- Preparation method of O-methylbenzoyl nitrile
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The method comprises the following steps: firstly dissolving o-methylbenzoic acid in a toluene solvent, dropping the dimethyl sulfoxide to carry out reaction, and removing a small amount of unreacted dichlorosulphoxide at low temperature after the reactio
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Paragraph 0054; 0057-0060; 0063-0066; 0069-0072; 0075-0078;
(2021/11/21)
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- Novel synthesis method of alpha-carbonyl acid ester
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The invention discloses a novel synthesis method of alpha-carbonyl acid ester. The method comprises the following steps: carrying out chlorination reaction on an alpha-methylene-containing nitrile compound and chlorine to obtain dichloronitrile, reacting the dichloronitrile product in a sulfuric acid and water system to obtain formyl cyanide, then acquiring an imino sulfate compound in the same reaction system, and finally performing esterification to obtain the target product. The adopted reaction raw materials are wide in sources and low in price, highly toxic solid sodium cyanide can be prevented from being used in the prior art, the method is environmentally friendly, and the method is easy to operate, mild in condition and easy to industrialize.
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Paragraph 0016; 0044; 0047
(2020/07/21)
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- A stretching of the intermediate O-methyl benzoyl nitrile synthetic method
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The invention relates to a method for preparing a key intermediate methylbenzoyl cyanide in the process of synthesizing trifloxystrobin. The method comprises the following steps: adding o-toluoyl chloride, a solvent and a catalyst into a reaction kettle; introducing metered hydrocyanic acid gas, completely reacting under a heat insulating conditon to obtain methylbenzoyl cyanide, and carrying out back-distillation to obtain a methylbenzoyl cyanide product. The content of methylbenzoyl cyanide is over 99 percent and the yield can be over 95 percent metered in form of o-toluoyl chloride. The method is simple and convenient to operate, the utilization of the raw material o-toluoyl chloride is high; except the byproduct hydrochloric acid, almost no other wastes are generated, and atomic economic reaction is basically realized. The method is a synthesizing process with good economic prospect.
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Paragraph 0030; 0031; 0032; 0033; 0034; 0035; 0036-0041
(2017/03/22)
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- Acceptorless and Base-free Dehydrogenation of Cyanohydrin with (η6-Arene)halide(Bidentate Phosphine)ruthenium(II) Complex
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Ruthenium-catalyzed dehydrogenation of cyanohydrins under acceptorless and base-free conditions was demonstrated for the first time in the synthesis of acyl cyanide. As opposed to the thermodynamically preferred elimination of hydrogen cyanide, the dehydrogenation of cyanohydrins could be kinetically controlled with ruthenium (II) bidentate phosphine complexes. The effects of the arene, phosphine ligands and counter anions were investigated in regard to catalytic activity and selectivity. Selective dehydrogenation can occur via β-hydride elimination with the experimentally observed [(alkoxide)Ru] complex. (Figure presented.).
- Kim, Kicheol,Moeljadi, Adhitya Mangala Putra,Hirao, Hajime,Hong, Soon Hyeok
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supporting information
p. 3292 - 3298
(2017/09/06)
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- Rh-Catalyzed Asymmetric Hydrogenation of 1,2-Dicyanoalkenes
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A highly efficient enantioselective hydrogenation of 1,2-dicyanoalkenes catalyzed by the complex of rhodium and f-spiroPhos has been developed. A series of 1,2-dicyanoalkenes were successfully hydrogenated to the corresponding chiral 1,2-dicyanoalkanes under mild conditions with excellent enantioselectivities (up to 98% ee). This methodology provides efficient access to the asymmetric synthesis of chiral diamines.
