Sodium amide chloride

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). 

Phosphoms trichloride and pentachloride form sodium chloride and sodium phosphide, respectively, in the presence of sodium. Phosphoms oxychloride, POCl, when heated with sodium, explodes. Carbon disulfide reacts violendy, forming sodium sulfide. Sodium amide (sodamide), NaNH2, is formed by the reaction of ammonia gas with Hquid sodium. SoHd sodium reacts only superficially with Hquid sulfur dioxide but molten sodium and gaseous... 

Ring Additions Catalyzed by Alkali Metals. The addition of tributyltin chloride and olefins such as styrene, isoprene, or butadiene to sulfolane is cataly2ed by alkah metals, including sodium and lithium, and by sodium amide (10—13). The addition of tributyltin chloride to sulfolane in the... 

Several triazinyl ketones isomerize to 4-acetamidopyrimidines. TTiis is seen in the C-acylation of 2,4,6-trimethyl-l,3,5-triazine (708) with benzoyl chloride in the presence of sodium amide to give the ketone (709) which undergoes a Dimroth-like rearrangement in boiling water to afford A-(2-methyl-6-phenylpyrimidin-4-yl)acetamide (710) it can be seen that the acylating agent determines the identity of the 6-substituent 64JHC145). 

In an unusual variant on the Chichibabin reaction, treatment of 3-hydroxypyridine with sodium amide at 200° affords 2,6-di-aminopyridine (21). Coupling of the product with benzenediazo-nium chloride gives phenazopyridine (22). This drug is used as an analgesic for the urinary tract in conjunction with antibacterial agents for treatment of urinary infections. 

Nucleophilic aromatic substitution of the anthranilic acid derivatives, 72, on ortho-bromonitrobenzene affords the diphenyl-amine, 73. The ester is then saponified and the nitro group reduced to the amine (74). Cyclization of the resulting amino acid by heat affords the lactam (75). Alkylation on the amide nitrogen with 2-dimethylaminoethyl chloride by means of sodium amide affords dibenzepine (76). ... 

Sulfuric Acid Sodium Amide Dimethylaminoethyl Chloride... 

Initialiy, 4-bromobenzyl-cyanide is reacted with sodium amide and 2-chloropyridine to give bromophenyl-pyridyl acetonitrile. This is then reacted with sodium amide then dimethyi amino ethyl chloride to give 4.bromophenyl-dimethylamlnoethyl-pyrldyi acetonitrlie. This intermediate is then hydrolyzed and decarboxylated to bromphenirame using 80% H2SO4 at 140°-150°C for 24 hours. The brompheniramine maieate may be made by reaction with maleic acid in ethanol followed by recrystallization from pentanoi. 

Raw Materials Methyl chloride 4-Chlorobenzophenone Magnesium Sodium amide ... 

Sodium amide Sulfuric acid Hydrogen chloride... 

Diethanol methylamine Sodium amide Sulfuric acid Hydrogen chloride Thionyl chloride Benzyl cyanide Ethanol ... 

N-(2-Pyridylmethy Dan nine Sodium amide 2-Piperidinoethyl chloride... 

To a stirred suspension of 4.29 g (0.11 mol) of sodium amide in 100 ml of dry toluene was added 19.9 g (0.1 mol) of phenothiazine. The solution was heated at reflux for two hours, the sodium salt of phenothiazine precipitating from solution. The toluene suspension of the sodium salt of phenothiazine was cooled to room temperature, whereupon there was added dropwise with continued stirring 13.36 g (0.1 mol) of /3-pyrrolldinoethyl chloride in 50 ml of dry toluene. After addition was complete, the solution was heated under reflux, with stirring, for an additional 15 hours. Upon cooling, the toluene was extracted with dilute hydrochloric acid and the toluene then discarded. The aqueous acid solution was made alkaline with dilute sodium hydroxide, the crude N-(j3-pyrrolidinoethyl)-phenothiazine separating as a brownish oil. 

V-Aminoalkylation of 5/f-dibenzo[4/][l,3]diazcpin-6(7//)-ones 17 is accomplished by successive treatment with sodium amide and a (dialkylamino)alkyl chloride. Selected examples are given yields were not reported.179 ... 

Sebacic add, 43, 39 Sebacoyl chloride, 43, 37 2,2 -Sebacoyldicyclohexanone, 43, 34 Sodium amide, as catalyst for carbona-tion of methylacetylene, 42, 98... 

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