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United States Atent Thee July 5, 1195 227E254? United States atent thee July 5, 1195 ing at the same time, the evidence for this reaction mech anism is extremely strong and, therefore, although it is 2,712,547 not desired to limit the invention to any particular theory, the evidence is so strong that the mechanism has a high PREPARATION or s-AnYL-TmosULFURIc ACIDS Lil degree of probability. We have determined that the Hans Z. Lecher, Plain?eld, and Elizabeth M. Hardy, second reaction, namely oxidation of the thiol by bisul?de, Bound Brook, N. J., assignors to American Cyanamid actually does take place, The oxidation of thiols is Company, New York, N. ‘L, a corporation of Maine not limited to S-nitro‘oenzene thiol and Z-benzoylarnino No Drawing. Application April 7, 1954, benzene thiol but it may take place with any thiol having Serial No. 421,700 a suf?ciently high oxidation-reduction potential, for ex ample Z-naphthalenethiol and benzenethiol. 11 Claims. (Cl. 26tl-—453) The use of bisul?tes in the reaction of the present invention is a very critical factor. Sulfurous acid will not produce the results of the present invention although This invention relates to an improved process of pre it has been used with aryl-disul?des having basic sub paring salts of certain S-aryl-thiosulfuric acids often re stituents which are, of course, entirely different from ferred to as Bunte salts. More speci?cally it relates to those with which the present invention deals. Sul?tes an improved process of preparing water-soluble salts of are also not useful. It is not known why neither sul S-3-nitrophenyl-thiosulfuric acid and S-Z-benzoylamino furous acid, which does react with basically substituted phenyl-thiosulfuric acid. Salts of the ?rst of the two acids aryl-disul?des, nor why sul?tes do react in the present referred to are of particular interest as they are effective process. It is therefore not intended to limit the inven veterinary agents for the prevention and treatment of tion to any theory of why only bisul?tes may be used. coccidiosis in chickens. The salts can also be hydrolyzed While the use of the bisul?te is an extremely critical factor in the present of mineral acids to 3—nitrobenzene thio and in the present invention the particular bisul?te to be because‘ of the cheapness of the process of the present IO Ll used is not critical, in other words, the cation in the invention this represents an improved method of pro salt makes very little difference. Thus alkali metal bi ducing pure 3-nitrobenzene thiol. sul?tes such as sodium and potassium may be used and A process for the preparation of salts of S-3~nitrophenyl also ammonium bisul?tes and bisul?tes of amines such thiosulfuric acid was developed and is described and as diethylamine, aniline, cyclohexylamine, piperidine, claimed in our copending application Serial No. 355,178, benzylamine, and the like. The preferred bisul?tes are ?led May 14, 1953. This process involved the transfor those of sodium and potassium as they are very e?ective mation of bis-(3-nitrophenyl)-disul?de into the sulfenyl and are cheaper than the other bisul?tes which, while chloride, reaction with an amine to form the sulfenyl operative, present no advantage to offset their higher amide and ?nally reaction with sulfurous acid in alcohol cost. When the preferred solvent, aqueous methanol, is and water. Although this process represented a feasible co Ct used there is a de?nite advantage in using potassium bi commercial process, the number of steps involved kept sulfite in the reaction, with bis-(S-nitrophenyl)~disul?de the cost higher than is desirable. as the potassium salt of the resulting 3-nitrophenyl thio According to the present invention we have found that sulfuric acid has a low solubility in methanol and there the corresponding disulfides can be transformed into salts fore can be readily crystallized in a pure state when the of the S-thiosulfuric acids in a single step process by re 40 hot clari?ed reaction mixture is cooled. The higher sol action with a bisul?te in a solvent mixture containing water ubility of the sodium salt makes its recovery more com and also having a solvent action on the disul?de. For plicated and more than offsets the somewhat lower price practical operation We have found that methanol, ethanol, of sodium bisul?te. or other lower paraf?n alcohols containing water as a It has been pointed out above that sulfurous acid, which minor component constitute the preferred solvent mixture results when sulfur dioxide is used in an aqueous medium, although the invention is not limited thereto and other will not perform the