Sodium /7-toluenesulfonamide

In a typical experiment, triethylene glycol was treated with two equivalents of sodium toluenesulfonamide in dry DMF solution. After 6 h at reflux, the solution was distilled and product obtained by a standard work-up procedure. By this procedure, 9 was obtained in about 10% yield. The transformation is illustrated below as Eq. (4.10). Note also that Vogtle and his coworkers have also utilized phthalimide as a source of nitrogen in the preparation of such azacrown precursors as H2N(CH2CH2 0)2CH2CH2NH2 In such reactions, a standard hydrazine cleavage was used to remove the phthaloyl residue. 

OtherH-Chloro Compounds. Sodium N-chlorobenzenesulfonamide (chloramine B) [127-52-6] (4), sodium A/-chloro-/)-toluenesulfonamide (chloramine T) [127-65-1] (5), /V-cb1orosuccinimide [128-09-6] (6), and tricbloromelamine [12379-38-3] (7) have also had minor roles as bleaching agents. 

Chloramine-T, sodium A/-chloro-/)-toluenesulfonamide [127-65-17, was widely used during World War I for the treatment of infected wounds, and subsequentiy for hygienic purposes such as mouthwashes, douches, etc. It can be used for sanitising food-handling equipment, but its activity is considerably slower than that of hypochlorites. The Grade A Pasteurized Milk Ordinance (1985) and the Ordinance and Code for Restaurants (1948) of the U.S. Pubhc Health Service permitted the use of chloramine-T. 

Chloramine-T (A -chloro-p-toluenesulfonamide sodium salt) 3H2O [7080-50-4] M 281.7, m 168-170°(dec). Crystd from hot water (2mL/g). Dried in a desiccator over CaCh where it loses water. Protect from sunlight. Used for detection of bromate and halogens, and Co, Cr, Fe, Hg, Mn, Ni and Sb ions. 

The method illustrates the ability of the sodium hydride-dimethylformamide system to effect the alkylation of aromatic sulfonamides under mild conditions and in good yield. The method appears to be fairly general. The submitters have prepared N,N-diethyl- and N,N-di- -butyl- >-toluenesulfonamide as well as 2-(/ -tolyIsuIfonyl)benz[/]isoindoline from 2,3-bis-(bromomethyl)naphthalene, and 1 %-tolylsulfony])pyrrolidine from 1,4-dichIorobutane the yield of purified product exceeded 75% in each case. 

Sodium dodecyl sulfate and hydrogen dodecyl sulfate have been used as catalysts in the denitrosation iV-nitroso-iV-methyl-p-toluenesulfonamide [138]. The kinetics of condensation of benzidine and p-anisidine with p-dimethylamino-benzaldehyde was studied by spectrophotometry in the presence of micelles of sodium dodecyl sulfate, with the result that the surfactant increases the rate of reaction [188]. The kinetics of reversible complexation of Ni(II) and Fe(III) with oxalatopentaaminecobalt(III) has been investigated in aqueous micellar medium of sodium dodecyl sulfate. The reaction occurs exclusively on the micellar surface [189]. Vitamin E reacts rapidly with the peroxidized linoleic acid present in linoleic acid in micellar sodium dodecyl sulfate solutions, whereas no significant reaction occurs in ethanol solution [190]. 

C7H9NO2S 88-19-7) see Saccharin Zafirlukast p-toluenesulfonamide sodium salt see under p-toluenesulfamide sodium salt p-toluenesulfonic acid... 

Amino-Hydroxylation. A related reaction to asymmetric dihydroxylation is the asymmetric amino-hydroxylation of olefins, forming v/c-ami noalcohols. The vic-hydroxyamino group is found in many biologically important molecules, such as the (3-amino acid 3.10 (the side-chain of taxol). In the mid-1970s, Sharpless76 reported that the trihydrate of N-chloro-p-toluenesulfonamide sodium salt (chloramine-T) reacts with olefins in the presence of a catalytic amount of osmium tetroxide to produce vicinal hydroxyl p-toluenesulfonamides (Eq. 3.16). Aminohydroxylation was also promoted by palladium.77... 

Sodium AT-chloro-AT-alkylsulfamates, 13 108 Sodium IV-chloro-p-toluenesulfonamide (chloramine T), 4 54 Sodium chromate... 

Dichloroacetamide has been prepared from ethyl dichloroace-tate with alcoholic ammonia1 or aqueous ammonium hydroxide,2 from ethyl dichloromalonate and alcoholic ammonia,3 by the action of ammonia on pentachloroacetone,4 chloral cyanohydrin,5 and hexachloro-i,3,5-cyclohexanetrione,6 from chloral ammonia and potassium cyanide,7 by the action of hydrogen chloride on dichloroacetonitrile,8 from the reaction of asparagine with the sodium salt of N-chloro- -toluenesulfonamide,9 and by the action of an alkali cyanide and ammonia on chloral hydrate.10... 

