Sodium Hydroxide → HCID 86740586, compound

HRID 1284457Notes

Reaction equation

HRID 1284457 reaction equation
C([O:11][C:12]1[C:17]2[S:18][CH:19]=[CH:20][C:16]=2[S:15](=[O:22])(=[O:21])[N:14]([CH3:23])[C:13]=1[C:24]([NH:26][C:27]1[C:28](=[O:34])[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1)=[O:25])(=O)C=CC1C=CC=CC=1.[OH-].[Na+]>CO>[OH:11][C:12]1[C:17]2[S:18][CH:19]=[CH:20][C:16]=2[S:15](=[O:22])(=[O:21])[N:14]([CH3:23])[C:13]=1[C:24]([NH:26][C:27]1[C:28](=[O:34])[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1)=[O:25]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 54014919HCID 54014919, compound

Product 1

HCID 86740586HCID 86740586, compoundYield 41.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a suspension of 4-cinnamoyloxy-2-methyl-N-(1-oxo-2,4,6-cycloheptatrien-2-yl)-2H-thieno[2,3-e]-1,2-thiazine-3-carboxamide 1,1-dioxide (0.49 g) in methanol (50 ml) was added dropwise 1N aqueous solution of sodium hydroxide (1.5 ml) at ambient temperature. The resultant mixture was stirred at the same temperature for 8 hours. After neutralization with 1N hydrochloric acid, the solvent was removed under reduced pressure. The residue was washed with water and dried up. The crude crystals were recrystallized from N,N-dimethyl-formamide to give 4-hydroxy-2-methyl-N-(1-oxo-2,4,6-cycloheptatrien-2-yl)-2H-thieno[2,3-e]-1,2-thiazine-3-carboxamide 1,1-dioxide (0.15 g).

Workup

  1. customAfter neutralization with 1N hydrochloric acid, the solvent was removed under reduced pressure
  2. washThe residue was washed with water
  3. customdried up
  4. customThe crude crystals were recrystallized from N,N-dimethyl-formamide

Sources & evidence

ORD record
ord-c4325d6d5b074101919df343bc4f7c62
Source dataset
uspto-grants-1986_01
Patent number
US04563453

Reaction notes

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