Oxygen → 2H-Pyrimido[4,5-b][1,4]benzothiazine-2,4(3H)-dione

HRID 36848

Reaktionsgleichung

Reaktionsgleichung von HRID 36848
[NH:1]1[C:6]2[S:7][C:8]3[CH:14]=[CH:13][CH:12]=[CH:11][C:9]=3[NH:10][C:5]=2[C:4](=[O:15])[NH:3][C:2]1=[O:16].[H][H].CCOC(/N=N/C(OCC)=O)=O.C1(=O)C=CC(=O)C=C1.ClC1C(=O)C(C#N)=C(C#N)C(=O)C=1Cl.O=O>C(#N)C>[N:1]1[C:2](=[O:16])[NH:3][C:4](=[O:15])[C:5]2[C:6]=1[S:7][C:8]1[CH:14]=[CH:13][CH:12]=[CH:11][C:9]=1[N:10]=2

Komponenten

8

Edukt 6

HCID 977OxygenHCID 4650QuinoneHCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 5462977Diethyl azodicarboxylate2×HCID 123625261,5-dihydro-2H-pyrimido[4,5-b][1,4]benzothiazine-2,4(3H)-dioneHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 135843152H-Pyrimido[4,5-b][1,4]benzothiazine-2,4(3H)-dione

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

When derivative compounds of formula (II) are desired, a solution or suspension of 1,5-dihydro-2H-pyrimido[4,5-b][1,4]benzothiazine-2,4(3H)-dione derivative of formula (I) wherein R4 is hydrogen in acetonitrile is prepared. To that solution or suspension at room temperature is added, dropwise, an oxidant such as diethylazodicarboxylate, 1,4-benzoquinone or 2,3-dichloro-5,6-dicyano-1,4-benzoquinone. Alternatively, oxygen can be used as the oxidant. A preferred oxidant is diethylazodicarboxylate. The reaction mixture is stirred. When a precipitate results, the precipitate is collected an washed with diethylether to give a 2H-pyrimido[4,5-b][1,4]benzothiazine-2,4(3H)-dione derivative of formula (II). When no precipitate is obtained after oxidation, the solvent is removed from the reaction mixture, and the residue is triturated with diethylether and filtered to give a compound of formula (II).

Aufarbeitung

  1. customis prepared
  2. additionTo that solution or suspension at room temperature is added
  3. customWhen a precipitate results
  4. customthe precipitate is collected
  5. washan washed with diethylether

Quellen und Nachweise

ORD-Eintrag
ord-55b65922f3b64bb19f3ef7abffd4a7bc
Quelldatensatz
uspto-grants-1995_05
Patentnummer
US05418231

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