- Continuous-Flow Process for the Synthesis of 5-Nitro-1,4-dihydro-1,4-methanonaphthalene
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In this article, we describe a safe and practical process for the synthesis of 5-nitro-1,4-dihydro-1,4-methanonaphthalene (1) via a continuous-flow reactor. The primary procedures in this process involved not merely the production of isoamyl nitrite but also the temperature-programmed Diels-Alder reaction of an aryne (derived from 2-amino-6-nitrobenzoic acid) with cyclopentadiene in the series flow reactor. The continuous-flow process minimized the accumulation of dangerous isoamyl nitrite and the energetic diazonium salt, and the entire reaction time was held down to 250 s.
- Tan, Zhiyong,Li, Zhenhua,Jin, Guoqiang,Yu, Chuanming
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- RETRACTED ARTICLE: Proof of concept efficacy study of intranasal stabilized isoamyl nitrite (SIAN) in rhesus monkeys against acute cyanide poisoning
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Cyanide is a fast-acting toxicant that inhibits aerobic cellular respiration in mitochondria. Historically, amyl nitrite has been used to treat cyanide poisoning. The objective of this study was to demonstrate the effectiveness of intranasal (IN) administration of stabilized isoamyl nitrite (SIAN) against lethal potassium cyanide (KCN) intravenous (IV) challenge in a conscious nonhuman primate (NHP) model. Animals received an IV infusion of a 1 mg/mL KCN solution at a dose of 3.25 mg/kg for 15 min. The IN SIAN treatment was administered at 10 or 12 min post-start of KCN challenge and monkeys were monitored for survival, clinical signs, respiratory and cardiovascular changes via continuous telemetry recording. In addition, blood methemoglobin (metHb) levels and blood gases were closely monitored after KCN administration. Mid to mid-high doses (13.5 or 27.0 μL/kg) of SIAN treatments at 10 min post KCN challenge significantly increased animal survival. Improvements were also observed in respiratory and cardiovascular functions. The benefits of SIAN treatment decreased when treatment was delayed to 12 min post cyanide exposure. IN administration of SIAN 10 min following initiation of a lethal dose KCN infusion produced 100% survival (at doses ≥ 13.5 μL/kg) in NHP model of lethal cyanide intoxication.
- Zhong, Yifei,Raulli, Robert E.,Abtout, Samir,Authier, Simon,Ascah, Alexis,Lambert, Daniel,Gutierrez, Gloria,Cantú, Norma L.,Gutierrez, Nadean,Cabell, Larry,McDonough, Joe,Cakouros, Kelly C.,Gurman, Pablo,Savransky, Vladimir,Barry, John
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- Synthesis, modeling and optimization of cyanide antidote (3-methylbutyl) nitrite using response surface methodology
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In this research, synthesis of cyanide antidote (3-methylbutyl) nitrite has been designed and performed by response surface methodology. The antidote was prepared by the reaction of 3-methyl-1-butanol with sodium nitrite, which is the nitrosonium (NO+) source, in the presence of sulfonic acid-functionalized Fe3O4 (Fe3O4@SO3H) as a nanomagnetic solid acid catalyst and triethylammonium hydrogen sulfate as ionic liquid in aqueous media. Optimization of the reaction conditions was investigated using the response surface method (central composite design). In accordance with analysis of variance, a quadratic polynomial model was able to predict the response. Predicted response values by the obtained model was in good agreement with the experimental results. A clean reaction, easy workup procedure, reusability of the catalyst and a high yield are some advantages of this method.
- Khakyzadeh, Vahid,Vahidian, Hadi Rezaei,Salarian, Amir Ahmad,Zolfigol, Mohammad Ali
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- Method for recycling byproducts in synthesis of diphenyl sulfide compound
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The invention provides a method for recycling byproducts in synthesis of a diphenyl sulfide compound. The byproducts comprise alkyl alcohol and dimethyl disulfide. The method comprises the steps of (1) mixing the byproducts in synthesis of the diphenyl sulfide compound with a sodium nitrite aqueous solution, adding concentrated hydrochloric acid for reaction, and obtaining alkyl nitrite and dimethyl disulfide; and (2) mixing the products obtained in the step (1) with copper powder, adding an aniline compound for reaction, carrying out desolvation treatment on the obtained reaction solution toobtain a diphenyl sulfide compound and byproducts, and returning the byproducts to the step (1). According to the recycling method, the byproducts do not need to be separated, the byproducts serve asraw materials to be directly applied to synthesis of the diphenyl sulfide compound, the process steps are simple and safe, cyclic utilization of the materials is achieved, and the raw material cost ofindustrial production of the diphenyl sulfide compound and the treatment cost of industrial three wastes are remarkably reduced.