- Li, Meina,Kong, Duanyang,Zi, Guofu,Hou, Guohua
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p. 680 - 687
(2017/04/26)
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- Synthesis and biological evaluation of kresoxim-methyl analogues as novel inhibitors of hypoxia-inducible factor (HIF)-1 accumulation in cancer cells
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We designed and synthesized strobilurin analogues as hypoxia-inducible factor (HIF) inhibitors based on the molecular structure of kresoxim-methyl. Biological evaluation in human colorectal cancer HCT116 cells showed that most of the synthesized kresoxim-methyl analogues possessed moderate to potent inhibitory activity against hypoxia-induced HIF-1 transcriptional activation. Three candidates, compounds 11b, 11c, and 11d were identified as potent inhibitors against HIF-1 activation with IC50 values of 0.60–0.94?μM. Under hypoxic condition, compounds 11b, 11c, and 11d increased the intracellular oxygen contents, thereby attenuating the hypoxia-induced accumulation of HIF-1α protein.
- Lee, Sanghyuck,Kwon, Oh Seok,Lee, Chang-Soo,Won, Misun,Ban, Hyun Seung,Ra, Choon Sup
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p. 3026 - 3029
(2017/05/31)
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- AN IMPROVED PROCESS FOR THE SYNTHESIS OF STROBILURIN FUNGICIDES VIZ TRIFLOXYSTROBIN AND KRESOXIM-METHYL
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The present invention relates to an improved process for the synthesis of E-isomer of compound of formula (5). It further relates to the conversion of formula (5), wherein R is H, to Intermediate (I) and subsequently to substantially pure Trifloxystrobin, compound of formula (I) in good yield.
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Page/Page column 28; 30
(2013/10/21)
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- METHOXYIMINO COMPOUNDS AND FUNGICIDE COMPOSITION COMPRISING SAME
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The present invention provides a methoxyimino compound, and a fungicide composition comprising same as an active ingredient. The methoxyimino compound of the present invention, which has an excellent antifungal activity against a wide spectrum of fungi even at a low application rate, can be used to protect various crops.
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Page/Page column 15
(2009/07/17)
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- A new convenient synthesis of aroyl cyanides via the formation of cyanohydrin nitrate intermediates
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The treatment of α-bromoarylacetonitriles with AgNO3 generates cyanohydrin nitrate intermediates, which easily eliminate nitrous acid with the formation of carbonyl bond to afford aroyl cyanides in good to high yields.
- Sueda, Takuya,Shoji, Masashi,Nishide, Kiyoharu
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p. 5070 - 5072
(2008/12/21)
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- AgI-PEG400-KI catalyzed environmentally benign synthesis of aroyl cyanides using potassium hexacyanoferrate(II) as the cyanating agent
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A practical cyanation of aroyl chlorides with 0.2 equivalent of non-toxic cyanide source, K4[Fe(CN)6], 3 mol% AgI, 4 mol% PEG-400, and 3 mol% KI as the catalyst system is described. The reactions were performed in DMF at room temperature and provided the corresponding aroyl cyanides in 64-89% yield, typically in less than ten hours. Georg Thieme Verlag Stuttgart.
- Li, Zheng,Shi, Shengyi,Yang, Jingya
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p. 2495 - 2497
(2008/02/11)
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- A novel heterogeneous synthesis of acyl cyanides catalyzed by PEG400 and zinc iodide
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Aroyl cyanides were readily synthesized in moderate yields by the cyanation of aroyl chlorides with dry powdered potassium cyanide under the catalysis of PEG400 and zinc iodide in dichloromethane at room temperature. A preliminary study on the one-pot preparation of acetyl cyanide was also reported.
