Journal of Synthetic Organic Chemistry, Japan
Online ISSN : 1883-6526
Print ISSN : 0037-9980
ISSN-L : 0037-9980
Synthetic Studies on Carbamoyl-O-methylisourea
Kokoro IIOEiichi ICHIKAWAKeijiro ODO
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1974 Volume 32 Issue 7 Pages 513-518

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Abstract
Improved methods for the preparation of carbamoyl-O-methylisourea (CMI) and N-carbamoyl compounds of cyanamide derivertives using CMI were investigated.
The reaction of cyanourea copper salt with methanol gave CMI copper complex, which was converted by treatment with H2S to CMI in good yield.
1-Thioallophanic acid O-methyl ester was obtained by the reaction of CMI with H2S in aqueous solution at room temperature.
CMI was hydrolyzed or decomposed in acidic or alkaline medium to biuret, methylallophanate and cyanourea.
CMI salt reacted with methylamine to give methylguanylurea salt in good yield, but no reaction occurred with aniline.
Carbamoylmelamine was obtained by the reaction of CMI with biguanide at room temperature, and cyanoguanylurea was obtained with cyanamide in good yield in the same manner.
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© The Society of Syhthetic Organic Chemistry, Japan
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