Tag: M.W=100-200

Application of 89830-98-8, The chemical industry reduces the impact on the environment during synthesis 89830-98-8, name is 5-Cyclopropyl-1H-imidazole, I believe this compound will play a more active role in future production and life.

[0357] To a solution of Example 18a (1.00 g, 3.67 mmol) in DMF (10 mL) were added Cul (351 mg, 1.83 mmol), Cs2C03 (2.38 g, 7.30mmol), Example 18b(476 mg, 4.41 mmol), andN1,N2-dimethyl- cyclohexane-l,2-diamine (105 mg, 0.74 mmol). The resulting mixture was degassed with N2 and stirred at 130°C under microwave for 2 h. The mixture was diluted with MeOH and filtered. The filtrate was concentrated under vacuum and the residue was purified byPrep-HPLC (by Ultimate XB-C18, 50 x 250 mm, 10 mum, speed: 80 mL/min, eluent: H20/CH3CN = from 80/20 to 20/80 over 50 min)to give the desired product Example 18c (110 mg, yield 12percent) as a yellow solid. LC-MS: [M+H]+ = 253.0

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-Cyclopropyl-1H-imidazole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; FRONTHERA U.S. PHARMACEUTICALS LLC; JIN, Bohan; DONG, Qing; HUNG, Gene; (227 pag.)WO2018/151830; (2018); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

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 1003-21-0 as follows. SDS of cas: 1003-21-0

5-Bromo-1-methyl-1H-imidazole (6.66 g, 41.4 mmol) was added to a round bottom flask followed by tetrahydrofuran (150 mL) under an N2 atmosphere. The contents were cooled to 0 C. in an ice water bath. EtMgBr (3.0 M solution in THF, 13.3 mL, 39.8 mmol) was added slowly via syringe over approximately 5 minutes, then the ice bath was removed and the contents allowed to warm and stirred at room temperature for approximately 30 minutes. The vessel was then re-cooled to 0 C. and a solution of N-methoxy-N-methylpyrimidine-2-carboxamide (3.09 g, 15.9 mmol, Intermediate 66: step a) in THF (20 mL) was cannulated into the reaction vessel. The contents were allowed to stir at 0 C., then slowly warmed to room temperature, then heated to 40 C. in an oil bath for approximately 36 hours. The contents were then cooled to 0 C., quenched with a saturated aqueous NH4Cl solution, diluted with ethyl acetate and transferred to a separatory funnel. The aqueous layer was separated, extracted twice with EtOAc, then the combined organic phases were dried over MgSO4, filtered, then distilled under reduced pressure to yield an amber oil. The crude product was purified by flash column chromatography (silica gel, 0-10% DCM/(10% of a 2 M NH3 MeOH in DCM)) to provide the title compound.

According to the analysis of related databases, 1003-21-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Janssen Pharmaceutica NV; Leonard, Kristi A.; Barbay, Kent; Edwards, James P.; Kreutter, Kevin D.; Kummer, David A.; Maharoof, Umar; Nishimura, Rachel; Urbanski, Maud; Venkatesan, Hariharan; Wang, Aihua; Wolin, Ronald L.; Woods, Craig R.; Fourie, Anne; Xue, Xiaohua; Cummings, Maxwell D.; Jones, William Moore; Goldberg, Steven; US2015/105366; (2015); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

These common heterocyclic compound, 32673-41-9, name is 4-Imidazolemethanol hydrochloride, 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. Safety of 4-Imidazolemethanol hydrochloride

