2-Aminothiophenol → 1,5-dihydro-2H-pyrimido[4,5-b][1,4]benzothiazine-2,4(3H)-dione

HRID 36847

Reaktionsgleichung

Reaktionsgleichung von HRID 36847
O[C:2]1[C:3](=[O:9])[NH:4][C:5](=[O:8])[NH:6][CH:7]=1.BrN1C(=O)CCC1=O.[NH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[SH:25]>C(O)C>[NH:6]1[C:7]2[S:25][C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=3[NH:18][C:2]=2[C:3](=[O:9])[NH:4][C:5]1=[O:8]

Komponenten

5

Edukt 3

HCID 87132-Aminothiophenol2×HCID 67184N-bromobutanimideHCID 73268Pyrimidine-2,4,5-triol

Produkt 1

HCID 123625261,5-dihydro-2H-pyrimido[4,5-b][1,4]benzothiazine-2,4(3H)-dione

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

Then, to a solution or suspension of a 5-hydroxypyrimidine-2,4(1H,3H)-dione derivative of formula (IV) in a reaction inert solvent is added N-bromosuccinimide portion-wise at room temperature. A preferred solvent is ethanol. The reaction mixture is stirred until the derivative of formula (IV) disappears. Then, a 2-aminobenzenethiol derivative of formula (V) is added and the mixture is heated at reflux. Certain 2-aminobenzenethiol derivatives of formula (V) are commercially available and, further, the derivatives of formula (V) can be prepared from the corresponding 2-aminobenzothiazoles by hydrolysis as described by Mital, R. L., et al., J. Chem. Soc. (c), 2148 (1969). When a precipitate results after reflux of the reaction mixture, the precipitate is collected to give a 1,5-dihydro-2H-pyrimido[4,5-b][1,4]benzothiazine-2,4(3H)-dione derivative of formula (I). When no precipitate is obtained after reflux, the derivative of formula (I) is obtained by chromatographic separation on silica gel. The foregoing method for reacting derivatives of formula (IV) with derivatives of formula (V) to yield derivatives of formula (I) is analogous to the method described by Sako, M., et al., Chem. Pharm. Bull., 32, 2474 (1984).

Aufarbeitung

  1. temperaturethe mixture is heated
  2. temperatureat reflux
  3. customWhen a precipitate results
  4. temperatureafter reflux of the reaction mixture
  5. customthe precipitate is collected

Quellen und Nachweise

ORD-Eintrag
ord-2be7285113c541d18daf6ac93eeca847
Quelldatensatz
uspto-grants-1995_05
Patentnummer
US05418231

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