5-Amino-2-hydroxy-2,4,6-cycloheptatrien-1-one → 4-hydroxy-2-methyl-N-(2-hydroxy-1-oxo-2,4,6-cycloheptatrien-5-yl)-2H-1,2-benzothiazine-3-carboxamide 1,1-dioxide

HRID 1719499

Reaktionsgleichung

Reaktionsgleichung von HRID 1719499
[OH:1][C:2]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[S:5](=[O:13])(=[O:12])[N:4]([CH3:14])[C:3]=1[C:15]([O:17]C)=O.[NH2:19][C:20]1[CH:26]=[CH:25][C:24](=[O:27])[C:23]([OH:28])=[CH:22][CH:21]=1>C1(C)C(C)=CC=CC=1>[OH:1][C:2]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[S:5](=[O:12])(=[O:13])[N:4]([CH3:14])[C:3]=1[C:15]([NH:19][C:20]1[CH:26]=[CH:25][C:24](=[O:27])[C:23]([OH:28])=[CH:22][CH:21]=1)=[O:17]

Komponenten

4

Edukt 2

HCID 234505-Amino-2-hydroxy-2,4,6-cycloheptatrien-1-oneHCID 54676532methyl 4-hydroxy-2-methyl-2H-1,2-benzothiazine-3-carboxylate 1,1-dioxide

Produkt 1

HCID 547126974-hydroxy-2-methyl-N-(2-hydroxy-1-oxo-2,4,6-cycloheptatrien-5-yl)-2H-1,2-benzothiazine-3-carboxamide 1,1-dioxideAusbeute 53,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 7237O-XyleneLösungsmittel

Versuchsvorschrift

In a nitrogen atmosphere, a solution of methyl 4-hydroxy-2-methyl-2H-1,2-benzothiazine-3-carboxylate 1,1-dioxide (0.54 g) and 5-amino-2-hydroxy-2,4,6 -cycloheptatrien-1-one (0.33 g) in xylene (15 ml) is refluxed for 7.5 hours. The reaction mixture is then allowed to stand at room temperature overnight. The crystals that have separated out are collected by filtration and recrystallized from dimethylformamidemethanol to give 4-hydroxy-2-methyl-N-(2-hydroxy-1-oxo-2,4,6-cycloheptatrien-5-yl)-2H-1,2-benzothiazine-3-carboxamide 1,1-dioxide (0.4 g), m.p. 258°-265° C.

Aufarbeitung

  1. customThe crystals that have separated out
  2. filtrationare collected by filtration
  3. customrecrystallized from dimethylformamidemethanol

Quellen und Nachweise

ORD-Eintrag
ord-692ec9fc08ed41e7982363ce4136aff3
Quelldatensatz
uspto-grants-1985_09
Patentnummer
US04540692

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