Tag: M.W=200-300

Electric Literature of 33529-02-1, These common heterocyclic compound, 33529-02-1, name is 1-Decyl-1H-imidazole, 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.

General procedure: In a 250 mL two-neck round bottom flask equipped with a condenser linked to the vacuum-argon line, N-butylimidazole (title 99% w/w, Alfa Aesar) (4.2 g, 33.4 mmol) was charged and after degassing with three vacuum/argon cycles, 1H,1H,2H,2H-perfluorooctyliodide 96% w/w, Aldrich) (23.8 g, 50.1 mmol) was added. After three more vacuum/argon cycles the temperature of the oil bath was increased from 25 C to 120 C in 10 min. After heating for 6 h, NMR analysis of the crude reaction mixture (Fig. 6S, ESI) showed that the reaction went to completion and the occurrence, together with the target molecule C4-I, of the by-products N-butyl-imidazolium iodide and 1H,1H,2H-perfluoro-1-octene ( Scheme 1 ) typical of a Hofmann elimination of the imidazolium salts [29-31]. By cooling the presence of two phases was observed: a viscous red liquid (containing C4-I, N-butyl-imidazolium iodide and C6F13CH = CH2) at the top and a pale yellow liquid (the unreacted 1H,1H,2H,2H-perfluorooctyl iodide with C6F13CH = CH2) at the bottom. The phases were separated by decantation and the viscous red liquid washed three times with petroleum ether (3 * 50 mL) and three times with diethyl ether (3 * 50 mL). The solvent and the volatile by-product C6F13CH = CH2 (bp = 102-104) were eliminated under vacuum (30 C/53 Pa). After the work-up 1H NMR of the red oil showed peaks of C4-I (75%) and of N-butyl-imidazolium iodide (25%). The raw product (20 g) was dissolved in 20 mL of dichloromethane and filtered under argon on anhydrous celite (40 g) previously wetted with 200 mL of dichloromethane. The filtration was repeated two times. Celite was then washed with 80 mL of dichloromethane. Evaporation of the solvent (30 C/53 Pa) gives a red sticky wax with a yield of 75.1% (15.0 g, 25 mmol).

Statistics shows that 1-Decyl-1H-imidazole is playing an increasingly important role. we look forward to future research findings about 33529-02-1.

Reference:
Article; Zama, Isabella; Gorni, Giacomo; Borzatta, Valerio; Cassani, Maria Cristina; Crupi, Cristina; Di Marco, Gaetano; Journal of Molecular Liquids; vol. 223; (2016); p. 749 – 753;,
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Related Products of 71759-87-0, 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. 71759-87-0, name is 4-Iodo-1-methyl-1H-imidazole belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

[0297] To a solution of 4-iodo-l -methyl- lH-imidazole (34.0 g, 163 mmol) in THF (300 mL) at -10 C was added isopropylmagnesium chloride (25.0 g, 244 mmol) dropwise under N2. The mixture was stirred for 1 h at this temperature, and then tributylchlorostannane (55.6 g, 171 mmol) was added drop-wise. The reaction was stirred at room temperature overnight under N2. The reaction mixture was diluted with saturated aqueous NH4Cl (400 mL) and extracted with EtOAc (200 mL x 3). The combined organic phases were washed with water (200 mL x 2) and brine (200 mL), dried over Na2S0, and concentrated to dryness, to afford the desired product (65.0 g, 100 %) as colourless oil, which was used in the next step directly. [0298] LC-MS (Agilent): Rt 2.84 min; m/z calculated for Ci6H32N2Sn [M+H] + 373.2, found 373.2

The synthetic route of 4-Iodo-1-methyl-1H-imidazole has been constantly updated, and we look forward to future research findings.

Reference:
Patent; EPIZYME, INC.; HARVEY, Darren Martin; CAMPBELL, John Emmerson; DUNCAN, Kenneth William; (246 pag.)WO2019/108824; (2019); A1;,
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These common heterocyclic compound, 37148-86-0, name is 4-(4-(Trifluoromethyl)phenyl)-1H-imidazole, 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. SDS of cas: 37148-86-0

Sodium hydride (60% in oil) (32 mg) was added at 0 C. to a DMF (6.7 mL) solution of Reference Example 2 (0.17 g), and the mixture was stirred at 0 C. for 30 minutes. 2-Fluoro-4- (trifluoromethyl) benzonitrile (0.13 g) was added to the reaction solution at 0 C., and the mixture was stirred at room temperature for 3 hours. Water was added to the reaction solution, and the mixture was extracted with ethyl acetate. The obtained organic layer was washed with a saturated saline solution and dried over sodium sulfate. After evaporation of the solvent of the organic layer after drying under reduced pressure, the obtained residue was purified by silica gel chromatography (elution solvent; hexane: ethyl acetate) to obtain Reference Example 5 (0.18 g).