C. By hydrolysis of the esters obtained by the Friedel-Crafts reaction. 2-hydroxy-3-[(1H-imidazol-4-yl)methyl]-benzoic acid and 2-hydroxy-5-[(1H-imidazol-4-yl)methyl]-benzoic acid (hydrochloride). 181 g (1.35 mole) of 1H-imidazole-4-methanol hydrochloride are added in portions to a mixture of 156 ml (1.2 mole) of methyl 2-hydroxybenzoate and 675 g of polyphosphoric acid heated to 80 C. The reaction mixture is maintained with good stirring at this temperature for 288 hours. The mixture is then decomposed on ice, and extracted twice with toluene. The aqueous phase is alkalinized to pH 9.5 by the addition of 790 ml of a saturated aqueous solution of sodium hydroxide. The mineral salts which precipitate are removed by filtration and washed with methanol. The methanolic washing solution is added to the aqueous phase and the resulting mixture is concentrated with partial elimination of the methanol. The solution is then alkalinized to pH 10.3 by addition of a 10N aqueous solution of sodium hydroxide, and is heated at 100 C. for one hour and a half so as to saponify the esters. The aqueous solution is neutralized to pH 7.5 by addition of 10 N hydrochloric acid, filtered on Norit (activated carbon) and the filtrate is evaporated under reduced pressure. The residue is taken up three times in succession in a toluene-ethanol mixture and dried by azeotropic distillation. It is then partially dissolved in hot methanol and the insoluble mineral salts are removed by filtration. The filtrate is evaporated under reduced pressure, the residue is redissolved in a minimum of water, and purification is then carried out by passing through a column of Amberlite IR93 (height of the column: 60 cm; diameter: 8 cm; equivalence: 2.64 mole). Excess 1H-imidazole-4-methanol, together with its polymers, are eluted with water (the pH of the elude varies from 11.2 to 7.3). The elution is then continued with a 4% aqueous solution of hydrochloric acid. The acid elude (9 liters) is adjusted to pH 7.7 by addition of a saturated agueous solution of sodium hydroxide and is then evaporated under reduced pressure. The residue thus obtained is once again dried by azeotropic distillation with a toluene-ethanol mixture, and is then taken up in 1.6 liter of acetonitrile. It is then filtered. The residue on the filter (129 g) is chromatographed on silica (800 g, 15 mum) after having been previously deposited on 300 g of silica (0.2 to 0.5 mm) (eluent: 75:25 v/v ethyl acetate-ethanol). 5.99 g of 2-hydroxy-3-[(1H-imidazol-4-yl)methyl]-benzoic acid is thus obtained. M.P.: 245-252 C. (water). At the same time, 31 g of 2-hydroxy-5-[(1H-imidazol-4-yl)methyl]-benzoic acid are obtained.

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

Reference:
Patent; U C B Societe Anonyme; US4923865; (1990); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

496-46-8, name is Tetrahydroimidazo[4,5-d]imidazole-2,5(1H,3H)-dione, 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. HPLC of Formula: C4H6N4O2

Synthesis of cucurbit[n]urils in hydrochloric acid using paraformaldehyde Unsubstituted glycoluril (20 g) and hydrochloric acid (37 % w/v, 30 mL) were placed in a reaction flask and heated to 90C. Paraformaldehyde (8.87 g) was added in portion-wise and the reaction mixture was then heated to 100 C (internal) for 18 hours. The reaction mixture was cooled and added to methanol (150 mL) to produce a beige powder which was analysed by1H NMR.Approximate Yields by1H NMR (% of recovered product) cucurbit[5]uril 8%, cucurbit[6]uril 44%, cucurbit[7]uril 28%, cucurbit[8]uril 18%, cucurbit[9]uril 0%, cucurbit[10]uril 0% cucurbit[11]uril 0%.Residual formaldehyde by HPLC method was 682 ppm.

The synthetic route of 496-46-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; AQDOT LIMITED; COULSTON, Roger; DIEC, David; NOGUEIRA, Guilherme; GERARDUS DE ROOIJ, Johannes; (23 pag.)WO2018/115822; (2018); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 4238-71-5, 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. 4238-71-5 name is 1-Benzyl-1H-imidazole, 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 a mixture of acetylene 2 (127 mg, 1 mmol) and S (32 mg, 1 mmol) was added 1-methylimidazole (1a; 82 mg, 1 mmol). The mixture was stirred at 20-25 C for 24 h. Column chromatography afforded thione 3a (132 mg, 67%), 4.3.7 (Z)-3-(3-Benzyl-2-thioxo-2,3-dihydro-1H-imidazol-1-yl)-3-phenyl-2-propenenitrile (3e) Analogously, from acetylene 2 (64.0 mg, 0.5 mmol), S (16.0 mg, 0.5 mmol), and 1-benzylimidazole (1e; 79.0 mg, 0.5 mmol) in MeCN (1 mL) (20-25 C, 24 h) thione 3e (27 mg, 96%) was obtained as a light-yellow microcrystalline powder, mp 129-131 C (washed with ether). Initial imidazole 1e was recovered (65 mg, conversion was 18%). 1H NMR (400.13 MHz, CDCl3): delta=7.50-7.30 [m, 10H, Ho,m,p from C(6)-Ph and Ph from N-Bn], 6.74 (s, 2H, 4-H, 5-H), 6.06 (s, 1H, 7-H), 5.27 (s, 2H, CH2 from N-Bn) ppm. 13C NMR (100.62 MHz, CDCl3): delta=164.7 (C-2), 154.1 (C-6), 135.2 (Ci, Ph from N-Bn), 132.4 [Ci from C(6)-Ph], 131.8 [Cp from C(6)-Ph], 129.1 [Cm from C(6)-Ph], 128.9 (Cm, Ph from N-Bn), 128.2 (Cp, Ph from N-Bn), 128.1 (Co, Ph from N-Bn), 126.7 [Co from C(6)-Ph], 118.3 (C-4), 117.1 (C-5), 114.5 (CN), 97.2 (C-7), 51.3 (CH2 from N-Bn) ppm. IR (KBr): 2221 (CN), 1621 (C=C), 1398 (C=S) cm-1. Anal. Calcd for C19H15N3S (317.41): C, 71.90; H, 4.76; N, 13.24; S, 10.10. Found: C, 71.67; H, 4.85; N, 12.92; S, 9.84.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1-Benzyl-1H-imidazole, and friends who are interested can also refer to it.

