Tag: M.W=100-200

Application of 1527-89-5, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 1527-89-5 name is 3-Methoxybenzonitrile, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

General procedure: To an oven-dried 15 mL sealed tube were added 2-aminophenylmethanol 1 (0.425 mmol), benzonitrile 2(0.25 mmol), Ru cat. b (1.94 mg, 1 mol%), and KOtBu (14.02 mg, 0.5equiv) intamyl alcohol (1 mL) under an air atmosphere. The sealedtube was capped and heated at 130C for 2 h. The reaction mixturewas cooled down to room temperature and directly concentratedunder vacuum. The crude mixture was puried by preparative thin-layer-chromatography (petroleum ether/ethyl acetate 20/1) togive the desired product 3 or 4.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3-Methoxybenzonitrile, and friends who are interested can also refer to it.

Reference:
Article; Wan, Xiao-Min; Liu, Zi-Lin; Liu, Wan-Qing; Cao, Xiao-Niu; Zhu, Xinju; Zhao, Xue-Mei; Song, Bing; Hao, Xin-Qi; Liu, Guoji; Tetrahedron; vol. 75; 18; (2019); p. 2697 – 2705;,
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Related Products of 628-20-6, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 628-20-6, name is 4-Chlorobutyronitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Under nitrogen protection, 0.5 L of tetrahydrofuran, 103.5 g (1 mol) of 4-chlorobutyronitrile, 2.52 g (0.02 mol) of anhydrous manganese chloride, 387 g (3 mol) of dimethyldichlorosilane,0.31 g of dibromoethane was added to the reactor, stirred and heated to 65 C.0.514g of magnesium turnings were added for the first time. After the reaction was initiated, 25.17g of magnesium turnings were added again for 2 hours. After the reaction was completed, the reaction product was subjected to solid-liquid separation, and the liquid phase was subjected to rectification, and the fraction was collected at a suitable temperature to obtain a cyano group. Organosilicon compound monomer (ie 3-cyanopropyldimethylchlorosilane). The yield of the obtained cyano group-containing organosilicon compound monomer was 96.1%, and the purity was 99.6%.

The synthetic route of 4-Chlorobutyronitrile has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Shandong Dongyue Silicone Materials Co., Ltd.; Yi Gang; Hu Qingchao; Wang Chunxiao; Liu Hailong; Guo Jianqiang; Li Yunjie; Sun Jiang; Xiao Yueling; (6 pag.)CN109879902; (2019); A;,
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Electric Literature of 214623-57-1,Some common heterocyclic compound, 214623-57-1, name is 5-Amino-2-methoxybenzonitrile, molecular formula is C8H8N2O, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

a 2-Methoxyl-5-N-[[4-morpholino]carbonyl]amino benzonitrile To a stirred mixture of 2-methoxyl-5-aminobenzonitrile (2 g, 12.34 mmol), and pyridine (1.28 g, 16.2 mmol) in dried CH2Cl2 (20 mL) was added 4-morpholinecarbonyl chloride (2.42 g, 16.2 mmol). After stirring at RT for 24 h, the mixture was diluted with CH2Cl2 and washed with H2O, brine, dried over MgSO4, concentrated to give an orange solid (3.04 g, 86%) 1H NMR: (400MHz, DMSO-d6): d 3.23 (t, J=4.9 Hz, 4H), 3.47 (t, J=4.9 Hz, 4H), 3.9 (s, 3H), 6.89 (d, J=9 Hz, 1H), 7.3 (d, J=9 Hz, 1H), 8.01 (s, 1H).

The synthetic route of 214623-57-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SmithKline Beecham Corporation; US6294531; (2001); B1;,
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Electric Literature of 123-06-8, These common heterocyclic compound, 123-06-8, name is Ethoxymethylenemalononitrile, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

To a mixture of Et3N (1.39 mL, 10 mmol) and cyclohexylhydrazine hydrochloride (1.51 g, 10 mmol) in EtOH (35 mL) was added ethoxymethylenemalononitrile (1.22 g, 10 mmol) portion wise. The reaction mixture was heated at reflux for 5 h, then cooled to room temperature and concentrated in vacuo. The residue was taken up in EtOAc (50 mL) and washed with water (2 x 25 mL). The organic phase was dried over Mg504, filtered and concentrated in vacuo to return 5-amino-1-cyclohexyl-pyrazole-4-carbonitrile (1.95 g, 103%) as an orange solid which was used without further purification. 1H NMR (300 MHz, CDCI3) O 7.49 (5, 1H), 4.45 (5, 2H), 3.77 (tt, =J= 11.2, 4.2 Hz, 1H), 1.88 (ddt, =J= 17.4, 11.4, 5.4 Hz, 6H), 1.83-1.65 (m, 1H), 1.49-1.32 (m, 1H), 1.38-1.15 (m, 2H).