- Cao, Yu-Qing,Du, Yun-Fei,Chen, Bao-Hua,Li, Ji-Tai
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p. 2951 - 2957
(2007/10/03)
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- Acyl cyanides as carbonyl heterodienophiles: Application to the synthesis off naphthols, isoquinolones, and isocoumarins
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Irradiation of 2-methylbenzoyl cyanide (3a) in acetonitrile solution results in the formation of its dimer, which upon loss of HCN gives rise to the cycloadduct 7a. The dimerization also proceeds efficiently with derivatives of 3a giving adducts 7b and 7c
- Connors, Richard
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p. 221 - 226
(2007/10/03)
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- Acrylate fungicides
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Compounds of formula I STR1 wherein X is oxygen or sulphur, W is CH or N, m is 0 or 1, and either a) n is 1 and Q is a non-aromatic heterocyclic ring of 3 to 10 ring atoms, containing one to three hetero atoms selected from oxygen, sulphur and nitrogen, which may be substituted and may be fused to another ring, with the proviso a) that if Q is thiazol-2-in-2-yl, it is substituted but not by methylene, and b) Q is not a six membered ring containing only two nitrogen atoms, or b) n is 0 or 1 and STR2 where R1 is alkyl, alkoxy or alkylthio, and R2 is heteroaryl, non aromatic heterocyclyl, optionally substituted cycloalkyl or optionally substituted alkyl containing at least 5 carbon atoms, phenyl substituted by one or more groups selected from halogen, optionally substituted alkyl, alkoxy, haloalkoxy, aryloxy, alkylthio and alkoxycarbonyl, and when R1 is alkyl or alkoxy, or, when W is nitrogen, R2 can also be unsubstituted phenyl, have pesticidal especially fungicidal activity.
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- Reaction of Aromatic Acyl Chlorides with Potassium or Sodium Cyanide Impregnated onto Amberlite XAD Resins. Efficient Synthesis of Aromatic Acyl Cyanides
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The effects of alkali metal cyanide impregnated on Amberlite XAD resins (KCN/XAD, NaCN/XAD) have been examined using the cyanation of benzoyl chloride.In benzene, benzoyl cyanide was obtained in a very high yield with high selectivity under mild conditions.It is proposed that the reaction occurs on the surface of the resin.On the basis of the result obtained in the absence of any solvent, the reactivity of KCN/XAD toward dimerization of benzoyl cyanide has been found to be much poorer than that of KCN in solution.Although the reaction of acyl chlorides with KCN/XADor NaCN/XAD in benzene gave various acyl cyanides in good to excellent yields, no aliphatic acyl cyanide could be obtained.
- Sukata, Kazuaki
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p. 1085 - 1090
(2007/10/02)
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- On the Preparation of Acyl Cyanides from Aldehydes
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The O-silylated cyanohydrins 3 prepared from the aldehydes 1 with trimethylsilyl cyanide are oxidized photochemically or thermally with N-bromosuccinimide to afford the acyl cyanides 4a-n.Scope and limitations of the procedure are discussed.
- Haerle, Helmut,Jochims, Johannes C.
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p. 1400 - 1412
(2007/10/02)
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- Process for the production of acyl cyanides (B)
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There are prepared acyl cyanides of the formula STR1 where R is a straight or branched chain alkyl group having 1 to 18 carbon atoms, preferably 1 to 10 carbon atoms, and which also can be substituted by one or more phenyl groups or halogen atoms, preferably chlorine, or R is preferably a cycloalkyl group having 3 to 8 carbon atoms, preferably cyclopropyl, which can have one or more 1 to 3 carbon atom alkyl or halogen, preferably chlorine, substituents wherein in all of the above set forth substitutions the halogen atoms and the phenyl groups are not on the carbon atom adjacent to the carbonyl group or R is a substituted phenyl group, a naphthyl group, a substituted naphthyl group or a five membered heterocyclic group, e.g., furyl, thienyl or alkyl substituted thienyl, wherein the substituents on the phenyl or naphthyl are halogen atoms, nitro groups or alkyl or alkoxy groups having 1 to 5 carbon atoms. The process comprises reacting an acyl halide of the formula in which R is as defined above and Hal is a chlorine or bromine atom, with a mixture consisting of about 0.1 to 5 equivalents of the alkali metal cyanide and about 0.05 to 2 equivalents of the copper (I) salt at a temperature of about 50° to 180° C in the presence of a carboxylic acid nitrile inert under the reaction conditions employed. Certain of the compounds are novel per se.
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