ChemicalBook CAS DataBase List N-cyano-N'-methylguanidine

N-cyano-N'-methylguanidine synthesis

5synthesis methods

Product Name:N-cyano-N'-methylguanidine
CAS Number:1609-07-0
Molecular formula:C3H6N4
Molecular Weight:98.11

593-51-1 Synthesis

593-51-1
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Yield:1609-07-0 77%

Reaction Conditions:

with diethyl ether in butan-1-ol;Reflux;

Steps:

1 (IVa) N-cyano-N’ -methylguanidine.

General procedure: General Procedure (A) : synthesis of intermediates of Formula (IV) - Step 1, Scheme 1.To a suspension of sodium dicyanamide (V) (1.2 eq.) in 1-butanol (1.2 M), was added the proper amine hydrochloride (VI) (1.0 eq.). The resulting mixture was heated at refluxfor 6-8 hours, affording a white precipitate, which was filtered off. The filtrate was concentrated under vacuum to yield crude cyanoguinidine (IV) . Further purification by flash chromatography was performed when required; (IVa) N-cyano-N’ -methylguanidine.The title compound was obtained according to general procedure A using methylamine hydrochloride (0.63 g, 9.30mmol) . The crude material was triturated with Et20, affording IVa as a yellow oil, which was used in the next step without further purification: 0.72 g (77%) . (CD3OD, 400 MHz) 6 2.74 (s, 3H) . 13C-NNR (CD3OD, 100 MHz) 628.4, 120.2, 163.4.

References:

WO2015/189830,2015,A1 Location in patent:Page/Page column 39; 40