Tag: M.W=100-200

33543-78-1, 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. 33543-78-1, name is Ethyl 1H-imidazole-2-carboxylate, This compound has unique chemical properties. The synthetic route is as follows.

Example 92 A mixture of 4-[4-(4-chlorophenyl)-2-(2-methyl-1-imidazolyl)-5-oxazolyl]butyl methanesulfonate(600 mg), ethyl 2-imidazolecarboxylate(410 mg), potassium carbonate(405 mg) and N,N-dimethylformamide (30 ml) was stirred for 2 hours at 80-90¡ã C. Water was added to the reaction mixture. This was extracted with ethyl acetate. The ethyl acetate layer was washed with water and dried (Mg SO4). The residue obtained by evaporating the solvent was subjected to silica gel column chromatography. From the fraction eluted with acetone-hexane (1:1, v/v), obtained was ethyl 1-[4-[4-(4-chlorophenyl)-2-(2-methyl-1-imidazolyl)-5-oxazolyl]butyl)-2-imidazolecarboxylate as crystals (460 mg, 69percent). This was recrystallized from acetone-isopropyl ether to give colorless prisms. mp 134-135¡ã C.

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Reference:
Patent; Takeda Chemical Industries, Ltd.; US6177452; (2001); B1;,
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104-98-3, A common heterocyclic compound, 104-98-3, name is 3-(1H-Imidazol-4-yl)acrylic acid, molecular formula is C6H6N2O2, 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.

Urocanic acid (32) (4.74 g, 34.33 mmol), amine 33 (5.5 g, 34.33 mmol) and HOBt (5.26 g, 34.33 mmol) were suspended/dissolved in DMF (50 mL) and the mixture was cooled to 0 C. N-(3-Dimethylaminopropyl)-N’-ethylcarbodiimide hydrochloride (6.91 g, 36.05 mmol) was added and the mixture was slowly warmed to rt and stirred overnight (The suspension turned to a clear orange solution after 2 h). The mixture was diluted with 2.5% aq NaOH (500 mL) and brine (100 mL). Repeated treatment with EtOAc (12 * 200 mL) afforded an extraction of product 34 only in low amounts and extraction with CHCl3 (2 * 150 mL) failed as well. Therefore, the aqueous phase was concentrated under reduced pressure at 40 C to a volume of 300 mL and then treated twice with CHCl3/MeOH 5:1 (500 and 400 mL). The organic phases were combined with the earlier EtOAc and CHCl3 extracts and removal of the volatiles under reduced pressure yielded a yellow liquid (ca 50 mL). DMF was removed under reduced pressure (50 C, 10 mbar) and the residue was subjected to column chromatography (eluent: CH2Cl2/MeOH 50:1 to 10:1). Removal of the solvent from the eluate under reduced pressure, uptake in CH2Cl2 (80 mL), evaporation, uptake in CH2Cl2 (50 mL) followed by removal of the solvent in vacuo afforded 34 as a white powder (8.27 g, 86%), mp 159-161 C. A minor fraction was recrystallized from acetone/EtOAc to yield colorless needles, mp 165-167 C. Rf = 0.6 (CH2Cl2/MeOH 5:1). Anal. calcd for C13H20N4O3: C, 55.70; H, 7.19; N, 19.99; found: C, 55.65; H, 7.29; N, 19.86. IR (Nujol) 3355, 3300, 1685, 1665, 1630, 1530 cm-1. 1H NMR (400 MHz, CD3OD) delta (ppm) 1.46 (s, 9H), 3.23 (t, 2H, J 6.2 Hz), 3.39 (t, 2H, J 6.2 Hz), 6.52 (d, 1H, J 15.6 Hz), 7.36 (s, 1H), 7.46 (d, 1H, J 15.6 Hz), 7.77 (s, 1H). 13C NMR (100 MHz, CD3OD) delta (ppm) 29.6, 41.5, 42.0, 81.0, 120.1, 123.2 (br), 133.1, 137.5 (br), 139.2, 159.4, 170.2. MS (ESI, MeOH) m/z (%) 583 (76) [2M+Na]+, 319 (38) [M+K]+, 303 (100) [M+Na]+, 281 (17) [M+H]+, 203 (26) [M-C4H8-CO2+Na]+, 181 (22) [M-C4H8-CO2+H]+, C13H20N4O3 (280.32).