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Paragraph 0115-0120
(2021/03/30)
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- Method for synthesizing isoamyl nitrite (by machine translation)
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The method comprises the following steps, mixing: mixture of isoamyl alcohol and solid benzene sulfonic acid resin with a mass ratio :1) of sodium nitrite and isoamyl alcohol: 5555555° C. and carrying out the method according to the present invention to - 555555500° C. and recovering and reusing, the benzene sulfonic acid resin in step, to process industrial waste acid 1) . The reaction solution of Step, is subjected to washing 2) filtration, and stirring reaction, to obtain isoamyl nitrite, with a mass ratio of, The 80% method, disclosed in, is carried out under reduced pressure of 1:1 - 3:1, DEG C. 1:1.35 - 1:1.5. (by machine translation)
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Paragraph 0022-0029
(2020/05/02)
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- Method and device for continuously preparing alkyl nitrite through channelization
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The invention discloses a method and device for continuously preparing alkyl nitrite through channelization. The method comprises the following steps: storing alkyl alcohol and concentrated HCl aqueous solution in a first container and storing sodium nitrite aqueous solution in a second container; continuously conveying the solution in the first container and the second container into a static mixer for mixing by a first metering pump and a second metering pump respectively, enabling mixed solution to continuously enter a tubular reactor for reaction at the temperature of -20 DEG C-5 DEG C for1-250s, enabling feed liquid after reaction to enter a liquid separation tank and performing aftertreatment on the feed liquid in the liquid separation tank, so as to obtain alkyl nitrite. The preparation method disclosed by the invention has the advantages of being good in process safety and easy in control of reaction conditions, achieving continuous production, being high in product yield andachieving large-scale production only through less investment in the industry.
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Paragraph 0031-0034; 0039-0052
(2019/07/04)
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- Synthetic method of isoamyl nitrite
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The invention relates to the technical field of organic chemical synthesis, in particular to a synthetic method of isoamyl nitrite. The synthetic method of the isoamyl nitrite comprises the followingsteps: separately feeding nitric oxide gas and a potassium hydroxide-isoamylol mixed solution into a micro-channel reactor simultaneously; mixing at the temperature of 0-5 DEG C; reacting to generateisoamyl nitrite; collecting a mixture of generated water and the isoamyl nitrite; and washing and distilling under reduced pressure to obtain isoamyl nitrite finished product. The reaction device of the synthetic process requires small space, large-scale production can be realized in a laboratory, the reaction time is short, the capacity is high, the purity of the product is high, the yield is also high, pollution is low, and the safety of the reaction process is high.
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Paragraph 0022-0061
(2019/03/08)
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- Preparation method of furanone acid
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The invention belongs to the technical field of medical chemical industry, and particularly relates to a preparation method of furanone acid. The method comprises the following steps of: adding dropwisely a sodium nitrite aqueous solution into a concentrated sulfuric acid and long-chain alcohol aqueous solution, separating an ester layer to obtain nitrite after the dropwise addition is finished; dissolving 2-acetyl furan in a dilute hydrochloric acid solution, adding concentrated sulfuric acid and a catalyst, controlling temperature, adding dropwisely the nitrite, continuously stirring to react after the dropwise addition is finished, adjusting pH after the reaction is finished, filtering to recover the catalyst, and adding an extracting agent into filtrate to extract long-chain alcohol generated by the reaction and unreacted acetyl furan, wherein a water phase is a furanone acid aqueous solution. By the adoption of the preparation method of the furanone acid, an adopted oxidant only needs to slightly exceed the amount of a substrate, so that generation of toxic gas nitrogen oxide is reduced compared with oxidation of sodium nitrite; and the reaction condition is mild, the use of the catalyst accelerates a hydrolysis process, the side reaction is reduced, the yield is improved and more than 82.5%, and a conversion rate of the 2-acetyl furan reaches more than 95%.
