Month: June 2021

These common heterocyclic compound, 14227-17-9, name is 2,4,6-Trimethoxyaniline, 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. COA of Formula: C9H13NO3

Intermediate 4 (100 mg) was added to 3 MI of POCl3 at 0 C. 2,4, 6- TNMETHOXYBENZENAMINE (0.13 g) was added and the reaction mixture was stirred for 3 to 5 days. The ice bath was allowed to melt during the first couple of hours. After that, the POC13 suspension was dropped to 200 ml of vigorously stirred diisopropyl ether. The solid material was filtered off and washed with diisopropyl ether. The residue was immediately stirred in ETOAC/SATURATED aqueous NAHCO3 (1/1) (200 ML) for 1 hour. The EtOAc was dried using brine and NA2SO4 successively and evaporated. The residue was purified by preparative TLC using CH2CI2/MEOH (95/5) as the eluent or by precipitation in CH2CLZ/MEOH. Yield: 0.01 g of compound 36 (8%).

The synthetic route of 2,4,6-Trimethoxyaniline has been constantly updated, and we look forward to future research findings.

Reference:
Patent; JANSSEN PHARMACEUTICA N.V.; ARTS, Theodora, Joanna, Francisca; JANSSEN, Graziella, Maria, Constantina; JANSSEN, Herwig, Josephus, Margareta; JANSSEN, Jasmine, Josee, Werner; JANSSEN, Paul, Peter, Maria; JANSSEN, Maroussia, Godelieve, Frank; WO2004/74266; (2004); A1;,
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Synthetic Route of 22236-10-8, 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. 22236-10-8 name is 4-(Difluoromethoxy)aniline, 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.

Example 12; 2-ButyI-5-(4-chIorophenyl)-4-{[4-(difluoromethoxy)phenyl]amino}isothiazol-3(2H)-one 1,1-dioxide; 2-Butyl-4-chloro-5-(4-chlorophenyl)isothiazol-3(2H)-one 1,1-dioxide (0.2Og, 0.60mmol) and 4-(difiuoromethoxy)-aniline (0.19Og, 1.20mmol) were mixed in MeCN (2.5mL). The mixture was heated in a microwave reactor at 130 C for 15 mins, then additional 60 mins and then at 140 0C for 15 mins, then additional 30 mins. The mixture was evaporated and the residue was purified by column chromatography (ISOLUTE SI 20 g/70 mL), eluting with heptane, then DCM:heptane (25:75, then 50:50), to give the title compound (0.122g, 45%);

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

Reference:
Patent; ASTRAZENECA AB; WO2006/73363; (2006); A1;,
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Some common heterocyclic compound, 321-28-8, name is 1-Fluoro-2-methoxybenzene, molecular formula is C7H7FO, 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. Quality Control of 1-Fluoro-2-methoxybenzene

The crude product (1.0 g, 7.9 mmol) was dissolved in acetonitrile (15 mL) and N-bromosuccinimide (1.4 g, 8.7 mmol) was added and reacted at 70 C for 3 h. After the reaction was completed, most of the acetonitrile was distilled off, 30 mL of water was added, the mixture was stirred for 10 min and extracted with ethyl acetate (3 × 20 mL). The combined organic phases were dried over anhydrous magnesium sulfate and separated by column chromatography (pure petroleum ether as eluent) The brominated product (intermediate A_2c) was obtained as a light yellow oily liquid (1.4 g, yield 86%) oA-2c: SH (300 MHz; CDCl 3) 7.23-7.16 (2H, m), 6.82 (D, J = 8.7Hz), 3.86 (3H, s); delta (75MuEtazeta; CDC13) 152.3 (d, Jc, F = 249.0Hz), 147.1 (d, 119.6 (d, J = 21.1 Hz), 114.6 (d, J = 2.2 Hz), 111.9 (d, J = 8.2 Hz), 56.4

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 321-28-8, its application will become more common.

Reference:
Patent; Chinese Academy Of Sciences Chemical Institute; Yu Chuyi; Li Yixian; Jia Tengdun; Zhao Xuan; (27 pag.)CN104557654; (2017); B;,
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Related Products of 5467-58-3, A common heterocyclic compound, 5467-58-3, name is 1-Bromo-4-methoxynaphthalene, molecular formula is C11H9BrO, 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.

