-Eintrag
ord-3e485fe52fe24eaab6bc8b1cb4ca842a
Quelldatensatz
uspto-grants-2001_01
Patentnummer
US06180625B2

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