AMINO ACIDS: IV. THE REACTION OF GLYCINE AND β-ALANINE WITH CARBON DISULPHIDE

Abstract

Glycine and β-alanine on condensation with carbon disulphide gave the corresponding l,3-di-(carboxyalkyl) thioureas. l,3-Di-(carboxymethyl) thiourea is rearranged to 2-thio-3-(carboxymethyl) hydantoin by warming with hydrochloric acid solution or heating above its melting point. Evidence is presented for the reversible condensation of 2 mole equivalents of the sodium salt of 2-thio-3-(carboxymethyl) hydantoin by the elimination of water. This condensation product is obtained as well-defined pink crystals. l,3-Di-(β-carboxyethyl) thiourea was oxidized with an alkaline solution of hydrogen peroxide or sodium hypochlorite solution to l,3-di-(β-carboxyethyl) urea. l,3-Di-(β-carboxyethyl) thiourea and l,3-di-(β-carboxyethyl) urea have been cyclized by heating with p-toluenesulphonic acid. The products were 2-thio-3-(β-carboxyethyI) hydrouracil and 3-(β-carboxyethyl) hydrouracil respectively.