Under nitrogen conditions,To the magnetic stirrer,thermometer,6.6 g (27.9 mmol) was added to a 250 mL three-necked flask of a condenser.1-bromo-4-methoxynaphthalene,12.0 g (36.3 mmol) of 4-nitrophenyl-2-amino-9,9-dimethylhydrazine,10.6g (167.4mmol) of copper powder,23.1 g (167.4 mmol) of potassium carbonate,7.4 g (27.9 mmol) of 18-crown-6,Then add 57.2 ml of o-dichlorobenzene,Reacting at 170 C for 20 h;The mixture was filtered while hot, and o-dichlorobenzene was distilled off under reduced pressure. The crude product was recrystallized from ethanol and N,N-dimethylacetamide (V:V = 1:2.7) to give 4-nitrophenyl-4. ‘-Methoxynaphthyl-2-amino-9,9-dimethylhydrazine 10.2 g, yield 75%;

The synthetic route of 5467-58-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Jilin University; Chen Chunhai; Su Kaixin; Wang Daming; Sun Ningwei; Zhou Hongwei; Zhao Xiaogang; (24 pag.)CN108929297; (2018); A;,
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134364-69-5, name is 2,3-Difluoroanisole, belongs to ethers-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. category: ethers-buliding-blocks

The arylation coupling reaction: the reaction bottle nitrogen protection, the room temperature by the addition of 32.2 g 3 – chloro -2 – fluoro anisole, 31.2 g acetyl ethyl acetate and 160 ml DMF, added after stirring […] 4 g copper acetate, heating to 50 C reaction 8 h. After the reaction into the 300 ml saturated ammonium chloride aqueous solution quenching reaction, adding 200 ml ethyl acetate extraction three times, the combined organic layer, after drying with anhydrous sodium sulfate concentrated to dry, to obtain 25.8 g intermediate VII, purity 99.3%, the weight yield of 80.2%.

The synthetic route of 134364-69-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Aoruite Pharmaceutical Co., Ltd.; Che Fengfeng; Jiang Tao; Wang Aimin; Xu Chenke; (9 pag.)CN109956906; (2019); A;,
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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. 589-10-6, name is (2-Bromoethoxy)benzene, This compound has unique chemical properties. The synthetic route is as follows., COA of Formula: C8H9BrO

Same procedure as in lit.32 with modifications: a biphasic solution of 2-bromo-1-phenoxy ethane32b (20.0 g, 0.1 mol), NBu4HSO4 (33 g, 0.1 mol) in Et2O (400 mL) and 50% aqueous NaOH (100 mL) was vigorously stirred at rt for 4 h. The organic phase was washed with H2O (3 × 50 mL), the aqueous phases were extracted with Et2O (2 × 50 mL), the combined organic phases dried (MgSO4) and evaporated. 27b was purified by distillation (7.8 g, 65%) at 70 C, 28 Torr. The reaction in toluene as in lit.32b gave a weaker yield (40%).1H NMR (250 MHz, CDCl3): similar values as in lit.37 S.-R. Sheng, X.-L. Liu, X.-C. Wang, Q. Xin and C.-S. Song, Synthesis (2004), pp. 2833-2836. Full Text via CrossRef | View Record in Scopus | Cited By in Scopus (21)37

According to the analysis of related databases, 589-10-6, the application of this compound in the production field has become more and more popular.

Reference:
Article; Chevrier, Carine; Le Nouen, Didier; Defoin, Albert; Tarnus, Celine; Carbohydrate Research; vol. 346; 10; (2011); p. 1202 – 1211;,
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Related Products of 6851-80-5, 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. 6851-80-5, name is 1-(2-Methoxyphenyl)-N-methylmethanamine belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

General procedure: The mixture of secondary amine (1.01 mmol) and paraformaldehyde(1.01 mmol) in ethanol (3 mL) was refluxed for 1 h,until paraformaldehyde was dissolved. Then compound 5 or 6(100 mg, 0.34 mmol) was added in one portion. The reactionmixture was refluxed for 24e48 h. Ethanol was removed underreduced pressure. The residue was diluted with water and acidifiedwith an aqueous solution of hydrochloric acid (10%). The aqueousphase was washed with CH2Cl2, and then basified with saturatedNaHCO3 solution. The alkaline aqueous phase was again extractedwith CH2Cl2. The combined organic phase washed with brine, driedover Na2SO4, filtered and concentrated under reduced pressure toafford the corresponding crude aurone Mannich base derivatives.Additionally, compounds 8a-b and the corresponding 9a-b wereobtained in one pot.

The synthetic route of 1-(2-Methoxyphenyl)-N-methylmethanamine has been constantly updated, and we look forward to future research findings.

Reference:
Article; Li, Yan; Qiang, Xiaoming; Luo, Li; Yang, Xia; Xiao, Ganyuan; Liu, Qi; Ai, Jiachen; Tan, Zhenghuai; Deng, Yong; European Journal of Medicinal Chemistry; vol. 126; (2017); p. 762 – 775;,
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Application of 43229-65-8, 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. 43229-65-8, name is N-Benzyl-1-(4-methoxyphenyl)propan-2-amine belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

