Studies in Urethans. Iii. The Preparation of Various Substituted Urethans

Abstract

As part of a study of the chemistry and pharmacology of urethans, a number of substituted urethans have been prepared in this Laboratory, and it seemed desirable to record those that have not previously been described in the literature, and to describe improved or modified methods of preparation for some that have been reported already.These compounds have been prepared (1) by treating a solution of an amine in ether or benzene with the required amount of alkyl chlorocarbonate in the presence of an aqueous solution of sodium or potassium hydroxide, or (2) by heating together an amino compound and an alkyl chlorocarbonate with or without a solvent, or (3) by heating together a urethan with an acid chloride with or without a solvent.Preliminary observations on the pharmacological properties of some of these compounds are included in this paper but detailed studies will be reported elsewhere.

Synthesis and In Vitro Antimycobacterial Activity of Novel N-Arylpiperazines Containing an Ethane-1,2-diyl Connecting Chain

“…Melting point (Mp or mp) values of prepared intermediates and final compounds, respectively, were determined on the Kofler hot plate apparatus HMK (Franz Kustner Nacht GK, Dresden, Germany) and left uncorrected. The mps of some intermediates were already published, i.e., 3a : 102–104 °C [ 64 ]; 3b : 111–112 °C [ 64 ] and 113–114 °C [ 65 ], respectively; 3d : 53–55 °C [ 64 ]; 3e : 168 °C [ 64 ] and 160–162 °C [ 66 ], respectively; 3f : 158 °C [ 67 ], 157–158 °C [ 68 , 69 ] and 160–161 °C [ 64 ], respectively; 3h : 87–88.5 °C [ 64 ]; 4a : 99–103 °C [ 70 ]; 4b : 108–110 °C [ 71 ]; 4d : 80–86 °C [ 70 ]; 4e : 200–201 °C [ 72 ].…”

Synthesis of N-Monomethyl- and N,N-Dimethylcephalins

“…(3-Bromoethylphosphoryldichloride was prepared as described by Jean (1957); bp 76°/2 mm. iV-Methylbenzylamine (bp 45-47 °,2 mm; hydrochloride, mp 176-177°) was obtained in yields of about 70% either from AT-benzylurethan (Basterfield et al, 1926) or from iV-methylbenzamide by reduction with lithium aluminum hydride (Wessely and Swoboda, 1951) in hot tetrahydrofuran. Chloroform was distilled over phosphorus pentoxide.…”