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

HRID 231055

Reaction equation

HRID 231055 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-1e5ec47aeb7d4438b19702d3e772f9dc
Source dataset
uspto-grants-1989_07
Patent number
US04845083

Linked notes

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