- Scalable electrochemical oxidant-and metal-free dehydrogenative coupling of S-H/N-H
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A practical and scalable electrochemical oxidation of S-H and N-H was developed. This oxidant- and catalyst-free electrochemical process enables S-N bond formation with inexpensive nickel electrodes in an undivided cell. This procedure exhibits broad substrate scopes and good functional-group compatibility. A 50 g scale oxidative coupling augurs well for industrial applications.
- Tang, Shanyu,Liu, Yan,Li, Longjia,Ren, Xuanhe,Li, Jiao,Yang, Guanyu,Li, Heng,Yuan, Bingxin
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Read Online
- Iodine-Mediated Cross-Dehydrogenative Coupling of Heterocyclic Thiols with Amines: An Easy and Practical Formation of S?N Bond
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An efficient iodine-mediated construction of S?N bond was developed. Such a cross-dehydrogenative coupling of heterocyclic thiols with amines proceeded smoothly under metal-free and base-free conditions, and afforded a series of sulfenamides in good to excellent yields. The easily available substrates and convenient synthetic procedure illustrate potential synthetic value of this protocol for the preparation of sulfenamide related biologically or pharmaceutically active compounds.
- Dong, Zhi-Bing,Fan, Yong-Hao,Hao, Er-Jun,Hu, Zhi-Chao,Peng, Kang,Shi, Zhen,Wu, Yue-Xiao
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p. 5889 - 5894
(2021/11/27)
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- Synthetic method for vulcanization accelerator 2-benzothiazolyl-N-morpholinosulfide
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The invention discloses a synthetic method for the vulcanization accelerator 2-benzothiazolyl-N-morpholinosulfide. The synthetic method comprises the following steps: adding 2-thioamino-benzothiazoleand a carbon tetrachloride solution into a reaction vessel, controlling solution temperature, adding a morpholine solution and a potassium sulfate solution, controlling a stirring speed, and carryingout a reaction; and then increasing the temperature, adding potassium ferricyanide powder in batches within 30-50 min, continuing the reaction, lowering the temperature, carrying out washing with a potassium carbonate solution, then carrying out washing with a sodium nitrate solution a plurality of times, carrying out washing with a p-nitrochlorobenzene solution a plurality of times, carrying outrecrystallization in a 1,4-butanediol solution, and then carrying out dehydrating with a dehydrating agent so as to obtain the finished 2-benzothiazolyl-N-morpholinosulfide.
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Paragraph 0017-0028
(2018/07/30)
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- Reusable cobalt-phthalocyanine in water: Efficient catalytic aerobic oxidative coupling of thiols to construct S-N/S-S bonds
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A new aerobic oxidative coupling of thiols in water to construct sulfenamides or disulfides was developed, utilizing cobalt(ii)phthalocyanine-tetra-sodium sulfonate as the catalyst and O2 as the oxidant. The mother liquor could be recycled up to 20 times with negligible loss of activity and only a minor decrease of product yield.
- Dou, Yingchao,Huang, Xin,Wang, Hao,Yang, Liting,Li, Heng,Yuan, Bingxin,Yang, Guanyu
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supporting information
p. 2491 - 2495
(2017/07/17)
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- Preparation method of N-oxydiethylenebenzothiazole-2-sulfenamide
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The invention discloses a preparation method of N-oxydiethylenebenzothiazole-2-sulfenamide in the technical field of chemical synthesis. A chemical equation is shown in the specification, wherein M refers to 2-mercaptobenzothiazole, and NOBS refers to N-oxydiethylenebenzothiazole-2-sulfenamide. The preparation method includes the specific steps of preparing high-concentration sodium hypochlorite bleaching liquor, mother liquor and red oil; sequentially adding the mother liquor, the red oil and morpholine liquid into a hopcalite cartridge, adding the M material with stirring, and conducting temperature rise reaction; extracting oxidization liquid, namely enabling the hopcalite cartridge to stop stirring, extracting 2/3 of oxidization liquid under vacuum, and storing the 2/3 of oxidization liquid as mother liquor for next reaction; conducting alkaline wash and discharging, namely opening the hopcalite cartridge, stirring, performing micro-heating, and adding a 20% sodium chloride solution to subject oxidization materials to alkaline wash; putting alkaline wash materials into a filtering and washing tank, drying by hot air at 50 DEG C after washing and filtration, and packaging so as to obtain the N-oxydiethylenebenzothiazole-2-sulfenamide.
