O-Methylisourea hydrochloride synthesis

Yield:5329-33-9 100%

Reaction Conditions:

with acetyl chloride at 0 - 20; for 60 h;Inert atmosphere;

Steps:

Methyl carbamimidate hydrochloride (9)
AmethanolicHClsolutionwaspreparedat0°Cbyadditionofacetylchloride(1.98mL,27.5mmol,1.18eq)to5mLofMeOH.Thiswasslowlyaddedtoamixtureofcyanamide(1.00g,23.3mmol)inMeOH(3mL)at0°C,maintainingthereactionmixtureatrtduringtheaddition.Thereactionwaswarmedtortandstirredfor2.5d,torevealawhitesolid.Thereactionmixturewasthenconcentrated,andthewhitesolidobtaineddriedundervacuumovernightinthepresenceofP2O5andKOHtoprovidemethylcarbamimidatehydrochloride(9,2.95g,24.0mmol,quant)

References:

Manos-Turvey, Alexandra;Al-Ashtal, Hiba A.;Needham, Patrick G.;Hartline, Caroll B.;Prichard, Mark N.;Wipf, Peter;Brodsky, Jeffrey L. [Bioorganic and Medicinal Chemistry Letters,2016,vol. 26,# 20,p. 5087 - 5091] Location in patent:supporting information

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