Salicyloyl chloride

Salicylic alcohol glucosides, natural, 22 7 Salicyloyl chloride, 22 3 Salicylsalicylic acid, 22 16-17 physical properties of, 22 15t Saligenin, 22 23, 24 Salina salt, 5 788 Saline hydrides, 13 771 Saline solutions... 

Salicylic acid can be converted to salicyloyl chloride [1441-87-8] by reaction with thionyl chloride in boiling benzene. The formation of acyl halide may also extend to reaction with the phenolic hydroxyl. The reaction with phosphoms tri- and pentachlorides is not restricted to the formation of the acid chloride. Further interaction of the phosphoms halide and the phenolic hydroxyl results in the formation of the phosphoric or phosphorous esters. 

Fused oxygen and nitrogen-containing rings may also be prepared in reactions with thioureas thus, dihydrobenzoxazine products are obtained on treatment of salicyloyl chloride with thioureas371 or on fusion of salicylate esters with thiopseudoureas.320 When the thio-pseudoureas are treated with o-aminophenol, the products are benzoxa-zoles.320 A naphthyl analog of a benzoxazole is produced on treatment of l-(2-hydroxy-l-naphthyl)-2-thiourea with dimethyl sulfate.372... 

The most widely used method to prepare salicylanilides (35) involves condensation of an appropriate salicylic acid (33) with an aniline (34) in the presence of phosphorus trichloride [7,50-54] or phosphorus oxychloride [55] in boiling chlorobenzene, toluene or xylene. In these reactions salicyloyl chloride (36) is generated in situ, which then reacts with aniline to form 35. Alternatively salicyloyl chloride... 

A further application of the metal-template effect in the ortho-regioselective acylation of phenols is represented by the direct synthesis of salicyloyl chloride and derivatives by the reaction of bromomagnesium phenolates 4 with phosgene. The reaction affords the unstable salicyloyl chloride-magnesium complexes 5 by a pathway similar to the mechanism depicted in Scheme 5.2. These intermediates can be in situ converted into the corresponding acids 6 (Scheme 5.3), esters, amides, or ketones by reaction with suitable reagents. 

The 2- and 3-deoxy-D-er> f/i/-o-pentosyl derivatives of 4-amino-5-ethoxy-carbonylimidazole (45) have been prepared from the corresponding ribofuranosyl derivative via l - and 3 -chloro-nucleosides prepared by treatment with O-acetyl-salicyloyl chloride. Scheme 8 shows the reaction of cytosine with thionyl chloride giving 5 -chloro-5 -deoxy-ribo- and -arabino-analogues, which were then... 

A mixture of thiobenzophenone and salicyloyl chloride heated 6 hrs. at 100-120° under Ng until HCl-evolution ceases 2,2-diphenyl-l,3-benzoxathian>4-one. Y 80%. F. e., also 3,l-benzoxathian-4-ones, s. H. Tokunaga, T. Kawashima, and N. Inamoto, Bull. Chem. Soc. Japan 45, 2220 (1972). 

N,N -bis(salicyloyl)hydrazide can be prepared through the reaction of a salicylic acid alkyl ester and hydrazine. Alternatively, a thionyl chloride route is viable (4). Detailed examples of the synthesis are given in the literature (5). 

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