Carbon Disulfide → HCID 178418395, compound

It must be considered surprising, that nitrosobenzene can be transformed substantially quantitatively to 2-mercaptobenzothiazole with hydrogen sulfide and carbon disulfide. The reaction may be represented by a summation formula, as follows: ##STR1## However, the reaction is in fact much more complicated and is composed of a great number of individual reactions partly taking place concurrently and partly taking place sequentially. At any rate, it can be stated with certainty that an initial quantitative reduction of the nitrosobenzene by hydrogen sulfide to aniline, which then reacts with carbon disulfide to 2-mercaptobenzothiazole in the known manner, is not possible. The main reaction product of nitrosobenzene and hydrogen sulfide is indeed aniline, which is formed with a yield of about 75%, but at least ten more reaction products with aromatic nitrogen groupings are also formed thereby. When this mixture of products is subsequently reacted with carbon disulfide, one nevertheless obtains an almost quantitative--based on the charged nitrosobenzene--yield of 2-mercaptobenzothiazole, thus a much higher yield than would correspond to the aniline content of the reaction mixture. It follows therefore, that, surprisingly, the other reaction products are also transformed into 2-mercaptobenzothiazole. Therefore, when the nitrosobenzene is being reacted with hydrogen sulfide and carbon disulfide at the same time, in keeping with the invention, the reaction will produce the desired 2-mercaptobenzothiazole with high selectivity and yield.

1. customare also formed
2. additionWhen this mixture of products
3. customnevertheless obtains an almost quantitative--

ORD record

ord-6e543e811be541aab7e7cf9e558a3f8b

Source dataset

uspto-grants-1982_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04316031