The synthetic route of 104-98-3 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Keller, Max; Traenkle, Christian; She, Xueke; Pegoli, Andrea; Bernhardt, Guenther; Buschauer, Armin; Read, Roger W.; Bioorganic and Medicinal Chemistry; vol. 23; 14; (2015); p. 3970 – 3990;,
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The chemical industry reduces the impact on the environment during synthesis 705-09-9, name is 2-(Difluoromethyl)-1H-benzo[d]imidazole, I believe this compound will play a more active role in future production and life. 705-09-9

A mixture of 2-difluoromethyl-lH-benzimidazole (2.22 g), 2,4-dichloro- 6-morpholinopyrimidine (2.81 g), potassium carbonate (6.63 g) and DMF (50 ml) was stirred under nitrogen and heated to 900C for 16 hours. The resultant mixture was cooled, filtered and the filtrate was evaporated. The resultant product was purified by column chromatography on silica using increasingly polar mixtures of ethyl acetate in methylene chloride as eluent. The solid so obtained was washed with a 1 :1 mixture of isohexane and diethyl ether. There was thus obtained 4-chloro-2-(2-difluoromethylbenzimidazol- 1 -yl)-6-morpholinopyrirnidine (3.17 g); NMR Spectrum: (DMSOd6) 3.75 (s, 8H), 7.09 (s, IH), 7.45-7.47 (m, IH), 7.50-7.54 (m, IH), 7.57-7.83 (t, IH), 7.87 (d, IH), 8.31 (d, IH); Mass Spectrum: M+H1″ 366.

The chemical industry reduces the impact on the environment during synthesis 705-09-9. I believe this compound will play a more active role in future production and life.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; BUTTERWORTH, Sam; GRIFFEN, Edward, Jolyon; PASS, Martin; WO2008/32086; (2008); A1;,
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1003-21-0, Adding a certain compound to certain chemical reactions, such as: 1003-21-0, name is 5-Bromo-1-methyl-1H-imidazole, 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 1003-21-0.

Example 5; N1-(3-Fluoro-4-(2-(1-methyl-1H-imidazol-5-yl)thieno[3,2-b]pyridin-7-yloxy)phenyl)-N3-phenylmalonamide (5e) Step 1: 7-Chloro-2-(1-methyl-1H-imidazol-5-yl)thieno[3,2-b]pyridine (16); Nitrogen was bubbled through a mixture of the tin derivative 6 (7.19 g, 15.7 mmol) and 5-bromo-1-methyl-1H-imidazole (2.02 g, 12.5 mmol) [a) Begtrup, M.; Larsen, P.; Acta Chem. Scand. 44, 10; 1990; 1050-1057. b) Begtrup, M.; Bull. Soc. Chim. Belz.; 97; 8-9; 1988; 573-598. c) Begtrup, M.; Larsen, P.: Chem. Pharm. Bull. 42, 9; 1994; 1784-1790.] in toluene (20 mL) for 5 minutes. Pd(PPh3)4 (1.50 g, 1.30 mmol) was added and nitrogen was bubbled for additional 5 minutes. Finally, the mixture was refluxed under nitrogen overnight, the resultant yellow suspension was concentrated under reduced pressure and then purified with flash chromatography (eluent EtOAc/MeOH 90:10), to afford title compound 16 as a yellow solid (2.48 g, 79% yield). MS (m/z): 250.0(M+H).

