Acetic Acid → 5,7-dichloro-2,4-dihydro-1H-3,1-benzoxazine-2,4-dione

HRID 3103

Reaktionsgleichung

Reaktionsgleichung von HRID 3103
[Cl:1][C:2]1[CH:10]=[C:9]([Cl:11])[CH:8]=[C:7]2[C:3]=1[C:4](=[O:13])[C:5](=[O:12])[NH:6]2.C(O)(=[O:16])C>C(OC(=O)C)(=O)C.O.[O-2].[O-2].[O-2].[Cr+6]>[Cl:1][C:2]1[C:3]2[C:4](=[O:13])[O:12][C:5](=[O:16])[NH:6][C:7]=2[CH:8]=[C:9]([Cl:11])[CH:10]=1

Komponenten

6

Edukt 2

HCID 176Acetic AcidHCID 2519084,6-Dichloroisatin

Produkt 1

HCID 123632155,7-dichloro-2,4-dihydro-1H-3,1-benzoxazine-2,4-dioneAusbeute 72 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 10219390chromium (VI) trioxideKatalysator2×HCID 962WaterLösungsmittelHCID 7918Acetic AnhydrideLösungsmittel

Versuchsvorschrift

To a stirred solution of 4,6-dichloro-1H-indole-2,3-dione (5.00 g, 23.2 mM) in acetic acid (21 mL) and acetic anhydride (21 mL) at 80° C. was added in small portions chromium trioxide (4.12 g, 41.3 mM). The temperature of the reaction mixture was maintained between 80°-90° C. during the addition of the chromium trioxide. After the addition was complete, the reaction mixture was diluted with water (100 mL) and then filtered to separate the precipitated solids. The solids were washed thoroughly with water and then dried to obtain the title compound as a yellow solid (4.13 g, 72%); MS(CI): 232 (M+H).

Aufarbeitung

  1. additionAfter the addition
  2. filtrationfiltered
  3. customto separate the precipitated solids
  4. washThe solids were washed thoroughly with water
  5. customdried

Quellen und Nachweise

ORD-Eintrag
ord-62f911c33ec34c2dbe633593e1d5ee82
Quelldatensatz
uspto-grants-1998_03
Patentnummer
US05733910

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