Dithiocarbamates reaction with, phosgene

Other preparative routes to isothiocyanates involve reaction of amines with carbon disulfide and alkali and subsequent treatment of the dithiocarbamate (112) with phosgene or ethyl chloroformate. Alternatively, the dithiocarbamate may be reacted with mercury(II) chloride or lead tetranitrate (Scheme 61). Amines can also be reacted with thiophosgene or N,N-diethyl thiocarbamoyl chloride (113) (Scheme 61). 

In an extension of this triazine synthesis, dithiocarbamates 8, rather than amides, can be employed. In this case the corresponding imidium salts are obtained by reaction of the dithiocarbamates with phosgene or chlorine.395 396... 

Dithiocarbamic salts are suitable starting materials for the preparation of isothiocyanic esters (mustard oils), their reactions with heavy-metal salts,771 chloroformic esters,772 phosgene,768 carbodiimides,805 phosphorus oxychloride,806 aryl cyanates,732 or sodium hypochlorite807 usually giving good yields. Reaction of amines 808,809 or their hydrochlorides with thiophosgene810 is also generally applicable. 

The reaction of V-cyanocarboximidamide with (chloromethylene)iniinium salts provides another important route to substituted 1,3,5-triazines.394,395 The (chloromethylene)iminium salts are prepared in situ from the corresponding amides, thioamides or dithiocarbamates and phosphoryl chloride, phosphorus pentachloride or phosgene (cf. Houben-Weyl, Vol. E5,... 

---