function of the bisul?te in the aqueous mixtures having adequate solubility for the di process of the present invention. However, the presence sul?des may be used. I of free sulfurous acid has no adverse effect provided there The overall reaction of the process of the present m is present a su?icient amount of the bisul?te to carry out vention may be represented as follows: the reaction. As a result it is sometimes advantageous for practical operation to maintain a small excess of free sulfurous acid in the reaction mixture because this insures against the formation of any neutral sul?te and so makes a very careful supervision of the reaction unnecessary. in which equation Ar stands for the aryl residue and Me In contradistinction to the criticality of the bisul?te it for a base cation. While the reaction takes place in a is an advantage that the temperature is not critical. In single step as far as equipment and reaction medium general it should be somewhat elevated as the reaction is concerned, we believe that probably the reaction pro is ‘very slow at room temperature. However, at any tem ceeds in two stages. This mechanism is represented by peratures above 40° C. the reaction proceeds readily the following equations: and no careful control of the temperature is necessary. In practical operation on a large scale, however, it is ad vantageous to permit the aqueous methanol reaction mix ture to boil under a re?ux as this provides automatically a temperature which is within the range of good results. 65 It is a further advantage of the process of the pres It will be seen that the thiol which is produced in the ?rst ent invention that it does not have to be operated in reaction-is reoxidized to the disul?de by more bisul?de, the absence of oxygen or light as neither appears to regenerating half of the amount of disul?de which is affect the reaction adversely and so a simple operating re?ected in the disul?de ?gures in the equation that repre procedure may be used without special precautions. sents the overall reaction. While, as might be expected, 70 The invention will be described in greater detail in it is not possible to obtain completely rigorous proof of conjunction with the following speci?c examples in which the reaction mechanism as the two reactions are proceed the parts are by weight unless otherwise speci?ed. 2,712,547 3 . 4 EXAMPLE 1 The procedure of Example 3 is repeated substituting Potassium salt of S-3-nitr0phenyl-thiosulfuric acid aniline for the methylamine. vThe corresponding aniline salt is obtained but the yield is lower than in Example 3. EXAMPLE 5 a Ammonium salt of S-3-nitr0phenyl-thiosulfuric acid S-SOaNHf N02 Sulfur dioxide is passed into a solution of 3.8 parts of 10 potassium hydroxide in 60 parts of methanol until a slight excess of sulfur dioxide is present. 4.6 parts of NO: bis-(3-nitrophenyl)-disul?de and 5 parts of water are 11 parts of 28.6% aqueous ammonia and 9.24 parts of added. This mixture is re?uxed with agitation until the bis-(3-nitrophenyl)-disul?de are added to 80 parts of reaction is complete. During this time the initial slurry methanol. Sulfur dioxide is passed into the slurry with turns- slightly yellow and a large portion of the solid agitation. An exothermic reaction occurs. Finally the goes intosolution. One part of potassium hydroxide is mixture is re?uxed for a short time, cooled, and ?ltered. added to neutralize the excess bisul?te. The slurry is By evaporation of the ?ltrate the ammonium salt is ob ?ltered hot and the undissolved material is washed with tained in good yield. ' 20 parts of hot methanol. On cooling, the potassium 20 ' salt separates in nice crystals and high yield. It is re- 7 EXAMPLE 6 covered by ?ltration. The potassium salt melts at 195 Sodium salt of S-Z-benzoylaminophenyl-thiosulfuric' acid 198° C. with decomposition. The above procedure is repeated replacing the meth S——SO3Na anol with an equivalent amount of ethanol. The results obtained are substantially the same. NHCOCsH5 EXAMPLE 2 Sodium salt of S-3-nitr0pherzyl-thiosulfuric acid 6.8 parts of bls-(2~benzoylaminophenyl)-disul?de and 5.7 parts of sodium meta-bisul?te are added to 60 parts 30 of methanol and 5 parts of Water. The slurry is re?uxed with agitation until the reaction is ?nished. The hot slurry is ?ltered and the inorganic residue is washed with about 25 parts of hot methanol. By evaporation of, the N02 ?ltrate the desired sodium salt is obtained in excellent (A) U] yield. ‘ ' 5.7 parts of sodium meta-bisul?te and 4.6 parts of EXAMPLE 7 bis-(3-nitrophenyl)-disul?de are slurried in 60 parts of methanol and 5 parts of water.
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