text: in the general formulae described above , the alkyl group of 1 to 3 carbon atoms includes a methyl group , an ethyl group , a propyl group , and an isopropyl group and the acid addition salts of the compounds shown by general formulae ( i ), ( ii ) and ( iii 2 ) include mineral acid salts such as hydrochlorides , sulfates , etc ., of these compounds . the reaction of the compound of the general formula ( ii ) or an acid addition salt thereof and the cyanamide derivative shown by the formula ( iii 1 ) is performed by reacting both compounds in a proper organic solvent under heating . in this case , when the cyanamide derivative shown by the general formula ( iii 1 ) is used in an excessive amount to the amount of the compound ( ii ) or an acid addition salt , a good result is obtained . a suitable solvent which is used for the reaction includes methanol , ethanol , n - buthanol , iso - propanol , methylcellosolve and the like . the reaction is usually performed at about the reflux temperature of the solvent used but can be performed at temperatures higher than or lower than the aforesaid temperature . the reaction is accelerated by the addition of a catalyst . as the catalyst , a lewis acid is suitable for example , zinc oxide , zinc chloride , copper [ i ] chloride , aluminum chloride and the like , can be used . the product is isolated from the reaction mixture and purified by extraction using an organic solvent , crystallization , or , if necessary , column chromatography . then , the reaction of the compound of formula ( ii ) or an acid addition salt thereof and the amidinopyrazole derivative shown by the formula ( iii 2 ) is performed by directly heating these compound without using solvent or heating these compounds in a highboiling solvent . as the high - boiling solvent , for example , 1 , 3 - dimethyl - 2 - imidazolidinone and the like , can be used . as the amidinopyrazole derivative shown by the formula ( iii 2 ), there are amidinopyrazoles substituted by an alkyl group having 1 to 3 carbon atoms at the pyrazole ring , such as 3 - methylamidinopyrazole , 3 , 5 - dimethylamidinopyrazole and the like , in addition to amidinopyrazole . the amidinopyrazole derivative of formula ( iii 2 ) can be supplied to the reaction as an acid addition salt thereof such as a hydrochloride and the like . in addition , the production process of the amidinopyrazole derivative of formula ( iii 2 ) or the acid addition salt thereof is reported in &# 34 ; journal of the american chemical society &# 34 ;, vol . 75 , 4053 ( 1953 ). the amount of the amidinopyrazole of formula ( iii 2 ) is employed in excess . the amount thereof is usually at least twice the molar amount of the compound shown by formula ( ii ). the reaction is properly performed at 100 ° c . or temperatures higher than 100 ° c . the product can be easily isolated by extraction using an organic solvent or recrystallization . then , the invention will further be explained more practically by the following examples . example 1 ## str8 ## to 6 . 8 g of 3 -( 2 - aminothiazol - 4 - ylmethylthio )- propionitrile was added 80 ml of isopropanol and while stirring the mixture , 1 . 3 g of hydrogen chloride gas was introduced into the mixture . then , after adding thereto 0 . 8 g of zinc oxide and 8 g of cyanamide , the mixture was refluxed for 24 hours . furthermore , the operation of adding 8 g of cyanamide to the mixture followed by refluxing for 24 hours was repeated twice . after cooling , 150 ml of methanol was added to the reaction mixture thus obtained , insoluble matters were filtered away , and the filtrate then formed was evaporated under reduced pressure . to the residue formed were added 35 ml of methanol and 180 ml of water , and then after further adding thereto 5 g of anhydrous potassium carbonate with stirring , the product was extracted using a mixture of chloroform and methanol ( 4 : 1 ). the organic layers formed were collected , concentrated under reduced pressure , and the residue thus formed was separated using silica gel column chromatography and concentrated . the residue thus formed was crystallized in a mixture of water and isopropanol and recovered by filtration to provide 3 . 8 g of 3 -( 2 - guanidinothiazol - 4 - ylmethylthio ) propionitrile having a melting point of 129 ° to 130 ° c . by following almost the same procedure as in example 1 using the solvents and catalysts as shown in the following table , the same compound as example 1 was obtained . ______________________________________ reaction amount ofexample solvent catalyst cyanamide______________________________________2 isopropanol znf . sub . 2 ( cata - 16 mole times lytic amount ) 3 &# 34 ; zncl . sub . 2 ( cata - &# 34 ; lytic amount ) 4 &# 34 ; zni . sub . 2 ( cata - &# 34 ; lytic amount ) 5 &# 34 ; zno ( cata - &# 34 ; lytic amount ) 6 methanol zncl . sub . 2 ( 0 . 3 mole ) &# 34 ; 7 ethanol zncl . sub . 2 ( 0 . 3 mole ) &# 34 ; 8 n - butanol zncl . sub . 2 ( 0 . 3 mole ) &# 34 ; 9 methylcello - zncl . sub . 2 ( 0 . 3 mole ) &# 34 ; solve10 methanol zno ( 0 . 3 mole ) &# 34 ; 11 ethanol zno ( 0 . 3 mole ) &# 34 ; 12 n - butanol zno ( 0 . 3 mole ) &# 34 ; 13 methylcello - zno ( 0 . 3 mole ) &# 34 ; solve______________________________________ to 5 g of 3 -( 2 - aminothiazol - 4 - ylmethylthio ) propionitrile were added 11 g of amidinopyrazole hydrochloride and 15 ml of 1 , 3 - dimethyl - 2 - imidazolidinone and the mixture was heated to 110 °- 120 ° c . for 4 hours . after cooling , 120 ml of water was added to the reaction mixture and then the product was extracted twice with 50 ml of ethyl acetate and washed . the aqueous layer thus formed was collected , added with 11 g of anhydrous potassium carbonate and 10 ml of isopropanol , the crystals thus formed were collected by filtration to provide 2 . 33 g of 3 -( 2 - guanidinothiazol - 4 - ylmethylthio ) propionitrile having a melting point of 127 °- 128 ° c . to a mixture of 50 g of 3 -( 2 - aminothiazol - 4 - ylmethylthio ) propionitrile hydrochloride , 50 ml of isopropanol and 5 g of zinc oxide was added 100 g of an aqueous solution of 50 ( w / w )% cyanamide and then the mixture was refluxed for 24 hours . 50 g of an aqueous solution of cyanamide was added and refluxing the mixture for 12 hours was repeated twice . the reaction mixture thus obtained was concentrated under reduced pressure , insoluble matters thus precipitated were filtered away , and the filtrate was further concentrated under reduced pressure . water was added to the residue thus formed and after alkalizing the mixture by adding thereto 30 g of potassium carbonate , the product formed was extracted thrice with ethyl acetate . the organic layer thus formed was collected and washed with a saturated aqueous sodium chloride solution . then , 25 ml of an ethanol solution of 4 . 5 n hc1 was added to the organic layer , the mixture was cooled with stirring , and crystals thus deposited were collected by filtration to provide 31 g of 3 -( 2 - guanidinothiazol - 4 - ylmethylthio ) propionitrilehydrochloride having melting point of 137 to 140 ° c .