Synthesis of α-Mercaptoacetamidinium Chlorides via the Corresponding Phosphorothioates

Conway, T. T.; Shoeb, A.; Bauer, Ludwig

doi:10.1002/jps.2600570318

Cited by 6 publications

(1 citation statement)

References 9 publications

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“…This latter substance has often been used to prepare aliphatic thiols from the corresponding halo alkanes (see ref. 8 for e~a m p l e ) ,~ but to our knowledge it has not heretofore been utilized for the synthesis of heterocyclic thiones. The parent member of this series was obtained from the known (9) disulfide 4 (Scheme 2) in a manner identical to that described by Soderback (10) for the preparation of the 5-chloro analog.…”

Section: -Substitutedmentioning

confidence: 99%

Five-membered Heterocyclic Thiones. Part IV. 1,2,4-Thiadiazole-3-thiolates and 1,2,4-Thiadiazole-5-thione

Lacasse¹,

Muchowski²

1973

Can. J. Chem.

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1,2,4-Thiadiazole-Sthione (2a) was synthesized from the corresponding 5-bromo compound. An alternative synthesis of the known 3-methyl-l,2,4-thiadiazole-5-thione is described. It was shown by i.r. spectroscopy that the parent compound and its 3-methyl derivative existed in the thione form in the solid state.Mercuric-l,2,4-thiadiazole-3-thiolate (5) was prepared by cleavage of the corresponding disulfide with mercury. The mercuric salt was converted to a stable (in solution) sodium salt, but the free thio compound was not isolable.Le thiadiazole-1,2,4 thione-5 (2a) a CtC synthCtisC B partir du composC correspondant bromo-5. On dtcrit une nouvelle synthkse du compose connu suivant, le mCthyl-3 thiadiazole-1,2,4 thione-5. I1 a CtC montrk B I'aide de la spectroscopie i.r. que le composC parent et son dCrivC methyl-3 existe h I'Ctat solide sous la forme thione.Le thiolate-3 mercurique de thiadiazole-1,2,4 (5) a CtC prepark par clivage B I'aide du mercure du disulfure correspondant. Le sel mercurique a CtC converti en un sel de sodium stable (en solution) mais le compose thio libre n'a pu Ctre isolC.[Traduit par le journal]Can. J. Chern., 51, 2353 (1973) There are two possible 1,2,4-thiadiazole thiols, and ring-substituted representatives of each isomer are known (2,3), but the parent members have not, to our knowledge, been previously described. 3-

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Section: -Substitutedmentioning

confidence: 99%

Five-membered Heterocyclic Thiones. Part IV. 1,2,4-Thiadiazole-3-thiolates and 1,2,4-Thiadiazole-5-thione

Lacasse¹,

Muchowski²

1973

Can. J. Chem.

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Synthesis of 2‐amino‐4‐imino‐4,5‐dihydrothiazoles from N‐sulfonyl‐α‐chloroamidines and thiourea

Abdelaal

Bauer

1988

Journal of Heterocyclic Chem

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A number of new and interesting 2‐amino‐4‐(N‐substituted)imino‐4,5‐dihydrothiazoles were synthesized by reacting thiourea (or thiourea hydrochloride) with N‐alkyl‐ or N,N‐dialkyl‐N′‐p‐toluenesulfonyl‐α‐chloroacetamidines, where the N,N‐alkyl groups were ethyl, cyclohexyl, benzyl, β‐phenethyl, (3,5‐dimethyl‐1‐adamantyl)‐methyl, as well as N,N‐dimethyl‐ and N,N‐pentamethylene. Reactions of N‐alkyl‐N‐p‐toluenesulfonyl‐2‐chloroacetamidines (substituents being N‐ethyl, N‐benzyl and N,N‐dimethyl) with thiourea hydrochloride in hot 2‐propanol furnished 2‐amino‐4‐(p‐toluenesulfonyl)imino‐4,5‐dihydrothiazole (in 51, 60 and 65% yields, respectively) and the corresponding amine hydrochloride. In hot acetone or butanone, the reactions of these N‐sulfonyl‐2‐chloroacetamidines with excess thiourea provided 2‐amino‐4‐N‐(alkyl or N,N‐dialkyl)imminium‐4,5‐dihydrothiazole chlorides in 25–80% yield. The by‐product from these reactions was p‐toluenesulfonamide. The structures of the products were established by chemical transformations and spectral methods (nmr and mass spectra).

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Regioselective preparation of functional aryl ethers and esters by stepwise nucleophilic aromatic substitution reaction

Parthiban

2014

Journal of Fluorine Chemistry

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Synthesis of α-Mercaptoacetamidinium Chlorides via the Corresponding Phosphorothioates

Cited by 6 publications

References 9 publications

Five-membered Heterocyclic Thiones. Part IV. 1,2,4-Thiadiazole-3-thiolates and 1,2,4-Thiadiazole-5-thione

Five-membered Heterocyclic Thiones. Part IV. 1,2,4-Thiadiazole-3-thiolates and 1,2,4-Thiadiazole-5-thione

Synthesis of 2‐amino‐4‐imino‐4,5‐dihydrothiazoles from N‐sulfonyl‐α‐chloroamidines and thiourea

Regioselective preparation of functional aryl ethers and esters by stepwise nucleophilic aromatic substitution reaction

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