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Chemistry Forums for Students => Organic Chemistry Forum => Organic Chemistry Forum for Graduate Students and Professionals => Topic started by: Silden on March 27, 2011, 10:33:46 AM

Title: Conversion of thiourea to urea
Post by: Silden 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)

Title: Re: Conversion of thiourea to urea
Post by: Honclbrif 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.