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 1719499Notes

Reaction equation

HRID 1719499 reaction equation
[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]

Participants

4

Reactant 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

Product 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-dioxideYield 53.3%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

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.

Workup

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

Sources & evidence

ORD record
ord-692ec9fc08ed41e7982363ce4136aff3
Source dataset
uspto-grants-1985_09
Patent number
US04540692

Reaction notes

Loading…