Sodium p-toluenesulfonamide

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). 

Although a variety of primary and secondary amines can be utilized as nitrogen nucleophiles, amina-tion of allylic substrates with ammonia has been reported to be unsuccessful. Therefore, bis(p-methoxy-phenyDmethylamine, sodium p-toluenesulfonamide or sodium azide have been utilized instead of ammonia. In the presence of a palladium catalyst, imides, such as phthalimide, react with allylic esters with the exception of geranyl and linalyl acetates. 0-Geranyl- and 0-linalyl-isourea derivatives, however, reacted with phthalimide giving the expected -allylic phthalimides in 65% and 71% yields, respectively. ... 

Amides, carbamates, imides, and their metal salts also serve as reactive nucleophiles (Scheme 3). Sodium p-toluenesulfonamide attacks l-acetoxy -chloro-cyclohex-2-ene to give an allylic amide in a highly chemoselective manner with retention of conflgura-tion.t Sodium salt of methylcarbamate is also alkylated in DMSO or HMPAJ ° (A, 0)-Bis-fer-Boc hydroxylamine reacts with an aUylic carbonate chemo- and regioselectively to provide a protected A-allylhydroxylamine, in which an ethoxy anion, a counterion of Pd in a 7r-allylpalladium complex, serves to generate an anion of (A, 0)-bis-ter-Boc hydroxylamine.f Preparation of primary allylamines by a selective monoallylation of ammonia is not possible and they are prepared by indirect methods. The monoallylation... 

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. 

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... 

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. 

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... 

OtherN-Chloro Compounds. Sodium N-chlorobenzenesulfonamide (chloramine B) [127-52-6] (4), sodium AJ-chloro-p-toluenesulfonamide (chloramine T) [127-65-1] (5), N-chlorosuccinimide [128-09-6] (6), and trichloromelamine [12379-38-3] (7) have also had minor roles as bleaching agents. 

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... 

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. 

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

I HIOL ESTERS, 61,48 preparation of, 61, 134 Thiophosgene, 61, 71 Titanium chloride [7705-07-9], 60, 113 Titanium trichloride, 60. 113 p-Toluenesulfonamide,, V-chloro-, sodium salt. 61, 85... 

An aqueous solution of di(triethylamonium) dodecahydro-ctoio-dodecaborate(2-), (EtjNH)2Bl2H12, (10 pi, lmg/ml) and an astatine solution in methanol (5 pi) were added to 30 pi of buffer solution (pH 7.5). Labelling was started by addition of 10 pi of solution of the sodium salt of A chloro-p-toluenesulfonamide, Chloramine T, (5 mg/ml in water). The mixture was vortexed for a few seconds and left to react for 5 min. The reaction was quenched with 20 pi of solution of sodium metabisulfite, Na Oj, (4 mg/ml in water). Sodium iodide, Nal, (5 pi, 20 mg/ml in water) was added as carrier before analysis. 

AMINO GROUP Boron trifluoride ether-ale. l-r-Bulyloxycarbonyltriazole-1,2,4, Di-t-butyl dicarbonate. 4-Dimethylamino-1-t-butyloxycarbonyl pyridinium chloride. CARBONYL GROUP Ceric ammonium nitrate. 1,2-Dihydroxy-3-bromopropane. Sodium N-chloro-p-toluenesulfonamide. Thallium(lll) nitrate. Trichloroethanol. Trimcthylsilyl cyanide. Chloromethyl methyl sulfide. N,N -Diisopropylhydra-zinc. Trichloroethanol. 

The following procedure has been used by Hartmann (1963) to prepare alcohol-free C-diazomethane in about 60-65% yield. N-Methyl-C -N-nitroso-p-toluenesulfonamide (22 mg, 0.103 mmole, 0.1 mC of C " ) was dissolved in 1 ml of anhydrous, peroxide-free diethyl ether in a 5-ml distilling flask fitted with a gas inlet tube. The side arm was bent vertically downward near the top and connected through a two-holed rubber stopper to a 10-ml Erlenmeyer flask. A tube from the second hole led to the back of the hood. The latter flask was cooled in a Dry-Ice-Cellosolve bath. With the reaction flask at room temperature, 1 ml of a solution of 10 mg of sodium metal in dry n-octyl alcohol was added all at once. The gas inlet tube was immediately connected and a slow stream of dry nitrogen was passed through the system. The temperature of the mixture was then raised to 70°C in an oil bath and the C-diazomethane was flushed into the cooled collection flask for about 15 min. A further 1 ml of ether was then added through the gas inlet tube and collection was continued until the distillation of the ether was complete. Use of C-dia-zomethane represents the most general method for the introduction of radioactivity into a haloketone. 

The reagent can be generated in ether solution as required by reaction of the stable precursor N-nitroso-N-benzyl-p-toluenesulfonamide (2) with sodium methoxide. ... 

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