Methyl isothiourea, reaction of sulfate

MethylindOle, 22, 94 Methyl isothiocyanate, 21, 81, 83 Methyl isothiourea, reaction of sulfate... 

Methylindole, 22, 94 Methyl isothiocyanate, 21, 81, 83 Methyl isothiourea, reaction of sulfate with hydrazine sulfate, 26, 9 Methyl lactate, 26, 6 6-Methyllepidine, 26, 47 8-MethyUepidine, 26, 47 a-Methyl-d-mannoside, 22, 86 Methyl mercaptan, 26, 9 N-Methyl- (3 methoxy-4-hydroxy-phenyl)-alanine, 22, 91 2-Methyl-6-methoxyqumohne, 26, 47 Methyl myristate, 20, 67 a-Methylnaphthalene, 26, 93 Methyb -octylamine, 25, 19 Methyl palmitate, 20, 67 Methylphenyldiketoke, 23,1 /3-(2-MEIH LPHENYL)-JiTUYLAMlNE, 23, 72... 

The process starts from a Knovengol condensation of ethyl isobutyryl acetate with 4-fluorobenzaldehyde. The reaction of S -methyl isothiourea sulfate with a,P-unsaturated ketone followed by oxidation with DDQ gives 2-(methylthio)pyrimidine. This intermediate was further oxidized by w-CPBA to yield 2-(methylsulfonyl)pyrimidine. Aromatic substitution with methyl amine and sulfonylation afford methanesulfonamide derivative. The required alcohol can be synthesized by DIBAL reduction of the corresponding ester as... 

Prepared from /7-hydrorQrmetbyl sulfide and thionyl ddmide (403) essentially by the method of Kimer (462). j9-hydroxymethyl sulfide is prepared from methyl isothiourea sulfate through methyl mercaptan and sodium methyl sulfide and reaction of the latter with ethylene ehlorohydtin by the method of Windus and Shildneck (868). Methyl mercaptan is available commercially. 

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