HCID 12557673, compound → HCID 54712699, compound

HRID 1719505Notes

Reaction equation

HRID 1719505 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]([Cl:27])=[CH:25][CH:26]=1>C1(C)C(C)=CC=CC=1>[Cl:27][C:24]1[CH:23]=[CH:22][C:21](=[O:28])[C:20]([NH:19][C:15]([C:3]2[N:4]([CH3:14])[S:5](=[O:12])(=[O:13])[C:6]3[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=3[C:2]=2[OH:1])=[O:17])=[CH:26][CH:25]=1

Participants

4

Reactant 2

HCID 12557673HCID 12557673, compoundHCID 54676532methyl 4-hydroxy-2-methyl-2H-1,2-benzothiazine-3-carboxylate 1,1-dioxide

Product 1

HCID 54712699HCID 54712699, compoundYield 40.7%

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 (1.5 g) and 2-amino-5-chloro-2,4,6-cycloheptatrien-1-one (0.87 g) in xylene (37 ml) was refluxed for 24 hours. The reaction mixture was cooled to room temperature. The crystals were collected by filtration and recrystallized from N,N-dimethylformamide to give N-(5-chloro-1-oxo-2,4,6-cycloheptatrien-2-yl)-4-hydroxy-2-methyl-2H-1,2-benzothiazine-3-carboxamide 1,1-dioxide (0.89 g).

Workup

  1. temperaturewas refluxed for 24 hours
  2. filtrationThe crystals were collected by filtration
  3. customrecrystallized from N,N-dimethylformamide

Sources & evidence

ORD record
ord-a83a937ca36c4318a448c7744e506a25
Source dataset
uspto-grants-1985_09
Patent number
US04540692

Reaction notes

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