Sodium N -chlorobenzenesulfonamide, 2229 Sodium N -chloro-4-toluenesulfonamide, 2739 N,N,N",N" -Tetrachloroadipamide, 2370... 

Alkylation of 7V-benzyl-p-toluenesulfonamide (12a) with a threefold excess of fra j-l,4-dichloro-2-butene (ila) gives the allylic chloride 11b. which is treated with sodium acetate in DMF followed by hydrolysis to afford the allylic alcohol 10a in an overall 68% yield. 

H, Cl, Br, NO2, Me, MeO) by bromamine-B, catalysed in the presence of HCl in 30% aqueous methanol by RuCls have been smdied and a biphasic Hammett a-relationship derived. A kinetic study of the ruthenium(in)-catalysed oxidation of aliphatic primary amines by sodium A-bromo-j -toluenesulfonamide (bromamine-T, BAT) in hydrochloric acid medium has been undertaken and the mechanism of the reaction discussed. A concerted hydrogen-atom transfer one-electron transfer mechanism is proposed for the ruthenium(in)-catalysed oxidation of 2-methylpentane-2,4-diol by alkaline hexacyanoferrate(III). The kinetics of the oxidation of propane-... 

The most common method of radiolabeling employs Chloramine-T, the sodium salt of the N-monochloro derivative of p-toluenesulfonamide (Fig. 17). It breaks down slowly in aqueous solution to hypochlorous acid and is used as a mild oxidizing agent in radioiodination reactions. Other oxidation reagents used in radioiodination include... 

Primary ally lie amines1 In the presence of this catalyst, allylic chlorides or acetates react with sodium p-toluenesulfonamide in THF/DMSO (80 20) to form the corresponding allylic sulfonamide in 60-85% yield. The products are converted into primary allylic amines on reductive cleavage (sodium naphthalenide). 

The kinetics of oxidation of caffeine by sodium IV-bromo-p-toluenesulfonamide (bromamine-T) in dilute HC1 have been studied.138 In the oxidation of a-phenylbenzenemethanols by bromamine-T catalysed by ruthenium(III), the reaction constant p is —2.1 for electron-releasing substituents.139 It is proposed that the... 

Sodium N-chloro-4-toluenesulfonamide, 2735 Sodium IV-chlorobenzenesulfonamide, 2222 N,N,N, N" -Tetrachloroadipamide, 2363 Tetrafluoroammonium hexafluoromanganate, 4378 Tetrafluoroammonium hexafluoronickelate, 4379 Tetrafluoroammonium octafluoroxenate, 4380 Tetrafluoroammonium perbromate, 0242 Tetrafluoroammonium perchlorate, 3980 Tetrafluoroammonium tetrafluoroborate, 0133 Tetrafluorodiaziridine, 0350 f Tetrafluorohydrazine, 4339... 

Tolylsulfonyl)dihydroisoindole has been prepared by alkylation of j>-toluenesulfonamide with o-xylylene dibromide in the presence of sodium methoxide in ethanol.2,8... 

Reaction of the diol with p-toluenesulfonyl chloride in pyridine, however, produced the ditosylate in nearly quantitative yield. SN2 displacements by chloride on neopentyl tosylate, which bears certain structural similarities to the ditosylate precursor of CAMPHOS, have been shown to give good yields of neopentyl chloride. However, when l,2,2-trimethyl-l,3-bis(hydroxymethyl)-cyclopentane ditosylate was allowed to react with sodium chloride in hexa-methylphosphoramide, in an attempt to form the dichloride, only N, A -dimethyl-p-toluenesulfonamide was isolated. Reaction of the ditosylate with lithium chloride in ethoxyethanol was exothermic and HC1 was evolved but the dichloride was not isolated. The isolated product contained at least one oleflnic bond. Similarly, in N, TV-dimethylformamide, lithium chloride and the ditosylate gave a product that decomposed on distillation. Faced with such repeated failures, a dihalide route to CAMPHOS was abandoned in favor of a more direct approach reaction of the ditosylate with diphenylphosphide anion. 

Sodium TV-chloro-/ -toluenesulfonamide (chloramine T, CAT) is a stable N—Cl derivative, which has been widely used in organic synthesis, particularly as an oxidant768. Kinetic study on the chlorination of / -aminobenzoic acid by CAT reveals simultaneous catalysis by H+ and Cl"769. 

Chloramine-T trihydrate p-Toluenesulfonamide, A-chloro-, sodium salt (8) Benzenesulfonamide, A-chloro-4-methyl-, sodium salt, trihydrate (9) (7080-50-4)... 

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