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

HRID 979089Notes

Reaction equation

HRID 979089 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 reacting mixture was stirred for 15 minutes, filtered and 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 on Celite and the filtrate cooled to room temperature. The resulting crystals were filtered, washed with methanol (8 l) and air-dried to afford the title compound (70.3 g), m.p. 237°-238° C.

Workup

  1. additionwas added portionwise
  2. filtrationfiltered
  3. washwashed 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 on Celite
  9. filtrationThe resulting crystals were filtered
  10. washwashed with methanol (8 l)
  11. customair-dried

Sources & evidence

ORD record
ord-a4d4737fd03642259e481e42759a0931
Source dataset
uspto-grants-1987_05
Patent number
US04666907

Reaction notes

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