The synthetic route of 4-(4-(Trifluoromethyl)phenyl)-1H-imidazole has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SUMITOMO DAINIPPON PHARMA COMPANY LIMITED; ISOBE, YOSHIAKI; BAN, HITOSHI; SAITO, YASUHIRO; WATANABE, HITOSHI; (44 pag.)JP2018/135270; (2018); 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. 641571-11-1, name is 3-(4-Methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)aniline, This compound has unique chemical properties. The synthetic route is as follows., name: 3-(4-Methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)aniline

Example 2[69] Synthesis of 4-methyl-N-[3-(4-methylimidazole-l-yl)-5-trifluoromethyl-phenyl] -3-(4-pyrazine-2-yl-pyrimidine-2-yl amino)benzamide[70][71] Method A[72] A pale yellow solid final compound (18.7g, yield 85%) was obtained by reacting3-(4-methyl-imidazole-l-yl)-5-trifluoromethyl-phenylamine (1Og, 41.46mmol) with 4-methyl -3-(4-pyrazine-2-yl-pyrimidine-2-yl amino)-benzoic acid ethyl ester in a similar manner as described in Method A of Example 1, except that 4-methyl-3-(4-pyrazine-2-yl-pyrimidine-2-yl amino) -benzoic acid ethyl ester (15.3g, 45.60mmol) was used, instead of 4-methyl-3-(4-thiazole-2-yl-pyrimidine-2-yl amino)benzoic acid ethyl ester.[73] 1H-NMR(DMSOd , delta= 2.21(s,3H), 2.38(s,3H), 7.35(s,lH), 7.39(s,lH), 7.54(s,lH),7.63(d,lH), 7.75(d,lH), 8.14(d,2H), 8.38(d,2H), 8.54(d,2H), 8.68(s,lH), 9.06(s,lH), 9.45(s, IH), 10.56(s,lH)

According to the analysis of related databases, 641571-11-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; IL-YANG PHARM. CO., LTD.; KIM, Dong Yeon; CHO, Dae Jin; LEE, Gong Yeal; KIM, Hong Youb; WOO, Seok Hun; WO2010/18895; (2010); A1;,
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Reference of 641571-11-1,Some common heterocyclic compound, 641571-11-1, name is 3-(4-Methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)aniline, molecular formula is C11H10F3N3, 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.

Example 1; [240] Preparation of N-r3-f4-methylimidazol- l-ylV5-trifluoromethyl-phenyll-4-(4-pyridin-3-yl-Pyrimidin-2-ylaminos)-benzamide; EPO [241] 4-(4-pyridin-3-yl-pyrimidin-2-ylamino)-benzoic acid prepared in Preparation 19(242mg, 0.83mmol) and 3-(4-methyl-imidazol- l-yl)-5-trifluoromethyl-phenylamine prepared in Preparation 30 (200mg, 0.83mmol), N,N-dimethyl formamide (10ml), and diethylcyano phosphate ( 0.245ml, 1.658mmol) were added to a reaction vessel, and cooled to 100C. Triethylamine (0.231ml, 1.658mmol) was added thereto. After 30 min, the mixture was mixed at 600C for 15 hr. The mixture was cooled to RT, and an organic layer was obtained with the solution of ethyl acetate and sodium bi carbonate, concentrated under vacuum, and subjected to column chromatography (5: 1/CHC1 :MeOH) to give the titled compound as pale yellow solid.[242] 1H-NMR (DMSO-d , delta)= 2.20 (s,3H), 7.39 (s,lH), 7.56 (d,2H), 8.03 (m,5H), 8.17(s,lH), 8.21 (d,lH), 8.32 (s,lH), 8.49 (d,2H), 8.63 (d,lH), 8.72 (d,lH), 9.36 (s,lH), 10.15 (s, IH); 10.48 (s,lH)

