Quinone → 2,7-Dimethyl-phenothiazone

Reaction equation

[NH2:1][C:2]1[C:7](OC)=[CH:6]C=[CH:4][C:3]=1[SH:10].[C:11]1(=[O:18])[CH:16]=[CH:15][C:14](=O)[CH:13]=[CH:12]1.CCO[C:22]([CH3:24])=O.[CH2:25](Cl)Cl>>[CH3:25][C:16]1[C:11](=[O:18])[CH:12]=[C:13]2[C:14](=[N:1][C:2]3[C:3]([S:10]2)=[CH:4][C:22]([CH3:24])=[CH:6][CH:7]=3)[CH:15]=1

Participants

Reactant 4

HCID 4650Quinone

HCID 6344Dichloromethane

HCID 8857Ethyl Acetate

HCID 126318592-Amino-3-methoxybenzene-1-thiol

Product 1

HCID 3693912,7-Dimethyl-phenothiazone

Procedure

Following the procedure described in Example 10 but substituting 2-amino-5-methylthiophenol for 2-amino-3-methoxythiophenol and substituting 2-methyl-p-benzoquinone for p-benzoquinone, a mixture of the title compounds were obtained. Chromatography on silica gel eluting with 10% EtOAc in CH2Cl2 afforded firstly 2,7-dimethyl-3H-phenothiazin-3-one, m.p. 177° C.