112006-75-4

Basic information

• Product Name: 3-Pyridinecarboxamide,2-(aminosulfonyl)-N,N-dimethyl-
• Synonyms: N,N-Dimethylnicotinamide-2-sulfonamide;2-(Aminosulfonyl)-N,N-dimethyl-3-pyridinecarboxamide
• CAS NO: 112006-75-4
• Molecular Formula: C₈H₁₁N₃O₃S
• Molecular Weight: 229.2562
• EINECS: 413-440-7
• Product Categories: Amines;Pyridines
• Mol File: 112006-75-4.mol

Chemical Properties

• Melting Point: 198-209 °C (decomp)
• Boiling Point: 488.9 °C at 760 mmHg
• Flash Point: 249.5 °C
• Appearance: /
• Density: 1.373 g/cm³
• Vapor Pressure: 1.04E-09mmHg at 25°C
• Refractive Index: 1.571
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Solubility: Acetonitrile (Slightly), DMSO (Slightly), Methanol (Slightly)
• PKA: 8.81±0.60(Predicted)
• CAS DataBase Reference: 3-Pyridinecarboxamide,2-(aminosulfonyl)-N,N-dimethyl-(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Pyridinecarboxamide,2-(aminosulfonyl)-N,N-dimethyl-(112006-75-4)
• EPA Substance Registry System: 3-Pyridinecarboxamide,2-(aminosulfonyl)-N,N-dimethyl-(112006-75-4)

Safety Data

• Hazard Codes: Xi
• Statements: 43-52/53
• Safety Statements: 24-37-61-24/25
• Hazardous Substances Data: 112006-75-4(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
3-Pyridinecarboxamide,2-(aminosulfonyl)-N,N-dimethylis used as a key intermediate in the synthesis of various organic compounds. Its versatile chemical properties allow it to be employed in the creation of a wide range of products, from pharmaceuticals to agrochemicals.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 3-Pyridinecarboxamide,2-(aminosulfonyl)-N,N-dimethylis used as a building block for the development of new drugs. Its unique structure and reactivity make it a promising candidate for the synthesis of novel therapeutic agents with potential applications in treating various diseases and medical conditions.
Used in Agrochemical Industry:
3-Pyridinecarboxamide,2-(aminosulfonyl)-N,N-dimethylis also utilized in the agrochemical industry for the synthesis of new pesticides and other crop protection agents. Its chemical properties enable the development of innovative products that can help improve crop yield and protect plants from various pests and diseases.
Used in Dye and Pigment Industry:
In the dye and pigment industry, 3-Pyridinecarboxamide,2-(aminosulfonyl)-N,N-dimethylis used as a starting material for the production of various dyes and pigments. Its light yellow color and chemical properties make it suitable for the development of new colorants with improved performance and stability.
Used in Research and Development:
3-Pyridinecarboxamide,2-(aminosulfonyl)-N,N-dimethylis also used in research and development laboratories for the exploration of new chemical reactions and the synthesis of novel compounds. Its unique properties make it an interesting subject for scientific investigation and the potential discovery of new applications and uses.

InChI:InChI=1/C8H11N3O3S/c1-11(2)8(12)6-4-3-5-10-7(6)15(9,13)14/h3-5H,1-2H3,(H2,9,13,14)

Upstream product

• 1336-21-6 ammonium hydroxide 
• 112006-57-2 N,N-dimethyl-2-(phenylmethylthio)-3-pyridinecarboxamide 
• 112006-58-3 2-sulfonyl chloride-N,N-dimethylnicotinamide 
• 124-40-3 dimethyl amine 
• 100-54-9 pyridine-3-carbonitrile 
• 14906-64-0 3-cyanopyridine N-oxide 
• 111991-09-4 nicosulfuron 
• 178613-27-9 ethyl 2-mercaptonicotinate 
• 121050-19-9 2-mercapto-N,N-dimethylnicotinamide 
• 52943-21-2 2-chloropyridine-3-carboxylic acid N,N-dimethylamide 
• 2942-59-8 2-chloronicotinic acid 

