Methyl Isothiourea Sulfate

Methylene bis(guanidinomethane), CH2(-CHa.NH.C( NH).NH2)2 mw 158.21, N 53.16% hygr crysts, mp 135° sol in ale 8t w. Prepd by creating methylene bis(aminomethane) with s-methyl isothiourea sulfate. More recently isolated as the dipicrote salt by heating a mixt of cyanamide, methylene bis(aminomethane), and methylene bis (aminomethane p-toluene-sulfcnate), then treating with PA for the dipicrate mw 616.42, N 27.27%, OB —77.9%, mp 242°. Their expl props were not investigated... 

Methyl ami noguanidine, (CH3)NH-NH C(NHa) NH or (CHj)HN-N C(NHa )a, was prepd as the sulfate by heating on a water bath coned solns of methylhydrazine and S-methyl-isothiourea sulfate. It was patented in Germany... 

Szab6, C., Southan, G. J., and Thiemermann, C. (1994e). Beneficial effects and improved survival in rodent models of septic shock with S-methyl-isothiourea sulfate, a novel, potent and selective inhibitor of inducible nitric oxide synthase. Proc. Natl. Acad. Sci. U.S.A. 91, 12472-12476. 

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. 

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

The alkyl esters of N-benzimidazol-2-yl-carbamic acid (22) can be prepared by the methylation of thiourea with dimethyl sulfate and the subsequent N-acylation in alkaline medium of the S-methyl-isothiourea formed (23) with the alkyl ester of chloroformic acid. Finally, N,N -bis(alkoxycarbonyl)-S-methylthiourea (24), obtained as an intermediate product is condensed with o-phenylene diamine in glacial acetic acid. 

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... 

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