Salicylamide

B) Formamide, acetamide, oxamide, urea, benzamide, salicylamide thiourea. 

It frequently happens that more than one volatile product is evolved, a fact which may be of considerable value. For example, benzamide, CeHjCONHt, will give off first ammonia, and then benzonitrile and benzene on stronger heating salicylamide, HOC H CONHj, will give off ammonia and then phenol. Sulphanilamide, NH,C,H,SO,NH (p. 181), gives off ammonia and aniline. 

Aqueous solutions (when obtainable) give no reaction with ferric chloride. This is an important distinction from ammonium salts (sec above). Salicylamide, being also a phenol, is however an exception (p. 344). 

This experiment focuses on developing an HPLG separation capable of distinguishing acetylsalicylic acid, paracetamol, salicylamide, caffeine, and phenacetin. A Gjg column and UV detection are used to obtain chromatograms. Solvent parameters used to optimize the separation include the pH of the buffered aqueous mobile phase, the %v/v methanol added to the aqueous mobile phase, and the use of tetrabutylammonium phosphate as an ion-pairing reagent. 

Haddad and associates report the following capacity factors for the reverse-phase separation of salicylamide (k i) and caffeine... 

The popularity of aspirin has led to the preparation of a liost of relatively simple derivatives in the hope of finding a ilrug that would be either superior in action or better tolerated. i alicylamide (5), for example, is sometimes prescribed for pa-I Lents allergic to aspirin. It should be noted, however, that I his agent is not as active as the parent compound as an antiinflammatory or analgesic agent. This may be related to the fact I hat salicylamide does not undergo conversion to salicylic acid i 11 the body. 

Synthesis of the prototype begins with Friedel Crafts acetylation of salicylamide ( ). Bromination of the ketone (25) followed by displacement with amine gives the corresponding ami noketone ( ). Catalytic hydrogenation to the ami noalcohol completes the synthesis of labetolol (24). The presence of two chiral centers at remote positions leads to the two diastereomers being obtained in essentially equal amounts. 

Timolol maleate a-Bromoacetophenone Nomifensine maleate Bromoacetyl bromide Bromazepam Cephapirin sodium Clonazepam Flunitrazepam 5-Bromoacetyl salicylamide Labetalol HCI m-Bromoanisole Tramadol HCI p-Bromoanisole Cyclofenil Bromobenzene... 

The acetal 1, obtained from salicylamide and bromoacetaldehyde diethyl acetal, cyclizes on heating to provide l,4-benzoxazepin-5(4//)-one (2).32... 

A-Salicoyl derivatives of 3-amino-2-halopyridines cyclize under basic conditions to pyrido-[2,3-/ ][l, 4]benzoxazcpin-6(5//)-ones this has been shown for the cyclization of 7V-(2-chloro-4,6-dimethyl-3-pyridyl)salicylamide 41... 

A solution of A-(2-chloro-4,6-dimethyl-3-pyridyl)salicylamide (0.42 g, 1.52 mmol) in tetraethyleneglycol dimethyl ether (4 mL) was treated with NaOMe (0.123 g, 2.28 mmol) and the stirred mixture was heated at 220 JC for 3 h. It was cooled to 20 C, diluted with H20 (25 mL) and neutralized with 1 M HC1, when the product separated. An additional amount was obtained by extracting the filtrate with Et20 total yield 0.193g (53%) mp 242-244.5 C (aq EtOH). 

Salicylic acid for systemic use has been replaced by acetylsalicylic acid, amides of salicylic acid (salicylamide, ethenzamide, salacetamide), salsalate and diflunisal. 

Coricidin HBP Cold and Flu Tablets—chlorpheniramine maleate, acetaminophen Ed-Flex Capsules—phenyltoloxamine citrate, acetaminophen, salicylamide... 

Skeletal Muscle Relaxant Combinations Carisoprodol Compound—carisoprodol, aspirin Mexaphen—chlorzoxazone, acetaminophen Lobac—salicylamide, phenyltoloxamine, acetaminophen Norgesic Fbrte—orphenadrine citrate, aspirin, caffeine Norgesic—orphenadrine citrate, aspirin, caffeine Robaxisal—methocarbamol, aspirin Sodol Compound—carisoprodol, aspirin Soma Compound—carisoprodol, aspirin... 

C Hs03 119-36-8) see Acenocoumarol Olsalazine sodium Salbutainol Salicylamide 2-methyl-L-serine... 

Irreversible reaction of [18] iodine with acetylsalicylic acid, aethaverine, amidopyrine, ascorbic acid, benzo-caine, quinine, dihydrocodeine, fluorescein, glycine, hydrocortisone acetate, isoni-azid, metamizole, papaverine, paracetamol, phenacetin, phenol-phthalein, piperazine, resorcinol, salicylic acid, salicylamide, sulfaguanidine, thymol, triethanolamine, tris buffer detection by reaction chromatography... 

Fig. 19 Area under the salicylamide plasma concentrationtime curve (AUQ as a function of the oral dose of sodium salicylamide. Each point is the average of five subjects. (Based on data from Ref. 133.)...

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