Sodium Dithionite → 4-bromo-2,7-dimethoxy-3-hydroxy-10H-phenothiazine

HRID 231057Notes

Reaction equation

HRID 231057 reaction equation
[Br:1][C:2]1[C:3](=[O:20])[C:4]([O:18][CH3:19])=[CH:5][C:6]2[C:15]=1[S:14][C:13]1[C:8](=[CH:9][CH:10]=[C:11]([O:16][CH3:17])[CH:12]=1)[N:7]=2.[O-]S(S([O-])=O)=O.[Na+].[Na+]>C(OCC)(=O)C.O>[Br:1][C:2]1[C:15]2[S:14][C:13]3[C:8](=[CH:9][CH:10]=[C:11]([O:16][CH3:17])[CH:12]=3)[NH:7][C:6]=2[CH:5]=[C:4]([O:18][CH3:19])[C:3]=1[OH:20]

Participants

5

Reactant 2

HCID 24489Sodium DithioniteHCID 1221824-Bromo-2,7-dimethoxy-3H-phenothiazin-3-one

Product 1

HCID 138537384-bromo-2,7-dimethoxy-3-hydroxy-10H-phenothiazineYield 79.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

The compound from Step 4 (300 mg) was suspended in ethyl acetate (100 ml) and a solution of Na2S2O4 (2 g) in water (40 ml) was then added and the mixture was shaken until the orange-red coloration disappeared. The aqueous layer was decanted, the organic layer was washed with water, dried and evaporated to dryness. The resulting residue was treated with ether and filtered to afford the title compound (240 mg), m.p. 185° C.

Workup

  1. customThe aqueous layer was decanted
  2. washthe organic layer was washed with water
  3. customdried
  4. customevaporated to dryness
  5. additionThe resulting residue was treated with ether
  6. filtrationfiltered

Sources & evidence

ORD record
ord-4a252d00919a4e7fa649118b66d057e6
Source dataset
uspto-grants-1989_07
Patent number
US04845083

Reaction notes

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