methyl 4-hydroxy-2-methyl-2H-1,2-benzothiazine-3-carboxylate 1,1-dioxide → HCID 178481150, compound

HRID 1719504Notes

Reaction equation

HRID 1719504 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][C:24]([OH:27])=[CH:25][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][C:24]([OH:27])=[CH:25][CH:26]=1)=[O:17]

Participants

4

Reactant 2

HCID 54676532methyl 4-hydroxy-2-methyl-2H-1,2-benzothiazine-3-carboxylate 1,1-dioxideHCID 178507763HCID 178507763, compound

Product 1

HCID 178481150HCID 178481150, compoundYield 44.3%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

A mixture of methyl 4-hydroxy-2-methyl-2H-1,2-benzothiazine-3-carboxylate 1,1-dioxide (0.65 g) and 2-amino-5-hydroxy-2,4,6-cycloheptatrien-1-one (0.40 g) in xylene (12 ml) was refluxed for 48 hours. The reaction mixture was cooled to room temperature. The crystals were collected by filtration and washed successively with methanol, water and methanol to give 4-hydroxy-N-(5-hydroxy-1-oxo-2,4,6-cycloheptatrien-2-yl)-2-methyl-2H-1,2-benzothiazine-3-carboxamide 1,1-dioxide (0.4 g).

Workup

  1. temperaturewas refluxed for 48 hours
  2. filtrationThe crystals were collected by filtration
  3. washwashed successively with methanol, water and methanol

Sources & evidence

ORD record
ord-f934ced0852540d6ac65f00fb2c89c44
Source dataset
uspto-grants-1985_09
Patent number
US04540692

Reaction notes

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