GB629537A - Improvements in or relating to nitrogen and sulphur containing beta-substituted carboxylic acids and method of making same - Google Patents

Abstract

Compounds containing the groups <FORM:0629537/IV (b)/1> when treated with b -lactones yield the corresponding b -substituted-carboxylic acid <FORM:0629537/IV (b)/2> The preferred reaction is at 0-50 DEG C. between equimolar quantities of reactants dissolved in water although if either reactant is insoluble therein another polar solvent, e.g. ethyl alcohol, may be used. Nitrogen and sulphur containing reactants instanced are: thiourea, methyl-, N,N1-diethyl-, phenyl-, acetyl-, glycollyl-, malonyl-, carbamyl-, guanyl-, N,N1-diphenyl-, N,N-diphenyl-, sym-di-o-tolyl-, and benzyl-thioureas, thiohydantoic and trithiocyanuric acids, p thioallantoin, thioacetamide, thiobenzamide, thioacetanilide, thiooxamic acid and its esters, thio-carbazides, thiosemicarbazides, and thiuram sulphides and di-sulphides. b -lactones instanced are b -propriolactone which is preferred, b -butyrolactone, b - isobutyrolactone, b - valerolactone, b - isovalerolactone, b - n - caprolactone, a - ethyl - b -propiolactone, a -isopropyl-b -propiolactone, a -butyl-b -propiolactone, a -methyl-b -butyrolactone, a -ethyl-b -butyrolactone, b -methyl-b -valerolactone, b -cyclohexyl-b -propiolactone, a - and b -phenyl-b -propiolactone, b -benzyl-beta - propiolactone a ,a - dimethyl - b - propiolactone - b - carboxylic acids, trimethyl - b - propiolactone-a and b -carboxylic acids, b ,b -dimethyl-b -propiolactone-a - carboxylic acid, b ,D -dilactone of citrylidene malonic acid, a - or b -nitrophenyl-b -propiolactone, b -(2-nitro-3-chlorophenyl)-b -propiolactone, b -(2-nitro-3-methoxyphenyl)-b -propiolactone, a -hydroxy-b -phenyl-b -propiolactone and a -bromo-b ,b -dimethyl-b -propiolactone-a -carboxylic acid. In an example, b -propiolactone is added to an aqueous solution of thiourea and the product b -isothiourea-propionic acid filtered off and may be converted to thiohydracrylic acid by hydrolysing with sodium hydroxide and acidifying. Specification 649,028 is referred to.