Month: December 2020

Application of 937013-66-6, The chemical industry reduces the impact on the environment during synthesis 937013-66-6, name is 2-(3-Bromophenyl)-1H-imidazole, I believe this compound will play a more active role in future production and life.

General procedure: A mixture of 4-bromobenzaldehyde (2.78 g; 15.0 mmol), [3-(aminocarbonyl)-phenyl]boronic acid (2.72 g; 16.5 mmol), PdCl2(dppf).CH2Cl2(0.306 g; 0.38 mmol), DME (25 mL) and Na2CO3(25 mL of a 2M solution) was sparged 20 min with N2and heated under reflux for 90 min (consumption of aryl bromide observed by LC/MS). Upon cooling, the mixture was partitioned between EtOAc/H2O, layers were separated, and the aqueous layer was extracted with EtOAc (¡Á2). Combined organics were washed (H2O, brine), dried over Na2SO4and concentrated in vacuo. The residue was purified by flash chromatography (EtOAc/hexanes), affording the title compound as a tan solid. Used IV-21 and 4- formylphenyl boronic acid Note 1, 2. Note 1 Used 4:1 v/v PhMe/EtOH as organic cosolvents (instead of DME).Note 2 Used Pd(PPh3)4as catalyst (instead of PdCl2(dppf).CH2Cl2).

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, 2-(3-Bromophenyl)-1H-imidazole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; SMITHKLINE BEECHAM CORP; COWAN, D. J; LARKIN, A. L.; ZHANG, CUNYU; MUSSO, D. L.; GREEN, G. M.; CADILLA, R.; SPEARING, P.K.; BISHOP, M. J.; SPEAKE, J. D.; (219 pag.)CN102516115; (2016); B;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

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. Safety of 5-Phenyl-1H-imidazol-2-amine

General procedure: The (5-benzoyl-1-methyl-1H-pyrrol-2-yl)acetic acid (6)(1 mmol) was dissolved in dry DMF. To this TBTU (2mmol) was added and stirred for 30 min under nitrogenatmosphere. Then 4-aryloxazol-2-amine (7)/4-arylthiazol-2-amine (8)/4-aryl-1H-imidazol-2-amine (9) (1 mmol) followedby DIPEA (0.5 ml) were added and the reactionmixture was heated at 50 C for 6 h. After completion ofreaction (progress of reaction was monitored by TLC) thecontents were allowed to cool and poured into ice water.The resultant solid was filtered, dried and recrystallizedfrom 2-propanol.

The synthetic route of 5-Phenyl-1H-imidazol-2-amine has been constantly updated, and we look forward to future research findings.

Reference:
Article; Sowmya, Donthamsetty V.; Basha, Shaik Sharafuddin; Devi, Palampalli Uma Maheswari; Lavanyalatha, Yerraguravagari; Padmaja, Adivireddy; Padmavathi, Venkatapuram; Medicinal Chemistry Research; vol. 26; 5; (2017); p. 1010 – 1021;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 492-98-8, 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. 492-98-8, name is 1H,1’H-2,2′-Biimidazole belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

Example 16: Synthesis of (tetrakis(2-phenylpyridinato)(mu-biimidazolyl) diiridium(III), Abbreviation; [Ir(ppy)2BIm]2) [0307] [0308] Under argon atmosphere, into a 100 mL Schlenk flask equipped with a stirrer were placed 322 mg (0.30 mmol) of di-mu-chloro-tetrakis(2-phenylpyridinato) diiridium(III), 40 mg (0.30 mmol) of 2,2′-biimidazole and 60 ml of tetrahydrofuran. And then, the mixture was stirred at room temperature for 13 hours. Subsequently, 83 mg (0.63 mmol) of tert-butoxy potassium (t-BuOK (85 wt% product)) was added to the mixture, and the mixture was reacted under stirring at room temperature for 24 hours. After the completion of the reaction, tetrahydrofuran was distilled off under reduced pressure, and then methylene chloride was added to the residue, and the insoluble substance was removed by filtration. The filtrate was concentrated under reduced pressure. The resultant crude reaction product was subjected to column chromatography with alumina (developing solvent: methylene chloride / hexane (volume ratio; 3/1) : 0.5 % triethylamine) for purification, to provide 113 mg of the desired compound as a yellow solid. (Yield: 33 %) The desired compound obtained was a mixture of isomers, and the product ratio was Isomer 1 (main product) : Isomer 2 = 61:39. [0309] Additionally, tetrakis(2-phenylpyridinato)(mu-biimidazolyl) diiridium(III) was a novel compound, which had the following properties: [0310] 1H-NMR (400MHz, C4D8O, delta (ppm)) Isomer 1; 8.18 (dd, 4H), 7.86 (d, 4H), 7.70-7.55 (m, 8H), 6.81-6.72 (m, 8H), 6.66-6.62 (m, 4H), 6.38 (dd, 4H), 6.11 (s, 4H) Isomer 2; 7.92 (d, 4H), 7.78 (dd, 4H), 7.70-7.55 (m, 8H), 6.81-6.72 (m, 8H), 6.66-6.62 (m, 4H), 6.32 (dd, 4H), 6.13 (s, 4H) FD-MS (M/Z): 1132 M+

