HCID 12557655, compound → HCID 54712702, compound

HRID 1719502Notes

Reaction equation

HRID 1719502 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:29])[C:22]([O:27][CH3:28])=[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:29])[C:22]([O:27][CH3:28])=[CH:23][CH:24]=[CH:25][CH:26]=1)=[O:17]

Participants

4

Reactant 2

HCID 12557655HCID 12557655, compoundHCID 54676532methyl 4-hydroxy-2-methyl-2H-1,2-benzothiazine-3-carboxylate 1,1-dioxide

Product 1

HCID 54712702HCID 54712702, compoundYield 34.1%

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 (1.5 g) and 2-amino-7-methoxy-2,4,6-cycloheptatrien-1-one (0.8 g) in xylene (25 ml) is refluxed for 6.5 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 dimethylformamide to give 4-hydroxy-2-methyl-N-(7-methoxy-1-oxo-2,4,6-cycloheptatrien-2-yl)-2H-1,2 -benzothiazine-3-carboxamide 1,1-dioxide (0.7 g), m.p. 243°-247° C.

Workup

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

Sources & evidence

ORD record
ord-f54448515f25433e96db9b86b7a113c9
Source dataset
uspto-grants-1985_09
Patent number
US04540692

Reaction notes

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