Author: Jessica.F

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. 6160-65-2, name is 1,1′-Thiocarbonyldiimidazole, A new synthetic method of this compound is introduced below., name: 1,1′-Thiocarbonyldiimidazole

REFERENCE SYNTHETIC EXAMPLE 2; Synthesis of methyl l-hydrazinothiocarbonylpiperidine-4- carboxylate; To a solution of methyl isonipecotate (1.0 g, 7.0 mmol) in tetrahydrofuran was added thiocarbonyl diimidazole (1.24 g, 6.98 mmol) at room temperature, and the reaction solution was stirred at room temperature for1.5 hours and then stirred with hydrazine monohydrate(700 mg, 14.0 mmol) for 4 hours. After addition of saturated aqueous sodium chloride, the reaction solution was extracted with ethyl acetate and chloroform, and the extract was dried over anhydrous magnesium sulfate and concentrated to give the desired product (yield 114%) .Morphology: pale yellow solid LC/MS: condition 5, retention time 0.52 (min)LC/MS (ESI+)m/z; 218, [M+l] +

The synthetic route of 6160-65-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NISSAN CHEMICAL INDUSTRIES, LTD.; WO2006/62240; (2006); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 68282-53-1,Some common heterocyclic compound, 68282-53-1, name is 5-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.

Example 2 3-(5-Methyl-3H-imidazol-4-ylmethylene)-4-pyridin-4-yl-1,3-dihydroindol-2-one A mixture of 4-pyridin-4-yl-1,3-dihydroindol-2-one (50 mg, 0.24 mmol), 5-methyl-3H-imidazole-4-carbaldehyde (24.4 mg, 0.24 mmol) and piperidine (1 drop) in ethanol (2 mL) was stirred at room temperature for 2 days. The precipitate which formed was filtered. Crystals which formed in the filtrate were isolated, washed with ethanol and dried to give 7.8 mg of the title compound. 1H NMR (360 MHz, DMSO-d6) delta 13.55 (br s, 1H, NH), 11.13 (br s, 1H, NH), 8.75 (d, J=6.0 Hz, 2H), 7.85 (s, 1H), 7.50 (d, J=6.0 Hz, 2H), 7.27 (t, J=7.7 Hz, 1H), 6.97 (d, J=7.7 Hz, 1H), 6.83 (d, J=7.7 Hz, 1H), 6.76 (s, 1H, H-vinyl), 1.78 (m, 3H, CH3) MS m/z 303 [M++1].

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5-Methyl-1H-imidazole-4-carbaldehyde, its application will become more common.

Reference:
Patent; Tang, Peng Cho; Wei, Chung Chen; Huang, Ping; Cui, Jingrong; US2002/187978; (2002); 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 253453-91-7 as follows. Recommanded Product: 2-Chloro-1-methyl-1H-imidazole

Step C: (2-Chloro-3-methyl-3H-imidazol-4-yl)-(4-chloro-phenyl)-methanone. To a 1-L, three-necked, round-bottomed flask equipped with a magnetic stirrer, nitrogen inlet and an addition funnel was added 2-chloro-1-methyl-1H-imidazole (15 g, 0.128 mol) and THF (250 mL). The reaction mixture was cooled to -78 C. and n-BuLi (2.5 M in hexanes, 54 mL, 0.135 mol) was added. The pale yellow suspension that formed was stirred for 1 h and a solution of 4-chloro-N-methoxy-N-methyl-benzamide (27 g, 0.135 mol) in THF (50 mL) was then added dropwise. After the addition was complete, the cooling bath was removed and the reaction was allowed to warm to rt. The reaction mixture was quenched with satd. aq. NH4Cl (150 mL), transferred to a separatory funnel, and extracted with EtOAc (1.5 L). The organic layer was washed with water, brine and dried over anhydrous Na2SO4. After filtration, the solvents were evaporated under reduced pressure to yield the product as a crystalline solid. Recrystallization from EtOAc-hexanes afforded the desired ketone (31.2 g, 97%) as a white crystalline solid. mp 173-174 C. IR (film): 1639, 1589, 1517, 1395, 1377, 1253, 1186, 902, 841, 756, 738, 695, 676 cm-1. 1H NMR (400 MHz, CDCl3): delta7.78 (d, J=8.6 Hz, 2H), 7.44 (s, 1H), 7.44 (d, J=8.6 Hz, 2H), 3.97 (s, 3H). 13C NMR (100 MHz, CDCl3): delta183.3, 140.3, 139.5, 139.2, 136.3, 131.2, 130.4, 128.9, 33.5. HRMS (EI): m/z calcd for C11H9Cl2N2O [M+H]+, 255.0092; found, 255.0104. Anal. Calcd for C11H8Cl2N2O: C, 51.8; H, 3.06; N, 10.93. Found: C, 52.08; H, 3.16; N, 10.90. .This step is alternatively performed using 4-chlorobenzoyl chloride-in place of 4-chloro-N-methoxy-N-methyl-benzamide