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, 5-Bromo-1-methyl-1H-imidazole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Methylgene, Inc.; US2007/4675; (2007); A1;,
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In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 41716-18-1 as follows. 41716-18-1

A mixture of (+/-)-ferf-butyl ((c/s)-3-aminocyclohexyl)carbamate (5 g, 23.3 mmol) and DMAP (7.1 g, 58.3 mmol) in CH2CI2 (100 mL) was stirred at ambient temperature, then 1 -methyl-1 h-imidazole-4-carboxylic acid (2.9 g, 23.3 mmol) was added. After stirring for 10 minutes at room temperature, EDC (6.7 g, 35 mmol) was added. The mixture stirred for 18h at room temperature. The reaction mixture was washed with citric acid (5percent aq.), the organic layer was removed, dried (MgS04), the solids removed by filtration, and the solvent of the filtrate removed under reduced pressure to give (+/-)-f-butyl ((c/’s)-3-(1 -methyl-1 – -imidazole-4- carboxamido)cyclohexyl)carbamate. LC-MS ES+ m/z = 323.5; Rt: 0.75 min, method A.

According to the analysis of related databases, 41716-18-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; JANSSEN SCIENCES IRELAND UC; JONCKERS, Tim, Hugo, Maria; RABOISSON, Pierre, Jean-Marie, Bernard; GUILLEMONT, Jerome, Emile, Georges; MC GOWAN, David, Craig; EMBRECHTS, Werner, Constant, Johan; COOYMANS, Ludwig, Paul; MICHAUT, Antoine, Benjamin; (162 pag.)WO2016/20526; (2016); A1;,
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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. 22884-10-2, name is 2-(1H-Imidazol-1-yl)acetic acid, This compound has unique chemical properties. The synthetic route is as follows., 22884-10-2

48.87 g (0.4 mol) of 3,4-diaminotoluene and 63.05 g (0.5 mol) of 1-imidazole-1-acetic acid were weighed into a 1000 mL three-necked flask and 375 mL of 4 mol / L hydrochloric acid was added The mixture was stirred for 20 h at room temperature. The solution was reddish-brown and then refluxed at 100 C for 15 h. The solution gradually deepened and finally dark brown. After cooling, the reaction solution was poured into 1000 mL of distilled water and adjusted to pH 7-8 with ammonia. A large amount of precipitate was collected, suction filtered and then recrystallized from hot water to obtain 33.02 g of yellow crystals (yield: 38.89%).

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; Henan Polytechnic Institute; Huang, Qiuying; Lin, Xichang; Yang, Yi; Liu, Wei; Liu, Chunli; Su, Mingyang; Chen, Xiaodong; Du, Xikun; Shen, Gang; Fang, Lei; Meng, Xiangru; (8 pag.)CN104610310; (2016); B;,
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496-46-8, Name is Tetrahydroimidazo[4,5-d]imidazole-2,5(1H,3H)-dione, 496-46-8, belongs to imidazoles-derivatives compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows.

Synthesis of cucurbit[n]urils in methanesulphonic acid usingDipropoxymethane (Propylal)Unsubstituted glycoluril (19.94 g) and methane sulphonic acid (neat, 82 mL) were placed in a reaction flask and heated to 80 C. Propylal (45 mL) was added in drop-wise and the reaction mixture was then heated to 100 C (internal temp) for 18 hours. The reaction mixture was cooled and added to acetone (410 ml) to produce a beige powder which was analysed by1H NMR. Approximate Yields by1H NMR (% of recovered product) cucurbit[5]urii 0%, cucurbit[8]uril 58%, cucurbit[7]uril 42%, cucurbit[8]uril 0%, cucurbit[9]uril 0%, cucurbit[10]uril 0%, cucurbit[11]urii 0%. Residual formaldehyde by HPLC method was 5 ppm.

Statistics shows that Tetrahydroimidazo[4,5-d]imidazole-2,5(1H,3H)-dione is playing an increasingly important role. we look forward to future research findings about 496-46-8.

