Hydrochloric Acid → HCID 54712695, compound

HRID 1719509Notes

Reaction equation

HRID 1719509 reaction equation
[O:1]=[C:2]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=[C:3]1[NH:9][C:10]([C:12]1[N:13]([CH3:35])[S:14](=[O:34])(=[O:33])[C:15]2[CH:32]=[CH:31][CH:30]=[CH:29][C:16]=2[C:17]=1[O:18]C(=O)C=CC1C=CC=CC=1)=[O:11].[OH-].[Na+].Cl>CO>[OH:18][C:17]1[C:16]2[CH:29]=[CH:30][CH:31]=[CH:32][C:15]=2[S:14](=[O:33])(=[O:34])[N:13]([CH3:35])[C:12]=1[C:10]([NH:9][C:3]1[C:2](=[O:1])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1)=[O:11]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 54091092HCID 54091092, compound

Product 1

HCID 54712695HCID 54712695, compoundYield 27.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a suspension of N-(1-oxo-2,4,6-cycloheptatrien-2-yl)-2-methyl-4-cinnamoyloxy-2H-1,2-benzothiazine-3-carboxamide 1,1-dioxide (0.5 g) in methanol (50 ml) was added dropwise 1N sodium hydroxide solution (1.5 ml) at room temperature. The mixture was stirred for 8 hours at room temperature and then neutralized with 1N hydrochloric acid. The mixture was evaporated under reduced pressure and the residue was washed with water and dried to give crystals, which were recrystallized from N,N-dimethylformamide to give 4-hydroxy-2-methyl-N-(1-oxo-2,4,6-cycloheptatrien-2-yl)-2H-1,2-benzothiazine-3-carboxamide 1,1-dioxide (0.1 g).

Workup

  1. customThe mixture was evaporated under reduced pressure
  2. washthe residue was washed with water
  3. customdried
  4. customto give crystals, which
  5. customwere recrystallized from N,N-dimethylformamide

Sources & evidence

ORD record
ord-5883307a251d4775beb39a2481d8c943
Source dataset
uspto-grants-1985_09
Patent number
US04540692

Reaction notes

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