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Topic: Conversion of thiourea to urea  (Read 6078 times)

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Offline Silden

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Conversion of thiourea to urea
« on: March 27, 2011, 10:33:46 AM »
When I am reacting an amine with isothiocyanate in THF I get both the urea and thiourea products. But when the reaction is performed in DCM only the thiourea is obtained.

Can someone help me with a possible reaction mechanism for the conversion of thiourea to urea in the presence of isothiocyanate and THF (not dry - may contain water)
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Offline Honclbrif

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Re: Conversion of thiourea to urea
« Reply #1 on: March 27, 2011, 12:11:10 PM »
Do you smell any H2S? It may just be a standard aqueous hydrolysis reaction. Water acts as a nucleophile, tetrahedral intermediate, collapse eliminates hydrogen sulfide.
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