Dimethylformamide → 2,7-dimethoxy-3H-phenothiazin-3-one

HRID 979296Notes

Reaction equation

HRID 979296 reaction equation
[CH3:1][O:2][C:3]1[C:4](=[O:10])[CH:5]=[CH:6][C:7](=O)[CH:8]=1.[NH2:11][C:12]1[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][C:13]=1[SH:20].CN(C=O)C>CO>[CH3:1][O:2][C:3]1[C:4](=[O:10])[CH:5]=[C:6]2[C:7](=[N:11][C:12]3[C:13]([S:20]2)=[CH:14][C:15]([O:18][CH3:19])=[CH:16][CH:17]=3)[CH:8]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 761462-Methoxy-1,4-benzoquinoneHCID 2355092-Amino-5-methoxybenzene-1-thiol

Product 1

HCID 121999232,7-dimethoxy-3H-phenothiazin-3-one

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a suspension of 2-methoxy-p-benzoquinone, (1.15 kg) (Step 1) in methanol (8 l) was added portionwise a suspension of 2-amino-5-methoxythiophenol (from Step 2) in methanol (6 l). The reaction mixture was stirred for 15 minutes at room temperature, filtered and the collected solid washed with methanol (8 l). The product isolated was swished with DMF (16 l) for 2 hours, filtered and air-dried. The crude material was dissolved in hot DMF (16 l) (130°-140° C.), filtered through Celite and the filtrate cooled to room temperature. The crystals were filtered, washed with methanol (8 l) and air-dried to afford the title compound (703 g), m.p. 237°-238° C.

Workup

  1. additionwas added portionwise
  2. filtrationfiltered
  3. washthe collected solid washed with methanol (8 l)
  4. customThe product isolated
  5. filtrationfiltered
  6. customair-dried
  7. dissolutionThe crude material was dissolved in hot DMF (16 l) (130°-140° C.)
  8. filtrationfiltered through Celite
  9. temperaturethe filtrate cooled to room temperature
  10. filtrationThe crystals were filtered
  11. washwashed with methanol (8 l)
  12. customair-dried

Sources & evidence

ORD record
ord-a838e8a04f2a42f7b13ed024892e1e6a
Source dataset
uspto-grants-1987_05
Patent number
US04667032

Reaction notes

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