Phosgene Immonium Chloride

The reaction of tertiary amides with phosgene immonium chloride (51) allows this approach to be extended to the synthesis of thiomalonamides (52 equation 23). ... 

Phenylurazole, 381 Phloroacetophenone dimethyl ether, 13 Phloroacetophenone trimethyl ether, 13 Phosgene, 26,94,157 Phosgene Immonium Chloride, 135 Phosphonitrilic chloride, 386-387 Phosphoric acid, 234, 235, 241, 302, 387 Phosphorus pentachloride, 388-389,401, 455,505... 

The Vilsmeier-Haack formylation procedure (Scheme 24) provides the most effective synthesis of formylpyrroles and indoles. Reaction of the heterocycles with the immonium cation (72), derived from DMF or (V-methylformanilide with an acid chloride, such as phosphorus oxychloride, thionyl chloride, phosgene, oxalyl chloride, benzoyl chloride or bromotriphenylphosphonium bromide, yields the intermediate heteroarylimmonium salt (73). Under suitable reaction conditions, this salt may be isolated from the reaction involving phosphorus oxychloride as an impure chlorophosphate (78TH30500) or precipitated from the reaction system as the thermally unstable perchlorate by the addition of sodium... 

Aus Phosgen-immonium-Salzen und Carbonsaure-dimethylamiden werden l,3-Bis-[dimethyl-amino]-l,3-dichlor-propenium-chloride erhalten, die mit Hydrazinen in 70 90% Ausbeute zu 3,5-Bis-[dimethylamino]-lH-pyrazolen cyclisieren (82-93%)405. 

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