Sodium amide reaction with, phosgene

Acetaldehyde reacts with phosphoms pentachloride to produce 1,1-dichloroethane [75-34-3] and with hypochlorite and hypoiodite to yield chloroform [67-66-3] and iodoform [75-47-8], respectively. Phosgene [75-44-5] is produced by the reaction of carbon tetrachloride with acetaldehyde in the presence of anhydrous aluminum chloride (75). Chloroform reacts with acetaldehyde in the presence of potassium hydroxide and sodium amide to form l,l,l-trichloro-2-propanol [7789-89-1] (76). 

The bicyclic meso-ionic 3-oxo-l,2,4-triazolo[4,5-a]pyridines (206) have been prepared by the following methods (i) the reaction of the hydrazines (207, X = H) with phosgene, (ii) heating the amide (207, X = CONH2) or the carbamate (207, X = COjEt), and (iii) alkylation or acylation of 3-oxo-l,2,4-triazolo[4,5-a]pyridine (208). The isomeric meso-ionic 2-oxo-l,3,4-triazolo[4,5-a]pyridines (209) are formed from the carbamoyl chlorides (210) and sodium azide. ... 

The use of activated anthranihc acid derivatives facUitates the preparation of the amides in those cases where the amines are either umeactive or difficult to obtain. Thus, reaction of (87-1) with phosgene gives the reactive the isatoic anhydride (89-1). Condensation of that with ortho-toluidine leads to the acylation product (89-2) formed with a simultaneous loss of carbon dioxide. This is then converted to the quinazolone (89-3) by heating with acetic anhydride. Reaction with sodium borohydride in the presence of aluminum chloride selectively reduces the double bond to yield the diuretic agent metolazone (89-4) [99]. 

A practically useful method for synthesis of selenoesters has been developed by Barton et al. A wide range of aliphatic and aromatic selenoesters have been synthesized from the appropriate N -disuh-stituted imidoyl chlorides (58) using sodium hydrogen selenide to introduce seleniumJ Imidoyl chlorides (58) can be obtained by the reaction of amides with phosgene. Representative results are shown in Scheme 17 (formulae 59-61). 

Phosgene reacts, sometimes violently, with a large number of common inorganic (Chapter 9) and organic (Chapter 10) substances. Hazardous reactions with lithium, sodium, potassium, aluminium, lithium amide, hexa-2,4-diyn-l, 6-diol, propan-2-ol, and hexafluoropropene have been mentioned specifically [1787]. Mixtures of potassium and phosgene are reported to explode when subjected to shock [1913a]. In addition, phosgene... 

By-products, including urea, are generated by reaction of the generated ammonia with unreacted phosgene. In contrast, gaseous phosgene reacts with solid sodium amide at 250 C to form sodium cyanamide [1605] ... 

---