Sulphonated amides

Taurates, methyltaurates and alkyl sulphosuccinamates are hydrolysed by boiling for 6h under pressure at 150-160°C with 6M hydrocholoric acid. 

Taurates and methyl taurates yield fatty acid and the aminosulphonic acid, methyltaurine, with the amino group protonated. 

Alkyl sulphosuccinamates yield a salt of a fatty amine and sulphosuccinic acid. 

Alkali, Amides are resistant to alkaline hydrolysis, but see the comment in section 2.4.4. 

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Benzyl. tblouroDiuffl Mlt M.p. 1 j Sulphonyl chlotide M.p. Sulphon amide M.p. 1 Solphon. anilide M.p. 

Bento amide Benzene- sulphon- amide p-Tolu- enesul- phon- amide Plcrate Formyl Derivative Other Derivatives... 

The imides, primaiy and secondary nitro compounds, oximes and sulphon amides of Solubility Group III are weakly acidic nitrogen compounds they cannot be titrated satisfactorily with a standard alkaU nor do they exhibit the reactions characteristic of phenols. The neutral nitrogen compounds of Solubility Group VII include tertiary nitro compounds amides (simple and substituted) derivatives of aldehydes and ketones (hydrazones, semlcarb-azones, ete.) nitriles nitroso, azo, hydrazo and other Intermediate reduction products of aromatic nitro compounds. All the above nitrogen compounds, and also the sulphonamides of Solubility Group VII, respond, with few exceptions, to the same classification reactions (reduction and hydrolysis) and hence will be considered together. 

Acid Sulphon- amide ArSO,NH, S-Benzyl- Ao-thl- uronium Salt SulphoD- aniUde ArSO,NHPh />-Tolul- dine Salt Sulphonyl Chloride, ArSO,Cl... 

Ether B.P. M.P.. 20 4- 20 "d Sulphon- amide PIcrste Other Derivatives... 

Ureido derivatives of l-alkenyl-3-alkyl-6-aminouracils, such as (LXXI), are reported to have particular activity as appetite inhibitors. They also have anti-secretory, anti-iritic and mild diuretic activities [438]. The related 5-sulphon-amides, such as (LXXII), are said to inhibit the appetite without producing other pharmacological responses such as pressor-depressor, or diuretic effects [439]. 

Amine B.P. M.P. Acetamide Benz- amide Benzene- sulphon- amide p-Tolu- enesul- phon- amlde Benzal Derivative Picrate 3-Nltro- phthal- lmlde 2 4- Dinitro- phenyl Derivative Formyl Derivative Phenyl thio- urea... 

It is generally more convenient to employ the solid toluene-p-sulphonyl chloride (m.p. 69 °C) rather than the liquid benzenesulphonyl chloride. Moreover, the benzenesulphonamides of certain secondary amines are oils or low melting point solids that may be difficult to crystallise the toluene-p-sulphon-amides usually have higher melting points and are more satisfactory as derivatives. ... 

Mixtures of primary, secondary and tertiary amines can usually be separated by Hinsberg s method. This is based on the fact that reaction with benzene-sulphonyl (or toluene-p-sulphonyl) chloride converts primary amines into alkali-soluble sulphonamides, secondary amines into alkali-insoluble sulphon-amides and leaves tertiary amines unaffected. 

Toluene-p- sulphon- amide °C Phenyl- thiourea °C 1-Naphthyl- thiourea °C Picrate °C /V-Substi-tuted phthal-imide °C Benzamide °C Acetamide °C... 

Sulpbonamide M.P. °C N-Xanthyl- sulphon- amide Sulphonamide M.P. °C A -Xanthyl- sulphon- amide... 

Toluene-p- sulphon- amide °C Benzylidene derivative °C Picrate °C 3-Nitro- 2,4-Dinitro- Formyl Phenyl phthalimide phenyl derivative thiourea °C derivative °C °C °C ... 

Radiolabelled derivatives of the herbicide florasulam (N-(2,6-difluo-rophenyl)-5-methoxy-8-fluoro(l,2,4)-triazolo-[l,5-c]-pyrimidine-2-sulphon-amide) (VII) were exposed to natural sunlight in a sterile pH 5 buffer water and in a natural lake water collected from 20 to 30 cm below the surface [70]. The photo degradation was much faster in the natural water system, with a half-life of 3.3 days against 73 days in the buffered aqueous medium. Moreover, the photoproducts produced in the distilled and natural waters were found to be different. Direct photolysis led to the cleavage of the N - S bond with formation of the sulphonic acid derivative (Vila) after 10% of conversion (see Scheme 7). 

Similar mass-spectral rearrangements have been observed in sulphon-amides (66, 67), sulphonimides (68), and phosphine oxides (69, 70). 

Frusonide 2-ammo-4-chloro-baizoicacid-5-sulphon amide 17 red... 

Disposition in the Body. Rapidly and completely absorbed after oral administration. The main metabolic reactions are hydroxyl-ation at the 2- and 3- positions of the propyl substituent in the side-chain, V-dealkylation, and hydrolysis to form the sulphon-amide metabolite. About 80% of a single oral dose is excreted in the urine in 7 days. During chronic therapy, up to 100% of a dose is excreted in the urine in 24 hours, with about 18% of the dose as unchanged drug, 2% as 4-chlorobenzenesulphonamide, 20% as 4-chlorobenzenesulphonylurea, 55% as 2-hydroxychlor-propamide, and 2% as 3-hydroxychlorpropamide. 

Chloro-3,4-dihydro-2//-l,2,4-benzothiadiazine-7-sulphon-amide 1,1-dioxide C7H8C1N304S2 = 297.7 CAS—58-93-5... 

Sulphon Amides.— Just as acetyl chloride is converted into acetamide by the action of ammonia so benzene sulphon chloride yields benzene sulphon amide by the same treatment. 

These two reactions by which a sulphonic acid is converted first into the sulphon chloride and then into the sulphon amide may be applied with considerable ease to all sulphonic acids. The sulphon chloride reacts further with phosphorus penta-chloride all of the sulphur... 

Oral antidiabetes drugs are of two kinds sulphon-amide derivatives (sulphonylureas) and guanidine derivatives (biguanides). They are used by 30% of all diabetics. Unlike insulin they are not essential for life. 

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