O-Toluenesulfonamide

Directed ortV o-methyl lithiation/cyclization of AT-acyl-o-toluenesulfonamides 229 provides a second approach to the synthesis of 1,2-benzothiazine 1,1-dioxides 230 via creation of the bond between C-3 and C-4 (Scheme 31) <1999CPB1730>. The best yields of cyclization products are achieved when the R group on the amide 229 is bulky. In the case of substrates with small R groups (Me, Ph, etc.), products 231 and 232 are formed from attack of the Bu"Li on the carbonyl carbon. 

Saccharin in high yield may be obtained by oxidising o-toluenesulfonamide with dichromate and sulfuric acid. 

Chemical Name (+/-)-5-(l-Hydroxy-2-((2-(o-methoxyphenoxy)ethyl)amino) ethyl)-o-toluenesulfonamide monohydrochloride... 

The use of a mercury lamp instead of a tungsten source for DAIB-I2 oxidations of TV-alkyl-o-toluenesulfonamides affords mixtures of saccharins and their sulfoxamide analogs (99TL14885). The efficiency of sulfoxamide formation depends on the nature of the TV-alkyl group and was demonstrated primarily with A-ethyl analogs of 185. 

Stock Standard Preparation Transfer 20.0 mg each of reagent-grade o-toluenesulfonamide and p-toluenesulfon-amide into a 10-mL volumetric flask, dissolve in and dilute to volume with methylene chloride, and mix. 

Maintain the column at 180°. Set the injection port temperature to 225° and the detector to 250°. Use helium as the carrier gas with a flow rate of 30 mL/min. Adjust the instmment attenuation setting so that 2.5 jxL of the Diluted Standard Preparation containing 200 (xg/mL of each toluenesulfonamide gives a response of 40% to 80% of full-scale deflection. Record the chromatogram, note the peaks for o-toluenesulfon-amide, p-toluenesulfonamide, and the n-tricosane internal standard, and calculate the areas for each peak by suitable means. The retention times for o-toluenesulfonamide, p-toluenesulfonamide, and n-tricosane are about 5, 6, and 15 min, respectively. 

C7H9N02S o-toluenesulfonamide 88-19-7 25.00 1.2247 2 11286 C7H11N02 trans-2-amino-4-cyclohexene-1 -carboxylic acid 97945-19-2 23.75 1.0648 2... 

Pure or alloyed lead may be employed as anode in sulfuric acid addition of 1% silver, 0.3% tin, and a little cobalt raises its resistance toward corrosion. Other metals may improve the yield of a given electrode process. Thus, addition of antimony and cadmium to a lead anode [152] is advantageous in the oxidation of o-toluenesulfonamide to o-benzoylsulfonimide (saccharin). The same effect may be obtained, however, by using an uncoated, unalloyed lead anode if Sb203 is added to the anolyte [153]. It seems possible that the dissolution of some antimony from the alloyed lead anode takes place and produces the same effect as the Sb203 in the anolyte. 

Oxidation of the methyl group in o-toluenesulfonamide at a nickel oxide electrode in aqueous carbonate leads to saccharin in 40% yield [68]. 

DeGarmo O, Ashworth GW, Eaker CM, Munch RH. Hydrolytic stability of saccharin. Am Pharm Assoc (Sci) 1952 41 17-18. Arnold DL, Moodie CA, Grice HC, et al. Long-term toxicity of ortI o-toluenesulfonamide and sodium saccharin in the rat. Toxicol Appl Pharmacol 1980 52 113-152. 

Several synthetic approaches to the l,2-benzothiazin-3-ones have been described. Usually, an ortho-substituted sulfonamide was cyclized to form the thiazine ring. For example, Lombardino and Wiseman14,38 treated /V-methyl-o-toluenesulfonamide (45) with butyllithium the dianion with CO 2 produced o-sulfamoylphenylacetic acid 46 which was cyclodehydrated to 3,4-dihydro-2-alkyl-l,2-benzothiazin-3(2H)-one 1,1-dioxide (47) in good yield (Eq. 10). This same reaction sequence was applied to analogs of 47 such as the 7-methyl, the 7-chloro, and the 2-benzyl derivatives.38... 

Benzenesulfbnamide, N-ethyl-2-methyl- EINECS 214-073-3 N-Ethyl-o-toluenesulfonamide N-Ethyltoluene-2-sulphonamide HSDB 5782 o-Toluenesulfonamide, N-ethyl- Uniplex 108. Plasticizer for nylon, shellac, cellulose acetate, protein materials, PVAc adhesives, and nitrxellulose lacquers. Un/tex. 

Sulfo and nitro substituents also often make it harder to degrade the side chain. For the preparation of nitrobenzoic acids from nitrotoluenes a dichromate-sulfuric acid mixture is superior to chromic acid alone in glacial acetic acid trinitrotoluene is converted into trinitrobenzoic acid by the former but is not attacked by the latter reagent. o-Toluenesulfonamide (obtained from the acid by way of the chloride) is oxidized by alkaline permanganate solution... 

Controlled potential oxidation of o-toluenesulfonamides (180) at a platinum anode in acetonitrile using a divid cell provided 4,5-dihydro-l,2,4-benzothiadiazepine 1,1-dioxides (182) in generally good yields via (181) (Scheme 33). The scope and limitation of this one-step heterocyclization... 

Among other plasticizers, o- and p-toluene-sulfonamides are used to improve the processibility of urea and melamine resins, and cellulose-based adhesives. For the same reason, N-ethyl-o-toluenesulfonamide and N-ethyl-p-toluenesulfonamide are used for polyamides, casein, and zein. 

Methyl benzenemethanol. SeeCresyl alcohol a-Methylbenzenemethanol acetate. Seea-M ethyl benzyl acetate 2-Methylbenzenesulfonamide. See o-Toluenesulfonamide 4-Methylbenzenesulfonamide. See p-Toluenesulfonamide o-Methylbenzenesulfonamide. See o-Toluenesulfonamide p-Methylbenzenesulfonamide. See p-Toluenesulfonamide 4-Methylbenzenesulfonic acid p-Methylbenzenesulfonic acid. See p-Toluene sulfonic acid... 

Oxytetrin. See Oxytetracycline hydrochloride Oxythioquinox. See Chinomethionat Oxytol acetate. See Ethoxyethanol acetate Oxytoluene. See Cresylic acid m-Oxytoluene. Seem-Cresol o-Oxytoluene. Seeo-Cresol p-Oxytoluene. See p-Cresol Oxyurea. See Hydroxyurea o-Toluenesulfonamide... 

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