The reaction between acetamide and alkyl bromides, showing its general applicability to the synthesis of substituted acetamides and the corresponding amines, has been investigated.A possible mechanism for the reaction, accounting for the production of ammonium bromide, has been suggested.1. 2.During a study of the pharmacological properties of some iso-urea derivatives, it was found by one of us1 that carbethoxy-ethyl-isourea had well-marked physiological action, the chief effects being a mild central depression, a rapid and considerable fall of body temperature, and an increased muscle tonus. The muscular hypertonus suggested an action similar to that of guanidine which is known to stimulate the myo-neural receptors2It was decided for the purpose of a comparative study to prepare the mono-and dicarbethoxy-guanidines (guanidine mono-and di-formic esters) and examine their pharmacological properties. At the same time it was thought desirable to prepare the dicarbethoxy-ethyl-iso-urea, to determine the effect of introducing a second carbethoxy group into the iso-urea molecule. The compounds may be regarded as urethans, and the study of them is therefore included in a series of studies being carried on in this Laboratory on the chemistry and pharmacology of some mono-and diurethans. Formulas I and I1 show the structures of the iso-urea derivatives and I11 and IV the structures of the carbethoxy-guanidines. /NH.COOC*Hs C-OCeH5 ~N H /NH.COOCzHb \N.COOC~HB C-OCzH5
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