Downstream Products

• 138417-40-0 2-sulfo-nicotinic acid imide 
• 111991-09-4 nicosulfuron 

Relevant articles and documents

Preparation method of 2-aminosulfonyl-N, N-dimethyl nicotinamide

The invention provides a preparation method of 2-aminosulfonyl-N, N-dimethyl nicotinamide. The preparation method comprises the following steps: synthesizing 2-chlorine-N, N-dimethyl nicotinamide by taking 2-cyano-5-dimethylamino-2, 4-pentadienyl dicarboxamide and hydrochloric acid gas as raw materials, and reacting at the temperature of between 0 and 100 DEG C to synthesize the 2-chloro-N, N-dimethyl nicotinamide. Furthermore, the preparation method provided by the invention also comprises the step of sequentially synthesizing the 2-sulfydryl-N, N-dimethyl nicotinamide, the 2-chlorosulfonyl-N, N-dimethyl nicotinamide and the 2-aminosulfonyl-N, N-dimethyl nicotinamide by taking the 2-chloro-N, N-dimethyl nicotinamide as a raw material. According to the preparation method of the 2-aminosulfonyl-N, N-dimethyl nicotinamide, provided by the invention, the novel preparation method is provided by taking the 2-cyano-5-dimethylamino-2, 4-pentadiene dicarboxamide as an initial raw material, and the preparation method is relatively short in synthetic route, relatively high in yield and relatively low in cost.

Method for closed-loop synthesis of nicosulfuron by using hydrogen sulfide

The invention belongs to the technical field of nicosulfuron original medicine production, and particularly relates to a method for closed-loop synthesis of nicosulfuron by using hydrogen sulfide, wherein the method comprises the following steps: reacting tetramethoxypropane with ethyl cyanoacetate to generate 1-cyano-4-methoxy-1-ethoxycarbonyl-1,3-butadiene (cyanoene for short, the same below); reacting cyano alkene with hydrogen sulfide to generate ethyl 2-mercaptonicotinate (sulfydryl substance for short) in a closed-loop manner; reacting the sulfydryl substance with dimethylamine, and then carrying out oxychlorination reaction to obtain sulfonyl chloride; carrying out ammonolysis reaction on the sulfonyl chloride and ammonia gas to obtain sulfonamide; and reacting sulfonamide with solid light and pyrilamine to obtain the nicosulfuron. According to the method for closed-loop synthesis of nicosulfuron by using hydrogen sulfide, each reaction step is mild and controllable, process equipment is simple, the production cost is low, the product quality is good, three wastes are reduced, energy is saved, the production environment is improved, and the goal of carbon neutralization is favorably realized.

Preparation method of nicosulfamide

The invention relates to the technical field of pesticide synthesis, in particular to a preparation method of nicosulfamide. The preparation method of the smoke sulfonamide comprises the following steps: taking 3-cyanopyridine as a raw material, and carrying out oxidation reaction to obtain 3-cyanopyridine nitric oxide; carrying out sulfonation reaction and ammoniation reaction on the 3-cyanopyridine nitrogen oxide to obtain 2-sulfonamido-3-cyanopyridine; carrying out alkaline hydrolysis on the 2-sulfamido-3-cyanopyridine to obtain 2-sulfamido nicotinic acid; and carrying out amidation reaction on the nicotinic acid 2-sulfonamide to obtain the nicotinamide. The preparation method of the nicosulfamide is simple to operate and low in raw material cost, by-products generated in the preparation process can be recycled, the cost is saved, and the prepared nicosulfamide is high in yield and purity.

Preparation method of nicosulfuron crude drug

The preparation method, of the nicosulfuron crude drug comprises the following steps: synthesizing, isocyanate group sulfonyl - NNNN, N-dimethyl nicotinamide: triphosgene 2 - triethylamine and 2 - amino - 4444, 6-dimethoxypyrimidine as main raw materials in, reaction to synthesize nicosulfuron-N, N-dimethylnicotinamide 0-80 °C and 2 - amino - 4444, 6-dimethoxypyrimidine as main raw materials to synthesize nicosulfuron-N, N-dimethylaminopyridine as a main, raw material, and high yield; of nicosulfuron. 2 - The method provided by the invention comprises the following steps, synthesizing 2 - 2 -isocyanuric acid group, sulfonyl - NNNNor N-dimethylaminopyrimidinil in 0-100 °C reaction to form a nicosulfuron prodrug. by reacting. 2 - The preparation method comprises the following. steps, synthesizing nicosulfuron-N, N-dimethyl nicotinamide.

Synthesis method of 2-aminosulfonyl-N, N-dimethyl nicotinamide

The invention belongs to the field of pesticides, relates to a synthesis technology of a nicosulfuron intermediate, in particular to a synthesis method of 2-aminosulfonyl-N, N-dimethyl nicotinamide. According to the method, 2-chloro-N, N-dimethyl nicotinamide and sodium thiosulfate are used as raw materials, the method comprises the processes of sulfhydrylation, sulfonation, ammoniation reaction and the like, the reaction process is few in by-product, high in yield and low in raw material cost, hydrogen sulfide is removed from the source of the reaction, real clean production is achieved, andthe product content and yield are increased.