The synthetic route of 641571-11-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; IL-YANG PHARM. CO., LTD.; WO2007/18325; (2007); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 5395-50-6, 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. 5395-50-6, name is 1,3,4,6-Tetrakis(hydroxymethyl)tetrahydroimidazo[4,5-d]imidazole-2,5(1H,3H)-dione belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

1 ,3,4,6-tetrakis(hydroxymethyl)tetrahydroimidazo [4,5-d]imidazole-2,5(1H,3H)-dione (1.99 g, 7.6 mmol) in 1.5 ml of DM50 was dissolved. Then, 0.3 ml nitric acid (65%) and 4-ethylcyclohexanol (10.5 ml, 75.9 mmol) were added to the solution and the mixture was heated at 60 C. for 16 hours. After the reaction was over, the reaction liquid was cooled and iN NaOH was added around pH 7. Around 100 ml ethyl acetate was used to extract with mixture and the organic phase was washed by saturated NaC1(aq) solution for 2 times. Afier being dried by Na2SO4, the solvent was removed

The synthetic route of 1,3,4,6-Tetrakis(hydroxymethyl)tetrahydroimidazo[4,5-d]imidazole-2,5(1H,3H)-dione has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Rohm and Haas Electronic Materials LLC; Rohm and Haas Electronic Materials Korea Ltd.; Grandbois, Matthew; Kim, Myung Yeol; Ryu, Eui Hyun; Sim, Jae Hwan; Jang, Min Kyung; Lee, Jung-June; (17 pag.)US2017/59991; (2017); A1;,
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Imidazole | C3H4N2 – PubChem

Synthetic Route of 870837-18-6, 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. 870837-18-6, name is 3-Methoxy-4-(4-methyl-1H-imidazol-1-yl)benzaldehyde belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

t-BuLi (0.188 ml_, 0.32 mmol, 1.7 M) was added dropwise to a solution of compound D6 ((S), R6 = H, R7 = Ph; 46 mg, 0.21 mmol) in THF (1.5 ml_) at -78 0C. The mixture was stirred for 45 minutes before compound D7 (R10 = 3-MeO- Phenyl, R9 = 4-(4-methylimidazol-1-yl)) was added in THF (1.0 ml_) in fast drops. The resulting mixture was stirred for 2 hours before it was diluted with EtOAc (50 ml_) and NH4CI solution (10 mL). The organic layer was washed with brine, dried over MgSO4, and concentrated to give the crude product which was purified by column chromatography eluting with EtOAc/hexanes to yield compound D8 ((S), R6 = H, R7 = Ph; R10 = 3-MeO-Phenyl, R9 = 4-(4-methylimidazol-1 -yl)).

The synthetic route of 3-Methoxy-4-(4-methyl-1H-imidazol-1-yl)benzaldehyde has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SCHERING CORPORATION; WO2008/153793; (2008); A2;,
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Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 791595-74-9, name is 5-Bromo-1H-benzo[d]imidazol-2-amine, belongs to imidazoles-derivatives 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 791595-74-9, Recommanded Product: 791595-74-9

The corresponding HCl salt of 11 was prepared for biological testing by dissolving 5-bromo-2-aminobenzimidazole (11, 100 mg, 0.47 mmol, 1.0 eq.) in 1,4-dioxane (5 mL) and adding 4.0 M HCl in 1,4-dioxane (589 muL, 2.36 mmol, 5.0 eq.) The resulting precipitate was filtered and dried in vacuo at 50 C. to yield a red crystalline solid. [0219] 1H NMR (300 MHz, DMSO-d6) delta 7.32 (dd, 1H, J=8.4, 0.6 Hz), 7.36 (dd, 1H, J=8.4, 1.7 Hz), 7.55 (dd, 1H, J=1.7, 0.6 Hz), 8.72 (s, 2H), 12.77 (bs, 2H); 13C NMR (75 MHz, DMSO-d6) delta 113.1, 114.1, 114.5, 125.6, 129.1, 131.2, 150.9; ESI-MS: calculated m/z [M+H]+ 211.9818, observed m/z 211.9811.