The synthetic route of 123-06-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CANCER RESEARCH TECHNOLOGY LIMITED; JORDAN, Allan; NEWTON, Rebecca; (145 pag.)WO2017/178845; (2017); A1;,
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Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 53312-79-1, name is 3-Amino-4-chlorobenzonitrile, A new synthetic method of this compound is introduced below., name: 3-Amino-4-chlorobenzonitrile

Step A:2-Th ioxo-2 , 3-d ihyd robenzoth iazole-5-carbon itrile; A mixture of 3-amino-4-chlorobenzonitrile (200 mg, 1.32 mmol) and potassium o-ethyl- xanthate (422 mg, 2.64 mmol) in lambda/-methyl-2-pyrrolidone (1.5 ml.) was heated at 140 0C for 2 h. After cooling, the mixture was poured into ice-water. Then concentrated hydrochloric acid(0.2 ml.) was added. The solid was collected, washed with water and dried to give 2-thioxo-2,3-dihydrobenzothiazole-5-carbonitrile 250 mg (99 %).1H NMR (400 MHz, CDCI3): delta 7.53-7.50 (m, 2 H); 7.49 (s, 1 H).

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; NOVO NORDISK A/S; WO2007/110364; (2007); A1;,
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Adding a certain compound to certain chemical reactions, such as: 1009-35-4, name is 4-Fluoro-3-nitrobenzonitrile, belongs to nitriles-buliding-blocks compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 1009-35-4, COA of Formula: C7H3FN2O2

N-(4-Cvano-2-nitrophenyl)-N-methylglycineA mixture of 4-fluoro-3-nitrobenzonitrile (3.0 g) and sarcosine (2.53 g) with sodium hydrogen carbonate (2.39 g) in water (15 mL) and ethanol (15 mL) was heated at 8O0C. After 2 hours, the reaction was concentrated to half its volume and poured into IM HCl (50 mL). The aqueous solution was extracted with ethyl acetate and then with chloroform. The combined organic phases were dried over sodium sulfate and concentrated under reduced pressure. The residue was suspended in a minimum of dichloromethane and filtered yielding 3.74 g of product.MS TES): 236 (MH+) for Ci0H9N3O41H NMR (DMSO-D^ delta: 2.87 (s, 3H); 4.19 (s, 2H); 7.13 (d, IH); 7.82 (dd, IH); 8.29 (d,IH); 13.03 (s,lH).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4-Fluoro-3-nitrobenzonitrile, and friends who are interested can also refer to it.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2008/71981; (2008); A1;,
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Related Products of 7357-70-2, Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 7357-70-2, name is 2-Cyanothioacetamide, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: A mixture of the required acetophenones (0.001 mol),the appropriate aromatic aldehydes (0.001 mol), cyanothioacetamide(0.1 g, 0.001 mol) and ammonium acetate (0.62 g,0.008 mol) in n-butanol (10 mL) is irradiated at 150C for20 min in the microwave oven. After the reaction mixture iscooled to room temperature, the reaction mixture is dilutedwith 10 mL diethyl ether and the separated solid is filtered,dried and crystallized from ethanol to afford compounds 4-10.1,2-Dihydro-6-(3,4,5-trimethoxyphenyl)-4-(4-methoxyphenyl)-2-thioxopyridine-3-carbonitrile (4)Yellow powder, yield: 0.35g (87%), mp: 294-296C. IR(KBr, cm-1): 3421 (NH), 3066 (CH-aromatic), 2843 (CHaliphatic),2222 (CN), 1136 (C=S). 1H-NMR (400 MHz, dimethylsulfoxide (DMSO)-d6), delta ppm: 3.73 (s, 3H, OCH3),3.85 (s, 3H, OCH3), 3.88 (s, 6H, 2OCH3), 6.88 (s, 1H, Ar-H),7.13 (d, 2H, J=7.5 Hz, Ar-H), 7.20 (s, 2H, Ar-H), 7.72 (d, 2H,J=7.7 Hz, Ar-H), 12.53 (s, 1H, NH, D2O exchangeable).13CNMR(100 MHz, DMSO-d6), delta ppm: 55.9, 56.2 (2C), 56.7,97.7, 102.3, 105.8 (2C), 114.6 (2C), 117.4, 128.6, 129.5, 130.5(2C), 140.4, 153.5 (2C), 155.9, 161.5, 167, 169. Anal. Calcd for:C22H20N2O4S (408.47): C, 64.69; H, 4.94; N, 6.86. Found: C,64.93; H, 5.07; N, 7.04.