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Paragraph 0013; 0014
(2017/08/28)
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- Electronic Structure and Spectra of Some Benzothiazole-2-Sulfenamide Derivatives
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The electronic structures and spectra of N,N-diethanol-, N-oxadiethylene- and N-benzylbenzothiazole 2-sulfenamide derivatives have been examined both theoretically and experimentally. Equilibrium geometries were determined employing a full geometry optimization using AMI-MO method. The calculated geometric parameters were analyzed in terms of total energy, heat of formation, ionization potential, dipole moments, net charge, bond lengths and bond angles. The electronic absorption spectra were measured in the UV region. The observed spectra consisted of broad envelopes, expectedly composed of overlapping bands. Therefore, Gaussian analysis and MO computations of the spectra were performed as quantitative interpretation of the observed spectra. Analysis of the computed CI states and the MO's involved enabled the assignment of the observed bands. Their origin was assumed as being due to delocalized, localized, or charge transfer transitions. Solvent effects on band position and intensities have also been investigated.
- Moustafa, H.,Abdou, N. Y.,Hamed, M. M.
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p. 309 - 326
(2007/10/03)
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- A convenient synthesis of disulfides and sulfenamides
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We report the synthesis of disulfides from thiols through the use of morpholine-iodine complex.The method is yet another procedure for the preparation of the title compounds.
- Ramadas, Krishnamurthy,Srinivasan, Natarajan
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p. 4179 - 4184
(2007/10/03)
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- Process for the preparation of benzothiazole-2-sulphenamides
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In a process for the production of benzothiazole-2-sulphenamides, a 2-mercaptobenzothiazole in the form of a particulate solid or a dispersion of a particulate solid in a liquid carrier is added gradually and concurrently with an aqueous solution of sodium hypochlorite to a solution of an amine in a mixture of water and a water-miscible organic solvent, the amount of amine being not more than 1.25 moles per mole of 2-mercaptobenzothiazole. A feature of the process is that it represents a significant improvement over prior art methods for the production of sulphenamides derived from secondary amines such as dicyclohexylamine and diisopropylamine.
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- Process for the production of benzothiazole sulphene amides
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Benzothiazole sulphene amides are obtained from dibenzothiazolyl disulphide and water-soluble amines in the absence of an oxidizing agent and in the presence of aqueous alkali in a high yield and with very good stability in storage by placing the amine solution in water and simultaneously adding dibenzothiazolyl disulphide and aqueous alkali from separate storage vessels.
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- ON THE REACTION OF BENZOTHIAZOL-2-YL SULPHENAMIDES WITH PHOSPHITES
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A study of the synthesis of phosphoramidates from phosphites and benzothiazol-2-yl-sulphenamides, indicates that a quinquecovalent phosphorane is an intermediate.Since the initial step in this reaction does not involve attack of phosphorus on nitrogen, it is unlikely that these sulphenamides will act as electrophilic aminating agents towards non-phosphorus nucleophiles.An efficient new method for preparing benzothiazol-2-yl-sulphenamides is reported.
- Brownbridge, P.,Jowett, I. C.
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p. 311 - 318
(2007/10/02)
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- Process for preparing benzothiazolesulphenamides
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Benzothiazolesulphenamides can be prepared in high yield and purity from dibenzothiazolyl disulphide and a primary or secondary amine in the absence of an oxidizing agent in a water-immiscible organic solvent and in the presence of aqueous alkali by presenting a solution of the amine in the organic solvent and adding dibenzothiazolyl disulphide and aqueous alkali either simultaneously or in succession.
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- Process for the production of thiazolyl-2-sulphenamides
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This invention relates to a process for the production of benzothiazolyl sulphenamides corresponding to the following general formula: STR1 in which a corresponding 2-mercaptobenzothiazole or a dibenzothiazolyl-2,2'-disulphide is reacted with a primary or secondary amine at temperatures of from 0 to 100° C. in the presence of ammonia, oxygen, a copper-containing catalyst and a reaction medium containing an excess of the primary or secondary amine or of a mixture of that amine with water and/or a water-miscible organic solvent. Benzothiazolyl sulphenamides are valuable vulcanization accelerators.
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