Benzene sulphonyl chloride

The Schotten-Baumann reaction may also be carried out, using, for example, benzene sulphonyl chloride, CeH,SO,Cl (. e., the acid chloride of benzene sulphonic acid, C H5SOjOH) in place of benzoyl chloride, and similar deri a-tives are obtained. Thus when phenol is dissolved in an excess of 10% sodium hydroxide solution, and then shaken with a small excess of benzene sulphonyl... 

Benzene-sulphonylotion. Benzene-sulphonyl chloride, which can be used in place of toluene-/>-sulphonyl chloride, is liquid at room temperature and consequently reacts rapidly when the reaction mixture (as in 3(a)) is vigorously shaken. In general, however, the toluene-/>-sulphonyl derivatives crystallise even more readily than the benzene-sulphonyl analogues, and have lower solubilities and higher m.ps. 

Reduction of a nitro compound to a primary amine. In a 50 ml. round-bottomed or conical flask fitted with a reflux condenser, place 1 g. of the nitro compound and 2 g. of granulated tin. Measure out 10 ml. of concentrated hydrochloric acid and add it in three equal portions to the mixtiue shake thoroughly after each addition. When the vigorous reaction subsides, heat under reflux on a water bath until the nitro compound has completely reacted (20-30 minutes). Shake the reaction mixture from time to time if the nitro compound appears to be very insoluble, add 5 ml. of alcohol. Cool the reaction mixture, and add 20-40 per cent, sodium hydroxide solution imtil the precipitate of tin hydroxide dissolves. Extract the resulting amine from the cooled solution with ether, and remove the ether by distillation. Examine the residue with regard to its solubility in 5 per cent, hydrochloric acid and its reaction with acetyl chloride or benzene-sulphonyl chloride. 

It has been reported that the reaction of 2-(2-pyridyl)indole with benzene-sulphonyl chloride, under phase-transfer catalytic conditions, yields three products, which have been recorded as being the 3-, 4- and 6-benzenesulphonylindoles [56], or 3-chloro-l-benzenesulphonyl-2-(2-pyridyl)indole, as the major product, with the 1-benezenesulphonyl- and l,3-bis(benzenesulphonyl) derivatives, as the minor products [55]. In the light of the earlier discussion, the latter structural assignments appear to be more likely to be correct. 

Method To a solution of (Et0)2P(0)TeNa (5 mmol) in EtOH (10 mL) is added a solntion of benzene sulphonyl chloride (0.88 g, 5 mmol) in THF (10 mL) under N2. An instantaneous reaction occurs and the colour of the mixture changes from colourless to deep black. After stirring for 20 min, a solution of benzyl chloride (0.64 g, 5 mmol) and catalytic amounts of BzEtjN Cr (0.01 g) in THE (10 mL) is added. The mixture is refluxed for 4 h. After evaporating the solvent nnder reduced pressure, the residue is treated with CHCI3 (50 mL). After filtration, the organic phase is evaporated to dryness. The crnde product is recrystallized from EtOH, giving the pure product (1.93 g (82.4%) m.p. 145-147°C). 

SYNS BENZENE SULFONCHLORIDE BENZENESULFONIC (ACID) CHLORIDE BENZENE SULPHONYL CHLORIDE (DOT) BENZENO-SULFO-CHLOREK (POLISH) BENZENOSULPHOCHLORIDE... 

Chhrosidphoitic Acid. Diphenyl chloroarsine, on treatment with chlorosulphonic acid forms, besides benzene sulphonyl chloride, a chloride of diphenyl arsenic acid having the formula (CjH5)2AsOOH.HC1, which forms prisms and melts at 130° C. 

The free and active amino fimction in sulphanilic acid is first protected by acetylation and the resulting -acetamido-benzene sulphonie acid is chlorinated with chlorosulphonic acid to obtain para-acetamido benzene sulphonyl chloride. This on amination with concentrated ammonia solution changes into its corresponding sulphonamide analog, which on hydrolysis results into the formation of sulfanilamide. 

Replacement of the ethyl chlorocarbonate in the foregoing b benzene sulphonyl chloride and carrying out the reaction at 60° C yields benzenesulphonyl-p-aminophenylstibinic acid, CgHg.SO2-XH.CgH4. SbOa-HgO. ... 

Another important aspect of Schotten-Baumann reaction is sulphonylation whereby benzene sulphonyl chloride, CgH SOgCl (i.e., the corresponding acid chloride of benzene sulphonic acid, CgH SOgOH) is employed instead of benzoyl chloride, and almost similar structural analogues may be obtained. 

Explanation. The sulphonylation with phenol takes place in two steps essentially first, is the formation of sodium phenolate by the interaction of phenol with an excess of 10% w v) NaOH solution and secondly, the reaction between sodium phenolate and a small excess of benzene sulphonyl chloride to give rise to the formation of phenyl benzene sulphonate (I). 

Thus, the crystalline ester (I) is separated and the excess of benzene sulphonyl chloride gets hydrolyzed by the alkali producing the soluble sodium benzene sulphonate. 

Sulphonation of hydroxamic acid 120 by a stoichiometric quantity of benzene-sulphonyl chloride in alkaline solution at 25 °C gave imidazolone 117 in 71% yield, but only after recrystallization of intermediate compoimds 121 and 122 from alcohol (68JOC2543). 

Calculated mean amplitudes of vibration (2) for bonds and some rotation-independent non-bond distances of vinyl sulphonyl chloride and benzene sulphonyl chloride... 

Benzene sulphonyl chloride 0 11 30201 The electron diffraction structure analysis utilized vibrational spectroscopic data as much as possible (Brunvoll and Hargittai, 1975) Since this molecule was the first sulphone for which this was done in a more complete way, the procedure is described here in somewhat more detail. 

The rotational forms of benzene sulphonyl chloride considered in this analysis are presented in Figure 23 One of the two symmetrical forms, viz. the one in which the plane of the... 

The molecular model of benzene sulphonyl chloride and the numbering of atoms of the G SO Cl skeleton... 

Newman projections of rotational forms of benzene sulphonyl chloride representing view along the G-S bond and the angles of rotation. The rotation-dependent portions of the radial distributions are shown, E - experimental, and T - theoretical. The parameters used for calculating the theoretical curves are presented in Tables I3, I5 and 17, except for the curve 90 ( ) for which some larger mean amplitudes were used as obtained in the electron diffraction analysis (most notably (C2...C ) =... 

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