Reference:
Article; Belyaeva, Kseniya V.; Andriyankova, Ludmila V.; Nikitina, Lina P.; Mal’Kina, Anastasiya G.; Afonin, Andrei V.; Ushakov, Igor A.; Bagryanskaya, Irina Yu.; Trofimov, Boris A.; Tetrahedron; vol. 70; 5; (2014); p. 1091 – 1098;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 3314-30-5, 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. 3314-30-5, name is 1H-Benzo[d]imidazole-2-carbaldehyde, This compound has unique chemical properties. The synthetic route is as follows.

Adding clinfloxacin (500 mg, 1.37 mmol) to a 150 mL round bottom flask,Diethyl phosphite (451.28 mg, 4.10 mmol), benzimidazole-2-carbaldehyde (299.40 mg, 2.05 mmol) and toluene (50 mL) were stirred and refluxed at 120 C for 6 hours, and thin layer chromatography was followed until the reaction was completed. . After concentration, extraction, column chromatography separation,After recrystallization, drying, etc., the compound I-11 is obtained.(297.46 mg). Yield: 34.4%; yellow powder;

The chemical industry reduces the impact on the environment during synthesis 1H-Benzo[d]imidazole-2-carbaldehyde. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Southwest University; Zhou Chenghe; Wang Liangliang; Xu Jiahe; Zhao Wenhao; Ba Tini·nasaiya; (19 pag.)CN110041368; (2019); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 17289-26-8,Some common heterocyclic compound, 17289-26-8, name is 1-Methyl-1H-imidazole-4-carbaldehyde, molecular formula is C5H6N2O, 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 sealed tube is charged with tert-butyl 4-(p-tolylsulfonylhydrazono)- piperidine-1-carboxylate (1284.79 mg; 3.50 mmol; 1 .10 eq.), CS2CO3 (1553.44 mg; 4.77 mmol; 1 .50 eq.). The tube is RM is sealed, purged with argone and then 1 ,4-dioxane (12.00 mL) and 1 -methyl-1 – -imidazole-4- carbaldehyde (350.00 mg; 3.18 mmol; 1.00 eqf.) are added. RM is heated at 1 10C for 48 h. After this time, the mixture is filtered through a Celite pad and then the solvent is evaporated. Crude product is purified by FCC (hexane/EtOAc; gradient) to afford 4-(1 -methyl-1 H-imidazole-4-carbonyl)- piperidine-1 -carboxylic acid tert-butyl ester (483.90 mg; yield 51.0 %; 98% by UPLC) as a beige solid

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1-Methyl-1H-imidazole-4-carbaldehyde, its application will become more common.

Reference:
Patent; SELVITA S.A.; FABRITIUS, Charles-Henry Robert Yves; NOWAK, Mateusz Oktawian; WIKLIK, Katarzyna Anna; SABINIARZ, Aleksandra Barbara; BIE?, Marcin Dominik; BUDA, Anna Ma?gorzata; GUZIK, Pawel Szczepan; JAKUBIEC, Krzysztof Roman; MACIUSZEK, Monika; KWIECI?SKA, Katarzyna; TOMCZYK, Mateusz Micha?; GA??ZOWSKI, Micha? Miko?aj; GONDELA, Andrzej; DUDEK, ?ukasz Piotr; (681 pag.)WO2016/180536; (2016); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

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 312-73-2 as follows. COA of Formula: C8H5F3N2

