HCID 12538206, compound → HCID 54712701, compound

HRID 1719500Notes

Reaction equation

HRID 1719500 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[C:21](=[O:28])[CH:22]=[CH:23][CH:24]=[C:25]([CH3:27])[CH:26]=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[C:21](=[O:28])[CH:22]=[CH:23][CH:24]=[C:25]([CH3:27])[CH:26]=1)=[O:17]

Participants

4

Reactant 2

HCID 12538206HCID 12538206, compoundHCID 54676532methyl 4-hydroxy-2-methyl-2H-1,2-benzothiazine-3-carboxylate 1,1-dioxide

Product 1

HCID 54712701HCID 54712701, compoundYield 24.1%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

A solution of methyl 4-hydroxy-2-methyl-2H-1,2-benzothiazine-3-carboxylate 1,1-dioxide (2.4 g) and 2-amino-4-methyl-2,4,6-cycloheptatrien-1-one (1.3 g) in xylene (50 ml) is refluxed for 7 hours. The reaction mixture is then allowed to stand at room temperature overnight. The resulting crystals (1.0 g) are collected by filtration and recrystallized from dioxane to give 4-hydroxy-2-methyl-N-(4-methyl-1-oxo-2,4,6-cycloheptatrien-2-yl)-2H-1,2-benzothiazine-3-carboxamide 1,1-dioxide (0.8 g), m.p. 235°-242° C.

Workup

  1. filtrationThe resulting crystals (1.0 g) are collected by filtration
  2. customrecrystallized from dioxane

Sources & evidence

ORD record
ord-1cc03cd0d9704892b4035548d4d9d5b9
Source dataset
uspto-grants-1985_09
Patent number
US04540692

Reaction notes

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