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Paragraph 0058-0060
(2019/07/29)
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- Point of use generation of amyl nitrite
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The present disclosure relates to devices and methods for the preparation of amyl nitrite formulations at a point of use location from relatively shelf-stable reagents employing acidic cationic exchange resins.
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Paragraph 0037-0038
(2015/03/28)
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- ISOAMYL NITRITE FORMULATIONS
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The present invention is directed at isoamyl nitrite formulations suitable for use in medicinal applications. The formulations include a composition of isoamyl nitrite in combination with an epoxidized vegetable oil, identified as stabilized isoamyl nitrite. The isoamyl nitrite may also be combined with petrolatum. Methods of treatment of the formulations are applicable to cyanide poisoning, H2S poisoning as well as treatment for elevated blood pressure.
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Page/Page column 0022
(2015/04/22)
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- Catalyst compositon for olefin polymerization
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The invention relates to a catalyst composition comprising a salt of a non- or weakly coordinating anion, said non- or weakly coordinating anion comprising at least one metal or metalloid ion M with valency v+, v representing an integer between 1 and 5, and at least one bidentate ligand coordinating to this metal or metalloid ion, and a catalyst that can be activated by said non- or weakly coordinating anion, characterized in that said bidentate ligand is a bidentate monoanionic ligand of formula (I): (R1qA1-X-A2R2r), wherein X represents a bridging moiety; A1 and A2 are each independently chosen from the group comprising N, O, P, S, and C; R1 and R2 are each independently chosen from the group comprising an optionally substituted linear or branched (hetero)alkyl group, an optionally substituted (hetero)aryl group, and a Si containing group; and q and r each independently represent an integer with 0≦q, r≦2.
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- Quinuclidine compounds and drugs containing the same as the active ingredient
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The present invention provides an excellent squalene synthesizing enzyme inhibitor. Specifically, it provides a compound (I) represented by the following formula, a salt thereof or a hydrate of them. In which R1 represents (1) hydrogen atom or (2) hydroxyl group; HAr represents an aromatic heterocycle which may be substituted with 1 to 3 groups; Ar represents an optionally substituted aromatic ring; W represents a chain represented by (1) —CH2—CH2— which may be substituted, (2) —CH=CH— which may be substituted, (3) —C≡C—, (4) —NH—CO—, (5) —CO—NH—, (6) —NH—CH2—, (7) —CH2—NH—, (8) —CH2—CO—, (9) —CO—CH2—, (10) —NH—S(O)l—, (11) —S(O)l—NH—, (12) —CH2—S(O)— or (13) —S(O)l—CH2— (l denotes 0, 1 or 2); and X represents a chain represented by (1) a single bond, (2) an optionally substituted C1-6 alkylene chain, (3) an optionally substituted C2-6 alkenylene chain, (4) an optionally substituted C2-6 alkynylene chain, (5) a formula —Q— (wherein Q represents oxygen atom, sulfur atom, CO or N(R2) (wherein R2 represents a C1-6 alkyl group or a C1-6 alkoxy group)), (6) —NH—CO—, (7) —CO—NH—, (8) —NH—CH2—, (9) —CH2—NH—, (10) —CH2—CO—, (11) —CO—CH2—, (12) —NH—S(O)m—, (13) —S(O)m—NH—, (14) —CH2—S(O)m—, (15) —S(O)m—CH2— (wherein m denotes 0, 1 or 2) or (16) —(CH2)n—O— (wherein n denotes an integer from 1 to 6).
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- Method for preparing alkyl nitrites
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The invention concerns a method for preparing alkyl nitrites of formula (I) R ONO (I) ONO wherein R represents a C1-C20, advantageously C2-C10 linear or branched alkyl group. The invention is characterised in that it consists in gradually and continuously adding in an aqueous medium, an alcohol of formula (II) R OH, R being as defined above, a nitrite of formula (III) M NO2, wherein M represents a metal cation, and a strong acid, so as to form continuously said alkyl nitrite, and in continuously drawing off said alkyl nitrite thus formed from the reaction medium.
