Thiazolyl guanidines

C7H15CI2N3S 38603-72-4) see Cimetidine [4-[[(2-aminoethyl)thio]methyI]-2-thiazolyl]guanidine (C7H iN,S2 71916-66-0) see Ebrotidine... 

CijHjdCINOjS 123435-16-5) see Mosapramine [4-(chloromcthyl)-2-thiazolyl]guanidine (C5H7CIN4S 81152-53-6) see Ebrotidine A -(2-chloro-4-methyl-3-thienyl)thiourea (CHH7CIN2S2) see Tiamenidine... 

C15H14N4OS3 76823-90-0) see Famotidine [4-[[(2-cyanoethyl)thio]methylJ-2-thiazolyl]guanidine (CjHiiNjSj 76823-93-3) see Famotidine 9-cyanofluorene... 

AT-Phcnyl-AT,-(2-thiazolyl)guanidine forms 2 1 complexes with Cu11 and Hg11 and 1 1 complexes with WV1 and Movl as indicated by absorption spectra, conductometric and amperometric measurements.171 Room temperature Mossbauer parameters have been tabulated for dehydro-A, A, A"-trialkylguanidinohexacarbonyldiiron(O) and related compounds.172... 

The 111.6 kg resultant precipitates of N"-[4-(chloromethyl)-4,5-dihydro-4-hydroxy-2-thiazolyl]-guanidine hydrochloride are collected, and washed with 50 L of acetone. In 500 ml of water are dissolved 111.6 kg of N"-[4-(chloromethyl)-4,5-dihydro-4-hydroxy-2-thiazolyl]-guanidine hydrochloride and 32.9 kg of thiourea. The solution is stirred for one hour at 50°C. N -[4-[[(Aminoiminomethyl)thio]methyl]-2-thiazolyl]-guanidine dihydrochloride is formed in the reaction mixture, and this reaction mixture containing this compound is directly used for the next process without isolation of the formed compound. 

The reaction mixture obtained is cooled below 10°C, and to the solution are added 45.6 kg of beta-chloropropionitrile and 200 L of isopropanol. A solution of 69.1 kg of sodium hydroxide in 280 L of water is added dropwise to the solution under nitrogen stream followed by stirring for 2 hours at 0°C. The crystals precipitated are collected by filtration, and washed with cold water and dried to provide 91.7 kg of the N"-[4-[[(2-cyanoethyl)thio]methyl]-2-thiazolyl]-guanidine, melting point 125-126.5°C. 

In 60 L of anhydrous dimethylformamide is dissolved 34.3 kg of the N"-[4-[[(2-cyanoethyl)thio]methyl]-2-thiazolyl]-guanidine. After adding 60 L of anhydrous methanol to the solution, 61.9 kg of hydrogen chloride gas is passed through the solution below 5°C. After stirring the reaction mixture for 2 days at 0°C, the reaction mixture is poured into a mixture of 350 L of water, 250 kg of potassium carbonate, 30 L of ethyl acetate and ice while stirring below 5°C for 2 hours. The resultant precipitates are collected by filtration. After stirring a mixture of the precipitates and 400 L of water for 0.5 hour at 0°, the resultant precipitates are collected by filtration, washed with 40 L of water and 10 L of cooled acetone respectively, and dried at reduced pressure... 

N-(2-Thiazolyl)cyanamide may be converted into guanidino derivatives by the action of hydrazines (487). N-Aryl-N -(4-aryl-2-thiazolyl)guanidines... 

The scope of this mechanism for the reaction of a series of nucleophiles with hydroperoxides has been reviewed and a linear free-energy plot of ogkz against logArj derived for acid-catalysed oxidations. The reaction of l-aIkyl-3-aryl-thioureas with HgOa yields 1,2,4-thiadiazoles which rearrange in acidic solutions to thiazolyl-guanidines. The formation of amidinothioureas as precursors of the thiadiazoles has, however, been established. 

When desulfurized with Pb02, l-aryI 3-(4-p-tolyl-2-thiazolyl)thioureas yield the heterocyclic guanidines (262) (Scheme 159) (299, 496, 497). 

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