Quinone → Phenothiazone

HRID 979074

Reaction equation

HRID 979074 reaction equation
[C:1]1(=O)[CH:6]=[CH:5][C:4](=[O:7])[CH:3]=[CH:2]1.[NH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[SH:16]>CO>[CH:2]1[C:1]2[C:6]([S:16][C:11]3[C:10]([N:9]=2)=[CH:15][CH:14]=[CH:13][CH:12]=3)=[CH:5][C:4](=[O:7])[CH:3]=1

Participants

4

Reactant 2

HCID 4650QuinoneHCID 87132-Aminothiophenol

Product 1

HCID 68485PhenothiazoneYield 62.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a stirring suspension of 1.72 kg (16 mol) of p-benzoquinone in 13 liters MeOH at room temperature was added slowly a solution of 1.0 kg (8 mol) of 2-aminothiophenol in 600 ml MeOH over a period of 1 hour. The resulting red mixture was stirred at room temperature for another 2 hours and then the product 3H-phenothiazin-3-one was filtered off. This 3H-phenothiazin-3-one was washed thoroughly with methanol and dried to give 1.07 kg of 3H-phenothiazin-3-one (61.49% yield), m.p. 157°-159° C.

Workup

  1. filtrationthe product 3H-phenothiazin-3-one was filtered off
  2. washThis 3H-phenothiazin-3-one was washed thoroughly with methanol
  3. customdried

Sources & evidence

ORD record
ord-dde964301af245c9bdbb84ca0efff82d
Source dataset
uspto-grants-1987_05
Patent number
US04666907

Linked notes

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