Acetic Acid → HCID 13853740, compound

HRID 231064Notes

Reaction equation

HRID 231064 reaction equation
C([O:4][C:5]1[C:6]([O:24][CH3:25])=[CH:7][C:8]2[NH:9][C:10]3[C:15]([S:16](=[O:21])(=[O:20])[C:17]=2[C:18]=1[Br:19])=[CH:14][C:13]([O:22][CH3:23])=[CH:12][CH:11]=3)(=O)C.[OH-].[Na+].C(O)(=O)C>CO.O>[Br:19][C:18]1[C:17]2[S:16](=[O:20])(=[O:21])[C:15]3[C:10](=[CH:11][CH:12]=[C:13]([O:22][CH3:23])[CH:14]=3)[NH:9][C:8]=2[CH:7]=[C:6]([O:24][CH3:25])[C:5]=1[OH:4]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 14798Sodium HydroxideHCID 13853741HCID 13853741, compound

Product 1

HCID 13853740HCID 13853740, compoundYield 106.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a suspension of 3-acetoxy-4-bromo-2,7-dimethoxy-10H-phenothiazine-5,5-dioxide (10.0 g) in methanol (105 ml) there was added 2N aqueous sodium hydroxide solution (74 ml) and the resulting mixture was stirred at room temperature for 20 minutes. There was then added 10% aqueous acetic acid solution (250 ml) and a thick precipitate was formed. The mixture was diluted with water (105 ml) and filtered, the solid washed with water and ether, and dried in a desiccator, affording the title compound (9.6 g). Further purification of a small sample was achieved through chromatography on a short column of silica gel, eluting with acetone. m.p.: 252°-260° (dec).

Workup

  1. customa thick precipitate was formed
  2. filtrationfiltered
  3. washthe solid washed with water and ether
  4. customdried in a desiccator

Sources & evidence

ORD record
ord-65f2a3858b984f82945d26edde02ed68
Source dataset
uspto-grants-1989_07
Patent number
US04845083

Reaction notes

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