Preparation method of nicosulfuron

The invention discloses a preparation method of nicosulfuron. The method comprises the following steps: carrying out first reaction treatment on 2-sulfamoyl-N,N-dimethylformamide to obtain corresponding carbamate, and carrying out a second reaction on the carbamate and dimethoxyaminopyrimidine to obtain the nicosulfuron. On the basis of the prior art, by improving the technological process, the yield of the intermediate 2-sulfamoyl-N,N-dimethylnicotinamide is increased, that is, the yield of nicosulfuron can be effectively increased; and meanwhile, the adopted raw material 2-chloro-N,N-dimethylnicotinamide can effectively reduce the cost so as to meet the requirements of modern industrial production.

Synthesis process of nicosulfuron original medicine

The invention relates to a synthesis process of a nicosulfuron original medicine. In the method, 2-chloronicotinic acid is used as a raw material to synthesize an intermediate 2-sulfunylchloro-N,N-dimethyl nicotinamide, which is then reacted with amino pyrimidine to produce the nicosulfuron. The method has good atom economy and meanwhile avoids use of highly-toxic raw materials, such as phosgene, and expensive catalysts. The method has simple operations, is low in pollution and is low in cost; by means of continuous material feeding and continuous distillation, continuous synthesis of the nicosulfuron original medicine is achieved, and synthesis quality and yield of the nicosulfuron are greatly improved.

Preparation method of 2-aminosulfonyl-N,N-dimethylnicotinamide

The invention provides a preparation method of 2-aminosulfonyl-N,N-dimethylnicotinamide. With 2-aminonicotinic acid serving as the raw material, 2-aminosulfonyl-N,N-dimethylnicotinamide is prepared through the first step of conducting a chloroformylation reaction and an amination reaction, the second step of conducting a diazotization reaction, the third step of conducting a Sandmeyer reaction and the fourth step of conducting an amination reaction. The preparation method has the advantages that reaction conditions are mild, stable and controllable, side reactions are not likely to occur as the number of active sites is small, and the whole route is high in yield and quality; cost can be effectively reduced as original materials can be easily obtained from the market, and the preparation method is environmentally friendly as no polysulfide is used.

Nicosulfuron: Alcoholysis, chemical hydrolysis, and degradation on various minerals

Alcoholysis (methanol or ethanol) and hydrolysis (pH ranging from 4 to 11) of the herbicide nicosulfuron at 30 °C principally involves the breakdown of the urea part of the molecule. A high yield of the corresponding carbarnate was obtained along with aminopyrimidine during alcoholysis. Hydrolysis led to both aminopyrimidine and pyridylsulfonamide. The latter compound may be easily cyclized (pH ≥ 7). First-order kinetics describe the rates of alcoholysis and hydrolysis well. The rate constants (0.44 days-1 for methanolysis) decreased from 0.50 to 0.002 days-1 as pH increased from 4 to 8, then remained stable under alkaline conditions. In acidic or neutral solution, the hydrolysis path appeared prevalent (≥70%), whereas in an alkaline medium it decreased when pH increased. The chemical degradation of nicosulfuron on various dry minerals (calcium bentonite, kaolinite, silica gel, H+ bentonite, montmorillonite K10, and alumina) was investigated at 30 °C. The best conditions for the degradation are obtained on acidic minerals after herbicide deposition using the liquid method. Under these conditions an acceptable correlation with pseudo-first-order kinetics was observed, and the major degradation path is similar to that proposed for chemical hydrolysis. Conversely, alumina seemed to favor other unknown degradation processes. The hydrolysis paths of nicosulfuron and rimsulfuron appeared to be different.

Mercapto-substituted pyridine compounds, aminocarbonyl-substituted pyridinesulfinic acid compounds and process for preparing the same

An aminocarbonyl-substituted pyridinesulfinic acid intermediate for production of an herbicide having formula (V): STR1 wherein R3 and R4 are selected from the group consisting of hydrogen and alkyl groups, or a salt thereof. The aminocarbonyl-substituted pyridinesulfinic acid or salt thereof is useful as the precursor of aminosulfonyl-substituted pyridinecarbonic acid amide, which in turn is useful as the starting material for agricultural chemicals, medicine, etc.