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- Rates and mechanisms of the thermal solvolytic decomposition of arenediazonium ions
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Arenediazonium tetrafluoroborates have been prepared and the kinetics of solvolysis have been investigated in water, trifluoroethanol, water-trifluoroethanol mixtures, hexafluoropropan-2-ol, trifluoroacetic acid, and ethanol by a UV method. A heterolytic mechanism involving short-lived aryl cations leads to products derived from nucleophilic capture of the aryl cations by solvent or a solute. Ionic solutes in aqueous trifluoroethanol and trifluoromethoxybenzene in trifluoroethanol have no kinetic effect and neither does replacement of the tetrafluoroborate counter-ion by chloride in trifluoroethanol. Rate constants for any one compound are not very solvent dependent, the reactions generally being characterised by high enthalpies of activation and appreciably positive entropies of activation. Compounds with 4-Cl, 4-F, 4-NO2, and 4-MeO substituents proved too unreactive for kinetic studies, but for different reasons. In ethanol, a radical reaction with characteristically different activation parameters competes with the heterolytic path and leads to hydrodediazoniation (reduction) by hydrogen atom abstraction from the CH2 group of ethanol.
- Canning, Peter S. J.,McCrudden, Katharine,Maskill, Howard,Sexton, Brian
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p. 2735 - 2740
(2007/10/03)
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- Inhibitors of platelet aggregation
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Compounds of the formula (I) STR1 wherein B is O or CH2 ; X is selected from NR1 R2, SR1, and C1 -C7 alkyl; Y is selected SR1, NR1 R2, and C1 -C7 alkyl; R1 and R2 is each and independently selected from H, or C1 -C7 alkyl optionally substituted upon or within the alkyl chain by one or more of O, S, N or halogen; R3 and R4 are both H, or R3 and R4 together form a bond; A is COOH, C(O)NH(CH2)p COOH, C(O)N?(CH2)q COOH!2, C(O)NHCH(COOH)(CH2)r COOH, or 5-tetrazolyl, wherein p, q and r is each and independently 1, 2 or 3; as well as pharmaceutically acceptable salts and prodrugs thereof, pharmaceutical compositions comprising the novel compounds and use of the compounds in therapy. Also within the scope of the invention are novel intermediates to the novel compounds. The novel compounds are in particular useful in the prevention of platelet aggregation.
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- Oxidative Cleavage of Ethers by Metallic Nitrates Supported on Silica Gel
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Metallic nitrates supported on silica gel efficiently cleave and oxidize ethers to the corresponding aldehydes or ketones under mild conditions.Silica gel is essential for the efficient oxidation, and Cu(NO3)2 and Zn(NO3)2 are suitable for practical use.Overoxidation of the product aldehydes is not observed.In some cases alkyl nitrites are isolated in addition to the carbonyl compounds, and the decomposition of alkyl nitrites to the corresponding carbonyl compounds is promoted by the presence of metallic nitrates supported on silica gel.Mechanistic study suggests nitrogen dioxide is an active species.
- Nishiguchi, Takeshi,Bougauchi, Masahiro
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p. 5606 - 5609
(2007/10/02)
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- Nitrosation by Alkyl Nitrites. Part 5. Kinetics and Mechanism of Reactions in Acetonitrile
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Simple alcohols and thioglycolic acid react with alkyl nitrites and nitrous acid in acidic acetonitrile solution to give the O- and S-nitrosated products, in reactions which are kinetically zero order in the alcohol or thiol concentration.The results are consistent with rate-liminiting NO+ formation.On addition of the parent alcohol (derived from the alkyl nitrite) reactions are slower and there is a change towards a first order dependence upon the substrate concentration, indicating that under these conditions the reaction of NO+ with the substrate is partly rate limiting.The reactivity order is found to be HNO2 > t-butyl-nitrite > i-propyl nitrite > isopentyl nitrite.Similarly aromatic amines yield nitrosamine or diazonium ion products, but now the kinetics are consistent with rate-limiting attack of NO+ with the unprotonated amine.At higher acidities it is proposed that reaction occurs with the protonated form of the amine.The mechanistic implications of the kinetic results are discussed.
- Crookes, Michael J.,Williams, D. Lyn H.
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p. 1319 - 1322
(2007/10/02)
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