According to the analysis of related databases, 253453-91-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Jones, Todd K.; Mani, Neelakandha; US2005/250948; (2005); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 113775-47-6, name is Dexmedetomidine, 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 113775-47-6, name: Dexmedetomidine

A mixture of (+)-(S)-4-[1-(2,3-dimethyl-phenyl)-ethyl]-1H-imidazole (dexmeditomidine; 2.00 g, 10.0 mmol) prepared as described in Cordi et al., Synth. Comm. 26: 1585 (1996), in THF (45 mL) and water (40 mL) was treated with NaHCO3 (8.4 g, 100 mmol) and phenylchlorothionoformate (3.7 mL, 27.4 mmol). After stirring for four hours at room temperature, the mixture was diluted with water (30 mL) and ether (75 mL). The organic layer was removed, and the aqueous layer extracted twice with a 50 ml volume of ether. The organic layers were dried over MgSO4 and filtered. The residue was concentrated under vacuum, diluted with MeOH (54 mL) and reacted with NEt3 (6.5 mL) at room temperature for 16 hours. The solvent was removed under vacuum and replaced with 30% CH2C12:hexane. The solvent was removed again and solids formed. After further resuspension in 30% CH2C12:hexane, the solid was collected on a filter, washed with CH2C12:hexane and dried under vacuum to give Compound 1 ((+)-(S)-4-[1-(2,3-dimethyl-phenyl)-ethyl]-1,3-dihydro-imidazole-2-thione) 1.23 g (53%). A schematic of the preparation of Compound 1 is shown above. Characterization of the product yielded the following. Optical rotation: [a]D20+14 (c 1.25 in MeOH). 1H NMR: (300 MHz, DMSO) d 11.8 (s, 1H), 11.6 (s, 1H), 7.03-7.01 (m, 2H), 6.95-6.91 (m, 1H), 6.50 (s, 1H), 4.15 (q, J=6.9 Hz, 1H), 2.25 (s, 3H), 2.20 (s, 3H), 1.38 (d, J=6.9 Hz, 3H).

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

Reference:
Patent; Allergan, Inc.; US2005/59721; (2005); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 33016-47-6, 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. 33016-47-6, name is 1-Trityl-1H-imidazole-4-carbaldehyde belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

A suspension of 2a (0.50 g, 1.48 mmol), propyl triphenylphosphonium bromide (0.63 g, 1.63 mmol) and NaH (powered 95%, 0.05 g, 2.22 mmol) in anhydrous THF (8 mL), was stirred at rt for 8 h under Ar atmosphere. Then, the reaction mixture was quenched with saturated aqueous NaHCO3 (5 mL) solution and extracted with CH2Cl2 (3 × 15 mL). The organic layer was washed with H2O (1 × 10 mL), dried over Na2SO4 and concentrated in vacuo. The residue was purified by flash column chromatography (silica gel, EtOAc/Hex 1:1) to furnish the Z-3 isomer (0.44 g) which is the sole isolated product. Yield: 81%; Rf 0.63 (EtOAc/Hex 4:1); tR 12.42 min (30% MeCN ? 100% MeCN in 30 min); ESI-MS (m/z): 123.18 [M + H], 243.26 [Tr]; 1H NMR (400 MHz, CDCl3): delta 7.64 (br s, 1H), 7.36-7.35 (m, 9H), 7.16-7.13 (m, 6H), 6.75 (br s, 1H), 6.25 (dt, 1H, J = 1.5, 11.6 Hz), 5.60 (dt, 1H, J = 7.5, 11.6 Hz), 2.28 (quint d, 2H, J = 1.7, 7.5 Hz), 1.00 (t, 3H, J = 7.5 Hz); 13C NMR (160 MHz, CDCl3): delta 141.70, 137.64, 137.15, 134.53, 129.66, 128.29, 128.18, 120.20, 119.00, 76.03, 22.55, 13.79.

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

Reference:
Article; Agelis, George; Resvani, Amalia; Koukoulitsa, Catherine; Tumova, Tereza; Slaninova, Jirina; Kalavrizioti, Dimitra; Spyridaki, Katerina; Afantitis, Antreas; Melagraki, Georgia; Siafaka, Athanasia; Gkini, Eleni; Megariotis, Grigorios; Grdadolnik, Simona Golic; Papadopoulos, Manthos G.; Vlahakos, Demetrios; Maragoudakis, Michael; Liapakis, George; Mavromoustakos, Thomas; Matsoukas, John; European Journal of Medicinal Chemistry; vol. 62; (2013); p. 352 – 370;,
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. 693-98-1, name is 2-Methyl-1H-imidazole, A new synthetic method of this compound is introduced below., Quality Control of 2-Methyl-1H-imidazole

General procedure: Compounds 1-18 were synthesized using the following generalprocedure reported by Salvio et al. [41]. A mixture of potassium carbonate(2.0 g, 14.4 mmol), imidazole derivatives 27-28 (32.9 mmol)and compounds 29-37 (4.7 mmol) in dry acetonitrile (50 ml) was heatedunder reflux and the progress of the reaction was monitored byTLC. Then the solvent was evaporated under the vacuum and the residuewas dissolved in DCM (100 ml) *. The organic layer was washedwith saturated sodium bicarbonate aqueous solution (2×50 ml),passed through diatomaceous earth, dried over sodium sulfate, evaporatedunder the vacuum, and purified by flash column chromatography(ethyl acetate-hexane 0-100%)** to give the products 1-18.*Note 1: Ethyl acetate (200 ml) was used for compounds 17 and 18.**Note 2: Compounds 17 and 18 (ethyl acetate-methanol 0-100%).

The synthetic route of 693-98-1 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Khalili Arjomandi, Omid; Kavoosi, Mahboubeh; Adibi, Hadi; Bioorganic Chemistry; vol. 92; (2019);,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature 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.

General procedure: Bis-vinylimidazolium bromoethane ([CnDVIM]Br) were synthesized by the reaction between 1-vinylimidazole and (CH2)2Br2, (CH2)4Br2, or (CH2)8Br2 [20]. Typically, 1-vinylimidazole (4.20g, 44.6mmol) and (CH2)nBr2 (21.7mmol) were dissolved in 5.0mL methanol. Then, the mixture was continuously magnetic stirred for 5min to get a homogenous solution and poured into a 50mL single-necked flask. After aerated nitrogen for about 3min, the flask was sealed and placed into 65C oil bath with a continuously magnetic stirring for 24h. After cooling to room temperature, excess diethyl ether (200mL) was poured into the solution and the crude salt was obtained. The obtained salt was washed with diethyl ether three times and dried under vacuum to get the yellow [CnDVIM]Br.

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

Reference:
Article; Liu, Yang; Zhao, Jia; He, Fang; Zheng, Chen; Zhao, Xiaopeng; Yin, Jianbo; Polymer; vol. 171; (2019); p. 161 – 172;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

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. 496-46-8, name is Tetrahydroimidazo[4,5-d]imidazole-2,5(1H,3H)-dione, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: Tetrahydroimidazo[4,5-d]imidazole-2,5(1H,3H)-dione

The tetrol derivative (compound 2.6) of 3a, 6a- cyclopentanoglycoluril (1 g, 3.3 mmol) was added to a solution of unsubstituted glycoluril (937 mg, 6.6 mmol) in conc. HCL (2 mL) and the mixture stirred at room temperature for 30 min. The homogeneous mixture was poured into MEOH (10 mL) and the precipitate collected and dried to give predominantly the trimer.

According to the analysis of related databases, 496-46-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; UNISEARCH LIMITED; WO2005/26168; (2005); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 72-40-2,Some common heterocyclic compound, 72-40-2, name is 5-Amino-1H-imidazole-4-carboxamide hydrochloride, molecular formula is C4H7ClN4O, 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.

4-amino-5-imidazolecarboxamide hydrochloride was heated to reflux in phosphorus oxychloride for 3.5 hs and after purification gave 4-amino-5-nitrile imidazole. This was resuspended in ethanol saturated with HCl overnight and purification gave 4-amino-5-ethylimino ester imidazole hydrochloride. This was combined with diphenylborinic acid ethanolamine ester in tetrahydrofuran (THF) overnight to yield the title compound.

The synthetic route of 72-40-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Benkovic, Stephen J.; Shapiro, Lucy; Wright, Rachel; Stephens, Craig; Kahng, Lyn Sue; Berdis, Anthony; Lee, Irene; US2005/227933; (2005); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Some common heterocyclic compound, 41716-18-1, name is 1-Methyl-1H-imidazole-4-carboxylic acid, molecular formula is C5H6N2O2, 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. category: imidazoles-derivatives

To a suspension of [1-METHYL-IMIDAZOLE-4-CARBOXYLIC ACID (11.] 4g, 90 [MMOL)] in THF (500ml) at [0°C,] was added drop-wise a solution of lithium aluminium hydride [(1 M] in THF, [117ML,] 117 [MMOL)] and the mixture was stirred at room temperature overnight and then at [50°C] for 1 hour Water (3 [ML)] was added followed by [NA2SO4] and the mixture was filtered through [CELITETM.] The filtrate was concentrated under reduced pressure to afford the title compound as a solid [(8G,] 78.95percent) ;’H NMR (300 MHz, [CDCI3)] 6 ppm: 7.25 (s, 1 H), 6. 7 (s, 1H), 5.25 (m, 1H), 4.4 (s, 2H), 3.45 (s, 3H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 41716-18-1, its application will become more common.

Reference:
Patent; SMITHKLINE BEECHAM CORPORATION; WO2004/13138; (2004); A2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem