Benzenamine, 3-(methylthio)- → HCID 70578334, compound

HRID 1155530Notes

Reaction equation

HRID 1155530 reaction equation
[CH3:1][S:2]C1C=C(C=CC=1)N.[CH3:10][S:11][C:12]1[CH:13]=[C:14]([CH:23]=[CH:24][CH:25]=1)[NH:15][CH:16]=[C:17](C)[C:18]([O:20]C)=S.C([O-])(=O)C=C>>[CH3:1][S:2][CH:17]1[C:18](=[O:20])[C:23]2[C:14](=[CH:13][C:12]([S:11][CH3:10])=[CH:25][CH:24]=2)[N:15]=[CH:16]1

Participants

4

Reactant 3

HCID 15693Benzenamine, 3-(methylthio)-HCID 25188AcrylateHCID 86738122HCID 86738122, compound

Product 1

HCID 70578334HCID 70578334, compound

Procedure

Using the methods described in Example 11 and Example 12, 3-methylthioaniline was converted to methyl 3-(3-methylthioanilino)-2-methylthioacrylate, m.p. 90°-92°. This acrylate was cyclised to give 3,7-bis(methylthio)4-quinolone, m.p. 197°-200°, containing the corresponding 5-methylthio isomer. This product was methylated with dimethyl sulphate in aqueous potassium hydroxide at room temperature to give a mixture of 1-methyl-3,7-bis (methylthio)-4-quinolone and 1-methyl-3,5-bis(methylthio)-4-quinolone. This mixture was separated by high pressure liquid chromatography to give 1-methyl-3,7-bis(methylthio)-4-quinolone, m.p. 154°-155° (from ethanol). Oxidation of this compound with 3-chloroper benzoic acid gave 1-methyl-3-methylsulphinyl-7-methylthio-4-quinolone, m.p. 196°-198° (from ethanol).

Sources & evidence

ORD record
ord-6f813fc64a7a4e2b8ab020acbb4d15a2
Source dataset
uspto-grants-1981_11
Patent number
US04302460

Reaction notes

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