The synthetic route of 1H,1’H-2,2′-Biimidazole has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Ube Industries, Ltd.; FUJIMURA, Osamu; FUKUNAGA, Kenji; IWASA, Takafumi; TANAKA, Yasuhiro; FUJITA, Harunori; MURAKAMI, Tadashi; HONMA, Takashi; MACHIDA, Toshikazu; KASHIHARA, Natsuko; EP2647642; (2013); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Some common heterocyclic compound, 15965-31-8, name is 5-Chloro-1H-imidazole, molecular formula is C3H3ClN2, 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 5-Chloro-1H-imidazole

2.2. Synthesis of 1-[(4-chloro-lH-imidazol-1-yl) methyl]-4-(3, 4, 5-trifluorophenyl)- pyrrolidin-2-one 72 using thionyl chloride. Alternatively to method 2.1, 1-imidazol-1-ylmethyl-pyrrolidin-2-ones derivatives can also be obtained by a similar reaction of the hydroxymethyl derivative with successively thionyl choride in toluene for 16 h at room temperature followed by quenching of the chloromethyl derivative with an imidazole in the presence of Et3N at room temperature. For example, 1-hydroxymethyl-4- (3, 4,5-trifluoro-phenyl)- pyrrolidin-2-one reacts with thionyl chloride and 4-chloroimidazole to afford 1- [ (4- chloro-lH-imidazol-1-yl) methyl]-4- (3, 4,5-trifluorophenyl)-pyrrolidin-2-one 72 LC/MS (MH+): 330/332.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 15965-31-8, its application will become more common.

Reference:
Patent; UCB, S.A.; WO2005/54188; (2005); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 10364-94-0, These common heterocyclic compound, 10364-94-0, name is (1H-Imidazol-1-yl)(phenyl)methanone, 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: To a solution of substrate (100 mg) in 2.5 mL MeCN (dry) was added DBU (0.2 equiv.), and themixture was allowed to stir at 50 C for 10 min. 1-Benzoylimidazole (1.1 equiv.) in MeCN (dry, 0.5 mL)was added to the reaction mixture in two portions and it was allowed to stir at 50 C for 8 h. MeCNwas removed under reduced pressure and the resulting mixture was purified by flash columnchromatography (ethyl acetate/petroleum ether = 1:6 to 2:1) to afford benzoylated products.

The synthetic route of 10364-94-0 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Lu, Yuchao; Hou, Chenxi; Ren, Jingli; Xin, Xiaoting; Xu, Hengfu; Pei, Yuxin; Dong, Hai; Pei, Zhichao; Molecules; vol. 21; 5; (2016);,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 24155-42-8,Some common heterocyclic compound, 24155-42-8, name is 1-(2,4-Dichlorophenyl)-2-(1H-imidazol-1-yl)ethanol, molecular formula is C11H10Cl2N2O, 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: R- (-) -1- (2,4-dichlorophenyl) -2- (lH-imidazol-1- yl) -ethanol (VI); To a solution of 5 g of 1- (2, 4-dichlorophenyl) -2- (IH- imidazol-1-yl) -ethanol (II) in a mixture of acetone- methanol, 3.21 g of D-tartaric acid dissolved in a mixture of acetone-methanol were added at room temperature. Once the addition was completed, the mixture was stirred for further 30 minutes at room temperature. The resultant solid was filtered and crystallized from methanol. A mixture consisting of the resulting salt, water and methylene chloride was treated with a concentrated solution of sodium hydroxide. The organic layer was washed with water and concentrated at reduced pressure to yield 1.85 g (37%) of (VI) whose enantiomeric purity was higher than 98% in R- {-) isomer.