General procedure: In a typical experimental procedure, a dry, two-necked, 50 mL round bottomed flask was charged with 5 mL of dry MeCN, 1.0 mmol of benzimidazole derivatives and 1.0 mmol of NaH. The solution was stirred at room temperature for 30 min, then a solution of 2,2,2-trifluoro acetimidoyl chloride derivatives (1.0 mmol in 2 mL of dry MeCN) was added dropwise via a syringe. The mixture was stirred at room temperature appropriate time and then filtered. After removing the solvent under reduced pressure, the crude product was purified by preparative thin-layer chromatography on silica gel [eluent: n-hexane/EtOAC, 3:1] to give the products. The products obtained from 2-mercapto benzimidazole and 2-mercapto-1-methyl imidazole were purified by washing with n-hexane.

According to the analysis of related databases, 312-73-2, the application of this compound in the production field has become more and more popular.

Reference:
Article; Darehkordi, Ali; Rahmani, Fariba; Journal of Fluorine Chemistry; vol. 190; (2016); p. 41 – 47;,
Imidazole – Wikipedia,
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. 71759-89-2, name is 5-Iodo-1H-imidazole, A new synthetic method of this compound is introduced below., Product Details of 71759-89-2

4-iodo-1H-imidazole (Compound 13, manufactured by Wako Pure Chemical Industries, Ltd.) (1.9 g, 10 mmol) was dissolved in dichloromethane (40 mL)below freezing,Triethylamine (2.1 mL, 15 mmol),Trityl chloride (3.4 g, 12 mmol) was added,Under an argon gas atmosphere,And the mixture was stirred at room temperature (25 C.) for 17 hours.After completion of the reaction,Add water,Extraction was carried out twice with dichloromethane.The combined dichloromethane layer was dried over anhydrous sodium sulfate, concentrated under reduced pressure,The obtained crude product was purified by silica gel column chromatography (eluent (volume ratio): chloroform / n-hexane = 1/1 ? chloroform) to obtain Compound 14 (4.1 g, 9.3 mmol, yield 93%).

The synthetic route of 71759-89-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NIHON MEDI-PHYSICS COMPANY LIMITED; KYOTO UNIVERSITY; OKUMURA, YUKI; IZAWA, AKIHIRO; AKAMA, KEI; KOBASHI, NOBUYA; ABE, TSUTOMU; SAJI, HIDEO; KIMURA, HIROYUKI; (27 pag.)JP2015/110563; (2015); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 6775-40-2, These common heterocyclic compound, 6775-40-2, name is 5-Phenyl-1H-imidazol-2-amine, 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: A mixture of the corresponding 2-amino-4-arylimidazole1 (1.0 mmol), aromatic aldehyde 2 (2.0 mmol) andmalononitrile 12 (1.0 mmol) in 2 mL of 2-propanol was refluxedduring 20-30 min. After cooling, the yellow solid products14 were filtered off and crystallized from iPrOH. 14a:yellow powder, 65%; mp 221-222 C; 1H NMR (200 MHz,DMSO-d6) delta 9.34 (s, 1H, CHazomethine), 8.18 (d, J = 7.3 Hz,2H, Ar), 7.68-7.48 (m, 7H, Ar, C5NH2 ), 7.31-7.10 (m, 8H,Ar), 5.34 (s, 1H, C7H); 13C NMR (125 MHz, DMSO-d6) delta162.4 (3), 149.5 (Cazomethine), 143.8 (C5), 138.3, 135.3, 133.3,133.0, 132.5, 132.1, 130.4, 129.5, 129.4, 128.8, 128.2, 128.1,127.4, 125.8, 117.9 (N), 71.7 (C6), 45.01 (C7); MS (m/z) (%):429 ([M+?], 25), 285 (100), 194 (19), 104 (26), 77 (19), 43 (25);anal. calcd for C28H23N5 (429.53) C, 78.30; H, 5.40; N, 16.31;found: C, 80.25; H, 5.70; N, 13.41.

The synthetic route of 6775-40-2 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Lipson, Victoria V.; Pavlovska, Tetiana L.; Svetlichnaya, Nataliya V.; Poryvai, Anna A.; Gorobets, Nikolay Yu.; Van Der Eycken, Erik V.; Konovalova, Irina S.; Shiskina, Svetlana V.; Borisov, Alexander V.; Musatov, Vladimir I.; Mazepa, Alexander V.; Beilstein Journal of Organic Chemistry; vol. 15; (2019); p. 1032 – 1045;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem