http://rdf.ncbi.nlm.nih.gov/pubchem/patent/US-6100428-A

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filingDate 1999-10-06-04:00^^<http://www.w3.org/2001/XMLSchema#date>
grantDate 2000-08-08-04:00^^<http://www.w3.org/2001/XMLSchema#date>
inventor http://rdf.ncbi.nlm.nih.gov/pubchem/patentinventor/MD5_de458a8ad429ee38d3d4baa011a4ca9c
http://rdf.ncbi.nlm.nih.gov/pubchem/patentinventor/MD5_bb2a371efb41165732738a6a2366b5d8
publicationDate 2000-08-08-04:00^^<http://www.w3.org/2001/XMLSchema#date>
publicationNumber US-6100428-A
titleOfInvention Nickel promoted guanylation of amines with isothioureas and thioureas
abstract An improved method for guanylating amines is provided. Broadly, the amines are reacted with a guanylating agent in the presence of a nickel catalyst. Preferably, the nickel catalyst comprises nickel in the zero oxidation state. Suitable nickel(0) catalysts are derived from nickel-boride alloys, nickel-phosphide alloys, aluminum-nickel alloys, nickel on kieselguhr, and nickel on silica/alumina catalysts. Preferred guanylating agents are thioureas and isothioureas. In one embodiment, protecting groups are selectively attached to the guanylating agents to yield particular substituted guanidines. The preferred protecting groups are Boc groups, Cbz groups, and arylsulfonyl groups. The reactions are particularly well suited for guanylating primary and secondary amines. The methods of the invention can be carried out under ambient conditions to provide high yields of the corresponding guanidines, with the nickel catalyst being essentially completely recoverable for reuse.
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