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; BLACKWELL, Helen; Frei, Reto; Breitbach, Anthony; Lynn, David M.; Broderick, Adam H.; US2013/136782; (2013); A1;,
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Imidazole | C3H4N2 – PubChem

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. 2963-77-1, name is 4-(1H-Benzo[d]imidazol-2-yl)aniline, A new synthetic method of this compound is introduced below., Safety of 4-(1H-Benzo[d]imidazol-2-yl)aniline

General procedure: A suspension of amine A1-A3 (1 mmol) in water is takenin a round bottomed flask; to this sulphonyl chloride(1 mmol) was added. This was stirred at room temperature while monitoring the reaction. The product was filtered,recrystallised using methanol-water and column purified.The structures were confirmed by 1H NMR, 13C NMR, IRand mass spectral analysis.

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:
Article; Vangala, Radhika; Sivan, Sree Kanth; Peddi, Saikiran Reddy; Manga, Vijjulatha; Journal of Computer-Aided Molecular Design; vol. 34; 1; (2020); p. 39 – 54;,
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Related Products of 870837-18-6, 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. 870837-18-6, name is 3-Methoxy-4-(4-methyl-1H-imidazol-1-yl)benzaldehyde belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

Under ice-cooling, L-selectride (1.3 mL, 1.02 M tetrahydrofuran solution) was added dropwise into a tetrahydrofuran (13 mL) solution containing (6S,8aR)-1,1-cyclopropyl-6-(3,4,5-trifluorophenyl)tetrahydropyrrolo[2,1-c][1,4]oxazine-3,4-dione (377 mg). Stirring was continued for 40 minutes at the same temperature. A 5 N sodium hydroxide solution (251 muL) was added to the reaction solution, and stirring was continued for 10 minutes at 0 C., and next hydrogen peroxide solution (245 muL, 35% solution) was added, and stirring was continued for 10 minutes at 0 C. Sodium bisulfite (260 mg) was added, and after stirring for 20 minutes at room temperature, ethyl acetate and brine were added, and the organic layer was partitioned. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was removed under a vacuum. Acetonitrile (13 mL) and triphenyl phosphonium bromide (439 mg) were added to the residue, and the resultant was heated under reflux for 1 hour. The resultant was returned to room temperature, and 3-methoxy-4-(4-methyl-1H-imidazol-1-yl)benzaldehyde (299 mg) and triethylamine (348 {L) were added, and stirring was continued for 12 hours at room temperature. Ethyl acetate and brine were added to the reaction solution, and the organic layer was partitioned. The resultant was dried over anhydrous magnesium sulfate, and the solvent was removed under a vacuum. The residue was crudely purified by silica gel column chromatography (carrier: Chromatrex NH, eluting solvent: hexane/ethyl acetate?ethyl acetate). A crude material (100 mg) containing the title compound was obtained. The resulting crude material (20 mg) was purified by Daicel CHIRALPAK IA (2cm¡Á25 cm: transition phase; hexane/ethanol 1/1), and the title compound (3.8 mg) was obtained. The physical property values are as follows.ESI-MS; m/z 496 [M++H]. 1H-NMR (CDCl3) delta (ppm): 0.91-0.96 (m, 1H), 1.01-1.13 (m, 2H), 1.32-1.41 (m, 2H), 1.82-1.94 (m, 2H), 2.29 (s, 3H) 2.37-2.46 (m, 1H), 3.83 (s, 3H), 4.61 (dd, J=11.6, 4.8 Hz, 1H), 5.18 (d, J=8.8 Hz, 1H), 6.80 (s, 1H), 6.86 (dd, J=8.0, 6.0 Hz, 2H), 6.91 (dd, J=1.2, 1.2 Hz, 1H), 7.18 (d, J=8.0 Hz, 1H), 7.26 (dd, J=8.4, 1.6 Hz, 1H), 7.36 (d, J=1.2 Hz, 1H), 7.70 (d, J=1.6 Hz, 1H).

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, 3-Methoxy-4-(4-methyl-1H-imidazol-1-yl)benzaldehyde, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; KIMURA, Teiji; Kawano, Koki; Doi, Eriko; Kitazawa, Noritaka; Takaishi, Mamoru; Ito, Koichi; Kaneko, Toshihiko; Sasaki, Takeo; Sato, Nobuaki; Miyagawa, Takehiko; Hagiwara, Hiroaki; US2008/207900; (2008); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem