An efficient procedure for traceless solid-phase synthesis of N,N'-substituted thioureas by thermolytic cleavage of resin-bound dithiocarbamates.
A novel and efficient procedure which is compatible with high-throughput process for the traceless solid-phase synthesis of thioureas is described. In the presence of carbon disulfide, Merrifield resin reacts with an amine to give a resin-bound dithiocarbamate moiety. Heating this supported dithiocarbamate in the presence of a second amine at 60 degrees C for 12 h led to the formation of the thiourea with the release of benzylthiol bound to the resin. This process allows the preparation of N,N'-di- and trisubstituted thioureas in good yields and with satisfactory purity. Furthermore, the mild reaction conditions involved are compatible with many functional groups.
Gomez
L
L
Laboratoire de Synthèse Bioorganique, Université Louis Pasteur de Strasbourg, Unité associée au CNRS, UMR 7514 Faculté de Pharmacie, Illkirch, France.
Gellibert
F
F
Wagner
A
A
Mioskowski
C
C
D005609:Free Radicals; D012116:Resins, Plant; D013816:Thermodynamics; D013859:Thiocarbamates / Q000737:chemistry*; D013890:Thiourea / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry
D005609:Free Radicals; D012116:Resins, Plant; D013859:Thiocarbamates; D013890:Thiourea