The chemical industry reduces the impact on the environment during synthesis 2-Cyanothioacetamide. I believe this compound will play a more active role in future production and life.

Reference:
Article; Elhameid, Mohammed K. Abd; Ryad, Noha; My, Al-Shorbagy; Mohammed, Manal R.; Ismail, Mohammed M.; El Meligie, Salwa; Chemical and Pharmaceutical Bulletin; vol. 66; 10; (2018); p. 939 – 952;,
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In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 148932-68-7, name is 2-Amino-3-methoxybenzonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Safety of 2-Amino-3-methoxybenzonitrile

To a solution of sodium thiocyanate (4.06 g) in methanol(70 mL) was added bromine (1.35 mL) at -700C. The reaction mixture was stirred for 10 min, and 2-amino-3- methoxybenzonitrile (3.71 g) was added. The temperature was risen to room temperature, and the mixture was stirred for 2 hr. The reaction mixture was poured into ice water, and the precipitated crystals were collected by filtration, washed with water and dried to give the title compound (4.28 g, yield 84%) as colorless crystals. Melting point 121-122C.

The synthetic route of 148932-68-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; TAKEDA SAN DIEGO, INC.; WO2008/156757; (2008); A1;,
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Synthetic Route of 6575-00-4, These common heterocyclic compound, 6575-00-4, name is 3,5-Dichlorobenzonitrile, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

step 1-A 100 ml round bottom flask was charged under a stream of nitrogen with 3,5-dichlorobenzonitrile (R-3a, 7.0 g, 40.69 mmol) and anhydrous DMF (75 mL). To the solution was added sodium methoxide (2.26 g, 44.76 mmol) and resulting solution was stirred further at RT for 24 h. When the reaction was complete, aqueous 10% HCl added dropwise to the reaction vessel. The crude mixture was extracted with EtOAc and sequentially washed with aqueous acid, water and brine. The EtOAc extracts were dried (Na2SO4), filtered and the solvent was removed in vacuo to afford a crude solid which was recrystallized from hexane/acetone to afford 5.9 g (86%) of R-3b.

The synthetic route of 6575-00-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Billedeau, Roland Joseph; Sweeney, Zachary Kevin; US2009/170856; (2009); A1;,
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Electric Literature of 1187-42-4,Some common heterocyclic compound, 1187-42-4, name is Diaminomaleonitrile, molecular formula is C4H4N4, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

General procedure: AlCl3 (15 molpercent) was added to a solution of DAMN (1 mmol), ketone (1 mmol) and isocyanide (1 mmol), in 5 ml of CH3CN. The resulting mixture was stirred for an appropriate time at room temperature. After completion of the reaction, as indicated by thin-layer chromatography (TLC; ethyl acetate=n-hexane 3=1), the product was precipitated by addition of 10 ml of water. The precipitate was filtered off, washed with water, and then recrystallized from acetone. In the case of aromatic aldehyde, precipitate after filtration was loaded on column chromatography with 20percent ethyl acetate?hexane as an eluent system to furnish the product.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Diaminomaleonitrile, its application will become more common.

Reference:
Article; Bhosale, Shrikar M.; Naik, Nilesh H.; Kusurkar, Radhika S.; Synthetic Communications; vol. 43; 23; (2013); p. 3163 – 3169;,
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