Diethyl Ether → 6-chloro-8-methoxy-1H-benzo[d][1,3]oxazine-2,4-dione

HRID 1186094Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1186094
[NH2:1][C:2]1[C:10]([O:11][CH3:12])=[CH:9][C:8]([Cl:13])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].Cl[C:15](Cl)([O:17]C(=O)OC(Cl)(Cl)Cl)Cl.C(OCC)C>O1CCCC1>[Cl:13][C:8]1[CH:9]=[C:10]([O:11][CH3:12])[C:2]2[NH:1][C:15](=[O:17])[O:5][C:4](=[O:6])[C:3]=2[CH:7]=1

Komponenten

5

Edukt 3

HCID 3283Diethyl EtherHCID 94429TriphosgeneHCID 545958742-Amino-5-chloro-3-methoxybenzoic acid

Produkt 1

HCID 866705806-chloro-8-methoxy-1H-benzo[d][1,3]oxazine-2,4-dione

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To 2-amino-5-chloro-3-methoxybenzoic acid (0.72 g, 3.57 mmol) in anhydrous tetrahydrofuran (15 mL) was added triphosgene (0.53 g, 1.8 mmol). The mixture was heated to refluxed under a nitrogen atmosphere for 2.5 hours. The resulting solution was cooled to ambient temperature, diethyl ether (10 mL) was added, which caused a solid to precipitate. The solid was collected by filtration and washed with more diethyl ether to yield 6-chloro-8-methoxy-1H-benzo[d][1,3]oxazine-2,4-dione. MS (m/z): 226.3, 228.3 (M+H)+.

Aufarbeitung

  1. temperatureThe mixture was heated
  2. temperatureto refluxed under a nitrogen atmosphere for 2.5 hours
  3. customto precipitate
  4. filtrationThe solid was collected by filtration
  5. washwashed with more diethyl ether

Quellen und Nachweise

ORD-Eintrag
ord-77b0c302418546b1a5642a4a9d4b7251
Quelldatensatz
uspto-grants-2014_03
Patentnummer
US08673897B2

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