The synthetic route of 24155-42-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; FERRER INTERNACIONAL, S.A.; WO2006/29811; (2006); A1;,
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. 33529-02-1, name is 1-Decyl-1H-imidazole, A new synthetic method of this compound is introduced below., Application In Synthesis of 1-Decyl-1H-imidazole

In a necked 50 ml equipped with acondenser, 4.9 ml (57 mmol) of allyl bromide areadded dropwise to 0.01 mol of 1a(2.92g) or 1b(2.08g) in room temperature and free solventconditions. The reaction mixture is refluxed andstirred until a solid slightly pasty appears. Thisresidue is triturated with ether and then filteredunder vacuum to obtain a solid dough.

The synthetic route of 33529-02-1 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Djellal, Ahmed; Amirat, Samia; Oriental Journal of Chemistry; vol. 31; 4; (2015); p. 2391 – 2394;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 3034-50-2, 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 3034-50-2 as follows.

A. 1-Trityl-4-carboxaldehyde-1H-imidazole (cas No.33016-47-6) According to procedure outlined in J. Med. Chem. 2002, 45(1), 177, to imidazole-4-carboxaldehyde (15.0 g, 156.2 mmol) in DMF (300 mL) is added triethylamine (43.8 ml, 312 mmol) followed by trityl chloride (44.4 g, 159.0 mmol). The reaction mixture is stirred at ambient temperature for 18 h before the solvent is removed in vacuo. The resulting solid is dissolved in dichloromethane and washed with sodium bicarbonate and water. The organic phase is concentrated in vacuo to give the desired material as a solid.

According to the analysis of related databases, 3034-50-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Ksander, Gary Michael; Meredith, Erik; Monovich, Lauren G.; Papillon, Julien; Firooznia, Fariborz; Hu, Qi-Ying; US2007/49616; (2007); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 37067-95-1, A common heterocyclic compound, 37067-95-1, name is 2-Iodo-1-methyl-1H-imidazole, molecular formula is C4H5IN2, 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.

b) Synthesis of N1-methyl-N1-(1-methyl-1H-imidazol-2-yl)ethane-1,2-diamine A mixture of 4.8 g (23.0 mmol) 2-iodine-1-methyl-imidazol, 12.2 ml (138.0 mmol) N-methyl-ethylene-diamine, 80 mg (1.3 mmol) copper and 374 mg (3.8 mmol) copper(I) chloride was heated for 1 h to 70 C. erhitzt. After cooling to RT, the solution was received with brine and DCM and the phases were separated. The organic phase was dried over MgSO4, filtered and concentrated in a vacuum. CC (DCE/EtOH/conc. aq. NH4OH sol. 5:1:0.06) was performed with the residue, whereby 215 mg (1.4 mmol, 6%) N1-methyl-N1-(1-methyl-1H-imidazol-2-yl)ethane-1,2-diamine was obtained.

The synthetic route of 37067-95-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Grunenthal GmbH; US2008/261996; (2008); A1;,
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. 10351-75-4, name is 1H-Benzo[d]imidazole-5,6-dicarboxylic acid, A new synthetic method of this compound is introduced below., Formula: C9H6N2O4

2.2.2 H23-DPBB The above mentioned synthesis procedure was repeated except 3-aminobenzoic acid was used. Yield: 65.5%. Element analysis (%): Anal. Calc. C16H9N3O4: C 62.54, H 2.95, N 13.68. Found: C 62.60, H 2.92, N 13.69%. IR (KBr pellet, cm-1): 3310(m), 2520(m), 1780(vs), 1670(vs), 1600(m), 1550(m), 1480(vs), 1090(vs), 840(m), 776(m), 673(s), 543(s). Negative ESI-MS (m/z): 305.88 (H23-DPBB-H+). 1H NMR (DMSO-d6): delta: 7.669 (J = 1.6 Hz, t, 1H, Ph-H), 7.747 (J = 7.2 Hz, d, 1H, Ph-H), 7.995 (J = 8.0 Hz, d, 1H, Ph-H) 8.057 (s,1H, Ph-H) 8.104 (s, 1H, Ph-H) 8.201 (s, 1H, Ph-H), 8.596 (s, 1H, Im-H), 13.293 (s, 1H, COOH). Melting points: above 300 C.

The synthetic route of 10351-75-4 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Yang, Jing-Si; Zhu, Jiang; Liu, Rui-Bin; Ni, Jun; Chang, Zhi-Duo; Hu, Tao; Zhang, Jian-Jun; Meng, Chang-Gong; Inorganica Chimica Acta; vol. 394; (2013); p. 117 – 126;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem