Imidazoles-derivatives

Synthetic Route of 570-22-9, These common heterocyclic compound, 570-22-9, name is 1H-Imidazole-4,5-dicarboxylic acid, 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.

REFERENCE EXAMPLE 13 4,5-Bis(ethoxycarbonyl)imidazole A mixture of 4.0 g (25.6 mmols) of imidazole-4,5-dicarboxylic acid, 600 ml of ethanol and 16 ml of conc. sulfuric acid was heated under reflux for 7 hours. After cooling to 0 C., the mixture was neutralized with a 2 normal aqueous sodium hydroxide solution. The solvent was evaporated under reduced pressure, and then water was added to the residue followed by extraction of the solution with chloroform. The chloroform layer was washed with an aqueous saturated sodium bicarbonate solution and then with an aqueous saturated sodium chloride solution and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the residue was dried to afford 2.5 g (yield: 46%) of the title compound. NMR (CDCl3) delta (ppm): 7.83(1H, s), 7.26(1H, s), 4.41 (4H, q, J=7.2 Hz), 1.38(6H, t, J=7.2 Hz)

The synthetic route of 570-22-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Kyowa Hakko Kogyo Co., Ltd.; US5053408; (1991); A;,
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Reference of 1072-63-5, 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. 1072-63-5, name is 1-Vinyl-1H-imidazole belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

Comprising the steps of: 0.840 g of alpha-mercaptomethyltrimethoxysilane prepared in Example 6 and 1.176 g of 1-Vinylimidazole were placed in a round bottom flask wrapped in aluminum box paper. Then, 8 mL of tetrahydrofuran was added, and after mixing uniformly, 0.076 g of benzoin dimethyl ether was added, the mixture was uniformly stirred, the aluminum box paper was removed, and irradiated at room temperature for 30 minutes under a UV lamp having a power of 20 W and a wavelength of 365 nm. After the completion of the reaction, the solvent was distilled off under reduced pressure, and the degree of vacuum was 5 to 6 mmHg, which was precipitated three times in n-hexane, and dried under vacuum at 40 C to a constant weight to obtain alpha-(1-ethylimidazolyl)mercaptomethyltrimethoxysilane, purity 96%, yield 96%. The infrared spectrum of the product alpha-(1-ethylimidazolyl)mercaptomethyltrimethoxysilane obtained in this example is shown in Fig. 19, and the nuclear magnetic resonance spectrum is shown in Fig. 20. 19 and 20, the product obtained in this example was alpha-(1-ethylimidazolyl)mercaptomethyltrimethoxysilane

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

Reference:
Patent; Shandong University; Bei Yiling; Gao Yanhong; Zhu Qingzeng; Feng Shengyu; (24 pag.)CN109053794; (2018); A;,
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Imidazole | C3H4N2 – PubChem

Application of 641571-13-3,Some common heterocyclic compound, 641571-13-3, name is 3-(4-Methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)benzoic acid, molecular formula is C12H9F3N2O2, 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.

To a solution of the carboxylic acid 6m (1.0g, 3.91 mmol) in DMF (18mL), HOBt (0.59g, 4.69 mmol) and EDC (0.82mL, 4.69 mmol) was added 4-methyl-3-nitroaniline (0.71 g, 4.69 mmol) and the mixture was stirred at 25 C for 12 hours. The reaction mixture was concentrated under reduced pressure, redissolved in EtOAc and extracted with 0.5 M NaHCO3 and water. The organic phase was dried over MgSO4, concentrated under reduced pressure and the resulting solid was washed with DCM and hexane affording the desired amide in pure form (1.01g, 64% yield). IR (neat): upsilon? = 3344, 1682, 1654, 1603, 1537, 1524, 1498, 1448, 1407, 1305, 1283, 1255, 1172, 1121, 1103, 1079, 1001, 904, 877, 829, 812, 751, 739, 690, 671, 617, 503, 418 cm-1; MS (ESI), m/z: calcd for C19H16F3N4O3+, 405.11690; found, 405.11716.

The synthetic route of 641571-13-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Universitaet Zuerich; Unzue Lopez, Andrea; Dong, Jing; Lafleur, Karine Anne; Zhao, Hongtao; Frugier, Emilie; Caflisch, Amedeo; Nevado Blazquez, Cristina; EP2924039; (2015); A1;,
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Imidazole | C3H4N2 – PubChem

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;,
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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;,
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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;,
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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