50909-46-1Relevant academic research and scientific papers
Chlorotrimethylsilane activation of acylcyanamides for the synthesis of mono-N-acylguanidines
Looper, Ryan E.,Haussener, Travis J.,MacK, James B. C.
, p. 6967 - 6971 (2011/10/04)
A simple and efficient one-pot method for the synthesis of monoprotected guanidines is presented. Treatment of an acylcyanamide with chlorotrimethylsilane generates a reactive N-silylcarbodiimide capable of guanylating a variety of amines. Typically the reaction is complete in 15 min for primary and secondary aliphatic amines at rt. Hindered amines and anilines are also competent nucleophiles but require extended reaction times.
SYNTHESIS OF ALKYL N-CYANO-N-SUBSTITUTED CARBAMATES AND N,N-DISUBSTITUTED CYANAMIDES
Suba, Lydia,Schafer, Tann,Ruminski, Peter G.,D'Amico John J.
, p. 219 - 226 (2007/10/02)
The reaction of S,S' methyl cyanodithioimidocarbonate with potassium hydroxide in alkyl or benzyl alcohol furnished the O-alkyl and benzyl O-potassium cyanoimidocarbonates (1-5).The reaction of the potassium salts (1, 3, or 4) with 10 percent excess of alkyl, allyl or benzyl halides afforded the unknown titled carbamates (6-17).The reaction of 2 with 10 percent excess benzyl bromide or 5 with 10 percent excess methyl iodide gave the same product, N-benzyl-N-methyl cyanamide (18).The reaction of 2 with 10 percent and 55 percent excess allyl bromide afforded N-allyl-N-methyl cyanamide (19) and N,N-diallyl cyanamide (20), respectively.The reaction of 3 with 28 percent excess of allyl iodide furnished N-allyl-N-propyl cyanamide (21). Possible mechanisms and supporting NMR, IR and mass spectra data are discussed.
