Palau'chlor

[1596379-00-8] C5H8ClN3O4 (MW 209.59) InChI = 1S/C5H8ClN3O4/c1-12-4(10)7-3(9-6)8-5(11)13-2/h1-2H3,(H2,7,8,9,10,11) InChIKey = PCUVYBUDIWDLNI-UHFFFAOYSA-N (replacing hydrogen atoms in heterocycles with chlorine atoms in one step1) Alternate Name: 2-chloro-1,3-bis(methoxycarbonyl) guanidine, CBMG. Physical Data: mp 109–110 °C.1 Solubility: soluble in CH2Cl2, CHCl3; partially soluble in acetonitrile, DMSO; insoluble in MeOH, EtOH. Form Supplied in: free-flowing white powder. Analysis of Reagent Purity: Palau'chlor has been characterized by HRMS, IR, 1H, 13C NMR, and X-ray crystallography.1 Preparative Methods: Palau'chlor can be prepared in three steps on decagram scale (eq 1). Step 1: Starting from commercially available S-methylisothiourea sulfate, methoxycarbonylation is accomplished by slowly adding excess methyl chloroformate under basic conditions at 0 °C and subsequently warming to room temperature.1, 2 Step 2: Nucleophilic substitution is achieved by using a freshly prepared solution of NH3 in MeOH. During this step, the reaction mixture remains turbid and is allowed to proceed at ambient temperature overnight. Step 3: The obtained N,N′-bis(methoxycarbonyl)guanidine is reacted with freshly prepared t-BuOCl3 to give pure Palau'chlor quantitatively (eq 1).1 (1) Handling, Storage, and Precautions: Palau'chlor is a free-flowing powder that can be stored under air and without any precautions.