Reference:
Patent; AQDOT LIMITED; COULSTON, Roger; DIEC, David; NOGUEIRA, Guilherme; GERARDUS DE ROOIJ, Johannes; (23 pag.)WO2018/115822; (2018); A1;,
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583-39-1, 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. 583-39-1, name is 2-Mercaptobenzimidazole belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

To the solution of PdCl2(PPh3)2 (0.050 g, 0.07 mmol) dissolvedin 10 mL of CH3CN, bzimSH (0.021 g, 0.14 mmol) was added followedby Et3N base (0.5 mL). The solution became turbid and yellowishorange in color. Then the refluxing was done for 6 h. Thecolor of the reaction mixture became orange and was filtered.The filtrate was evaporated using rotary evaporator until a solidwas obtained. It was treated with acetone which dissolved thecomplex leaving behind Et3NH+Cl, white solid. The acetone solutionwas filtered to remove Et3NH+Cl. To it was added 4 mLdichloromethane-methanol (1:1, v/v) mixture and left to evaporateat room temperature. The orange colored crystals of compound2 were formed in a period of 10-15 days (67%, m.p 218-220 C). Anal. Calc. for C75H61ClN6P3Pd2S32H2O (1519.67): C,59.22; H, 4.01; N, 5.53. Found: C, 59.80; H, 4.36; N, 5.52%. IRbands(KBr, cm1): nu(O-H), 3393m (b); m(C-H), 3051m, 2963w; nu(C-C) + nu(C-N) + delta(C-H), 1618s, 1479m, 1433s, 1391s, 1263m,1226w;, 1182 w; nu(P-CPh), 1096s; nu(C-S) 1022s; 802m, 741s,691s, nu(Pd-N), 523s; 422w. ESI Mass could not be recorded dueto poor solubility.

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

Reference:
Article; Lobana, Tarlok S.; Sandhu, Amanpreet K.; Mahajan, Rakesh K.; Hundal, Geeta; Gupta, Sushil K.; Butcher, Ray J.; Castineiras, Alfonso; Polyhedron; vol. 127; (2017); p. 25 – 35;,
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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. 2034-23-3, name is 5-Chloro-1H-benzo[d]imidazol-2(3H)-one, A new synthetic method of this compound is introduced below., 2034-23-3

Preparation of 6-chloro-l -( 3-chloropropyl)-lH-benzo[Patent; ALTOS THERAPEUTICS, LLC; LUEHR, Gary, W.; SUNDARAM, Arathi; JAISHANKAR, Priyadarshini; PAYNE, Philip, W.; DRUZGALA, Pascal; WO2011/160084; (2011); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding some certain compound to certain chemical reactions, such as: 41716-18-1, name is 1-Methyl-1H-imidazole-4-carboxylic acid, 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 41716-18-1. 41716-18-1

1-methyl -1H- imidazole-4-carboxylic Acid (1eq) was dissolved in dimethylformamide (DMF) and, morpholine (1.01 eq) and 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide imide was added dropwise (EDC, 1.1 eq), 1- hydroxybenzotriazole (HOBT, 1.1 eq) and triethylamine (TEA, 3 eq) in sequence. After stirring overnight at room temperature, then terminate the reaction with a small amount of water, extracted with EtOAc and water and a small amount of water in the organic layer was removed by using anhydrous MgSO4, and evaporated under reduced pressure to remove the solvent and dried in vacuo. Then, separated by column to give the title compound in 45percent yield.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 1-Methyl-1H-imidazole-4-carboxylic acid.

Reference:
Patent; THE INDUSTRY & ACADEMIC COOPERATION IN CHUNGNAM NATIONAL UNIVERSITY (IAC); KIM, EUN HEE; YOO, SUNG EUN; KANG, NAM SOOK; KOO, TAE SUNG; PARK, MIN YOUNG; KIM, YOUNG HOON; BAE, HYUN JU; KIM, JIN WOO; IN, TAE KYU; JOO, CHOUN KI; (25 pag.)KR101555033; (2015); B1;,
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