[0140] General procedure for Enantiomeric Separation of 2- benzylaminopropanes [(R)-10-14, (S)-10-14]. The appropriate racemic 2- benzylaminopropane (1 eq) was combined with the appropriate optically active mandelic acid (1 eq) in methanol (c= 0.5 M) and refluxed until the solution homogenized, then cooled to RT. The crystals were filtered, collected, and recrystallized twice from methanol (c = 0.3 M) to afford the optically active 2- benzylaminopropane ? mandelic acid salt. The salts were converted to the free amine for the purpose of collecting NMR and rotation data by partitioning the mandelic acid salt between 10% K2CO3 and CHCl3, drying organic extracts (Na2SO4) and evaporating; [0143] (R)-(-)-l-(4′-Methoxyphenyl)-2-benzylaminopropane [(R)-Il]. A sample of 3.02 g (11.8 mmol) of l-(4′-methoxyphenyl)-2-benzylaminopropane (42) was reacted with 1.8 g (11.8 mmol) f5rJ-(+)-mandelic acid to give 530 mg (35% based on enantiomeric abundance) of the free amine after workup. 1H NMR (CDCl3) delta 1.10 (d, 3H, J = 6.3 Hz), 2.57-2.76 (m, 2H), 2.88-2.94 (m, IH), 3.79 (s, 3H), 3.72-3.88 (m, 2H), 6.82 (d, 2H, J = 8.7 Hz), 7.07 (d, 2H, J= 8.4 Hz), 7.15-7.31 (m, 5H); MS (APCI+) m/z (rel): 256 (100); [alpha]D = -30.4 (c = 1.25 MeOH).

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, N-Benzyl-1-(4-methoxyphenyl)propan-2-amine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; THE GOVERNMENT OF THE UNITED STATES OF AMERICA AS REPRESENTED BY THE SECRETARY OF THE DEPARTMENT OF HEALTH AND HUMAN SERVICES; WO2008/22038; (2008); A1;,
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Adding a certain compound to certain chemical reactions, such as: 74137-36-3, name is 1,3-Dibromo-5-methoxybenzene, belongs to ethers-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 74137-36-3, Recommanded Product: 74137-36-3

To a solution of 1,3-dibromo-5-methoxybenzene (9.18 mmol, 1 eq) in 2 ml of xylene under a nitrogen atmosphere, acrylic acid (0.63 ml, 9.18 mmol, 1 eq), Pd(OAc)2 (1 mole percent, 20.66 mg), triphenylphosphine (4 mole percent, 69.2 mg) and triethylamine (19.278 ml, 2.7, 2.1 eq) are added. The reaction mixture is stirred at 100° C. for 11 h. Thereafter, 20 ml of water and 2 g of sodium carbonate were added, and the mixture was stirred at 100° C. for some minutes. The aqueous phase was subsequently separated and acidified. The precipitate that formed was dried and purified by means of column chromatography (eluent hexane/ethyl acetate 1/1) to obtain the desired product in a yield of 32percent (751 mg). C10H9Br3O; MW 256/258; 1H-NMR (CD3OD): delta 7.61 (d, J=16.1 Hz, 1H), 7.38-7.37 (m, 1H), 7.17-7.16 (m, 2H), 6.53 (d, J=16.1 Hz, 1H), 3.87 (s, 3H); 13C-NMR (CD3OD): delta 169.8, 162.3, 144.5, 138.9, 124.2, 121.4, 120.0, 113.4, 56.2

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, 1,3-Dibromo-5-methoxybenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Hartmann, Rolf; Frotscher, Martin; Oberwinkler, Sandrine; Ziegler, Erika; Messinger, Josef; Thole, Heinrich-Hubert; US2010/204234; (2010); A1;,
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Adding a certain compound to certain chemical reactions, such as: 22171-15-9, name is (4-(Benzyloxy)phenyl)methanamine, belongs to ethers-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 22171-15-9, SDS of cas: 22171-15-9

2,6-Diamino-nicotinic acid described in Preparation Example A-15 (0.6g, 3.92mmol), triethylamine (1.64mL, 11.8mmol) and benzotriazole-1-yloxy tris(dimethylamino)phosphonium hexafluorophosphate (2.6g, 5.9mmol) were dissolved in N,N-dimethylformamide (200mL), 4-benzyloxy-benzylamine described in Preparation Example 1 (1.25g, 5.9mmol) was added thereto, and the solution was stirred at room temperature for 16 hours. After the reaction was completed, the reaction solution was poured into brine, and the solution was extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, then concentrated, the obtained residue was purified by NH silica gel column chromatography (ethyl acetate : hexane = 2 : 1, then ethyl acetate), the resulting solid was washed with solvent (chloroform : ethyl acetate = 2 : 1), and the title compound (0.37g, 1.1 mmol, 27%) was obtained. 1H-NMR Spectrum (DMSO-d6) delta(ppm) : 4.29 (2H, d, J=6.0Hz), 5.07 (2H, s), 5.66 (1H, d, J=8.4Hz), 6.06 (2H, br s), 6.91-6.97 (4H, m), 7.19 (2H, d, J=8.8Hz), 7.29-7.45 (5H, m), 7.65 (1H, d, J=8.4Hz), 8.27 (1H, t, J=6.0Hz).

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, (4-(Benzyloxy)phenyl)methanamine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Eisai Co., Ltd.; EP1669348; (2006); A1;,
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