methyl 4-hydroxy-2-methyl-2H-1,2-benzothiazine-3-carboxylate 1,1-dioxide → HCID 178481148, compound

HRID 1719506Notes

Reaction equation

HRID 1719506 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])[C:22]([OH:27])=[CH:23][CH:24]=[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])[C:22]([OH:27])=[CH:23][CH:24]=[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 178507571HCID 178507571, compound

Product 1

HCID 178481148HCID 178481148, compoundYield 90.4%

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 (2.95 g) and 2-amino-7-hydroxy-2,4,6-cycloheptatrien-1-one (1.5 g) in xylene (103 ml) was refluxed for 52 hours. The reaction mixture was cooled to room temperature. The crystals were collected by filtration and washed successively with N,N-dimethylformamide and chloroform to give 4-hydroxy-N-(7-hydroxy-1-oxo-2,4,6-cycloheptatrien-2-yl)-2-methyl-2H-1,2-benzothiazine-3-carboxamide 1,1-dioxide (3.7 g).

Workup

  1. temperaturewas refluxed for 52 hours
  2. filtrationThe crystals were collected by filtration
  3. washwashed successively with N,N-dimethylformamide and chloroform

Sources & evidence

ORD record
ord-f88f88313e9d4841aeb4886ac77e1894
Source dataset
uspto-grants-1985_09
Patent number
US04540692

Reaction notes

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