40925-65-3

Usage

Chemical Properties

Light yellow solid

InChI:InChI=1/C8H7NO2S/c1-11-5-2-3-6-7(4-5)12-8(10)9-6/h2-4H,1H3,(H,9,10)

Upstream product

• 2182-73-2 6-methoxybenzo[d]thiazole-2(3H)-thione 
• 1747-60-0 6-methoxybenzothiazol-2-ylamine 
• 530-62-1 1,1'-carbonyldiimidazole 
• 6274-29-9 2-amino-5-methoxy-thiophenol 
• 582319-21-9 ethyl (2-iodo-4-methoxyphenyl)carbamate 
• 463-58-1 carbon oxide sulfide 
• 7732-36-7 bis(2-amino-5-methoxyphenyl)disulfide 
• 124-38-9 carbon dioxide 
• 104-94-9 4-methoxy-aniline 

Downstream Products

• 80567-65-3 6-hydroxy-3H-benzothiazol-2-one 
• 105763-66-4 N-cyclohexyl-N-methyl-4-[(2,3-dihydro-2-oxo-2H-1,3-benzothiazol-6-yl)oxy]butyramide 

Relevant academic research and scientific papers

Transition-metal-free synthesis of thiazolidin-2-ones and 1,3-thiazinan-2-ones from arylamines, elemental sulfur and CO2

Transfering waste to treasure is highly important in green chemistry. However, it is difficult to realize it efficiently due to the low reactivity, especially the simultaneous utilization of two unreactive feedstocks in one reaction. Herein, we report the first utilization of both elemental sulfur and CO2 in a multi-component reaction to generate valuable thiazolidin-2-ones and 1,3-thiazinan-2-ones. Under transition-metal-free reaction conditions, a variety of easily available arylamines react with elemental sulfur and CO2 (1 atm) to give functional thiazolidin-2-ones and 1,3-thiazinan-2-ones in moderate to good yields via C-H bond functionalization. This strategy is highlighted by high step economy with generation of three bonds in one reaction and good functional groups tolerance.

Method for synthesizing benzothiazolone-based and 1,3-disubstituted urea-based derivatives through activation of CO2

The present invention relates to a method for synthesizing benzothiazolone-based and 1,3-disubstituted urea-based derivatives through activation of CO2. According to the present invention, an inexpensive and easily-available sulfur-containing metal salt compound is first used as an activation catalyst for CO2, and a reaction raw material and CO2 are converted into a corresponding target compound at a low reaction temperature under a low CO2 pressure; and the method has high atomic economy, can reduce the generation of by-products, meets the standards of environmental friendliness and environmentally friendly chemistry, and is the effective way capable of completely utilizing CO2 as the renewable resource, developing new energy and achieving the beneficial cycle of carbon in nature.

Efficient Synthesis of Benzothiazolone Derivatives by a Domino Reaction of Disulfide and COS under Mild Conditions

Carbonyl sulfide (COS), whose molecular structure is similar to CO2 and CS2, could be used as a better alternative carbonyl reagent due to its high chemical activity. However, the unfriendly by-product H2S would be generated when COS is used as a carbonyl reagent in the carbonylation reaction. In this report, the odorless and stable disulfide was used to replace the traditional foul smelling and unstable o-aminobenzenethiol to react with COS for preparing benzothiazolone derivatives in excellent yield, in which coupling reaction of H2S generation and S–S bond cleavage was firstly designed. Notably, the C=O of COS was converted into benzothiazolone derivatives by carbonylation reaction and the sulfur of COS was transformed into sulfur and sulfide after cleaving the S–S bond by a domino reaction of disulfide and COS under mild conditions. This efficient synthetic methodology provided a promising process for the utilization of COS.

Method for synthesizing benzothiazole-2-ketone derivative from carbonyl sulfide and disulfide as raw materials

The invention discloses a method for synthesizing a benzothiazole-2-ketone derivative from carbonyl sulfide and disulfide as raw materials. The method comprises the following steps: mixing disulfide,inorganic sulfide and an organic solvent, introducing sufficient COS to implement a reaction, and concentrating and purifying a reaction liquid, thereby obtaining the benzothiazole-2-ketone derivative. The inorganic sulfide used in the method is adopted as an activation catalyst and is low in price and easy to obtain; a catalysis system is relatively simple, and no other catalyst promoter is addedexcept reactants and inorganic sulfide; direct dehydration is implemented in the reaction process, no other dehydration agent is used, and thus the atom economy is improved; the catalysis system is good in applicability, is applicable to synthesis of fine chemicals with high additional values, and is very good in substrate applicability to each fine chemical with high additional values; reactionsare implemented at normal temperatures, normal pressure or low pressure, and thus danger coefficients can be reduced; the reaction time is short, and the efficiency can be improved.

CuI-catalyzed one-pot synthesis of benzothiazolones from 2-iodoanilines-derived carbamates and sodium sulfide

A copper-catalyzed procedure was developed for assembling benzothiazolones from ethyl 2-iodophenylcarbamates and sodium sulfide. A number of functional groups, such as methoxy, acyl, amide, carboxylate, trifluoromethyl, fluoro, and chloro, were tolerated under these conditions, providing benzothiazolones in good yields.

Inhibitors of cyclic AMP phosphodiesterase. 1. Analogues of cilostamide and anagrelide

Evaluation of a series of lactam heterocyclic analogues of cilostamide as inhibitors of cyclic AMP phosphodiesterase derived from both human platelets and rat heart in comparison with their corresponding methoxy-substituted heterocycles has revealed that the N-cyclohexyl-N-methyl-4-oxybutyramide side chain of 2 is an important lipophilic and/or steric pharmacophore. Attachment of this side chain to the parent heterocycle of the potent cyclic AMP phosphodiesterase inhibitor anagrelide afforded the hybrid structure RS-82856, shown to be more potent than either of its progenitors as an inhibitor of cyclic AMP phosphodiesterase or of ADP-induced platelet aggregation. The available in vitro data suggest that 1 possesses potentially useful antithrombotic and cardiotonic properties.

Suppressing pain with benzothiazol-2(3H)-ones

There are described pharmaceutical compositions containing as active substances benzothiazol-2(3H)-ones of the general formula STR1 wherein R represents a hydrogen atom or a methyl, methoxy, or ethoxy group. The pharmaceutical compositions serve as analgesics and antipyretics and possess little or no methemoglobin-forming activity.