Acetic Acid → 5-Hydroxy-12H-benzo[a]phenothiazine-7,7-dioxide

HRID 64975Notes

Reaction equation

HRID 64975 reaction equation
C([O:4][C:5]1[CH:18]=[C:17]2[C:8]([NH:9][C:10]3[C:15]([S:16]2(=[O:20])=[O:19])=[CH:14][CH:13]=[CH:12][CH:11]=3)=[C:7]2[CH:21]=[CH:22][CH:23]=[CH:24][C:6]=12)(=O)C.[OH-].[Na+].C(O)(=O)C>CO>[OH:4][C:5]1[CH:18]=[C:17]2[C:8]([NH:9][C:10]3[C:15]([S:16]2(=[O:20])=[O:19])=[CH:14][CH:13]=[CH:12][CH:11]=3)=[C:7]2[CH:21]=[CH:22][CH:23]=[CH:24][C:6]=12

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 14798Sodium HydroxideHCID 13712482HCID 13712482, compound

Product 1

HCID 137124805-Hydroxy-12H-benzo[a]phenothiazine-7,7-dioxide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a suspension of 5-acetoxy-12H-benzo[a]phenothiazine-7,7-dioxide (6.6 g) in methanol (200 ml) there was added 2N aqueous sodium hydroxide solution (132 ml) and the mixture was stirred in the absence of air at room temperature for 7 minutes; at that point an amber solution had resulted. There was rapidly added 10% aqueous acetic acid solution (200 ml) causing precipitation of the title compound which was collected by filtration (5.68 g). A sample (500 mg) was crystallized from THF affording purified product (250 mg), m.p. 334° C. (dec).

Workup

  1. customat that point an amber solution had resulted
  2. customprecipitation of the title compound which
  3. filtrationwas collected by filtration (5.68 g)
  4. customA sample (500 mg) was crystallized from THF affording
  5. custompurified product (250 mg), m.p. 334° C. (dec)

Sources & evidence

ORD record
ord-b429bbb0851841aea065bd023f2c4c9d
Source dataset
uspto-grants-1986_09
Patent number
US04611056

Reaction notes

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