Tag: M.W=100-200

Reference of 6160-65-2,Some common heterocyclic compound, 6160-65-2, name is 1,1′-Thiocarbonyldiimidazole, molecular formula is C7H6N4S, 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.

Under the protection of argon, the cross spore alkali (1.86 g, 4.0 mmol) for 100 ml dichloromethane dissolved, at room temperature by adding 10 ml triethylamine andN,N’ – Sulfur carbonyl diimidazole (1.3 g, 8.0 mmol), the reaction overnight at room temperature. The reaction solution is poured into 100 ml ice water, dichloromethane extraction, anhydrous sodium sulfate after drying the organic phase concentration, silica gel column chromatography separation, dichloromethane: methanol=20:1 (v/v) elute and get the 3′ -N- (1 – Imidazole sulfur on behalf of the carboxamido) cross spore alkali 1.9 g, yield 82%,

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

Reference:
Patent; Guizhou Chinese Academy Of Sciences Natural Result Chemical Emphasis Experiment Shi (Guizhou Medical University Natural Result Chemical Emphasis Experiment Shi); Wang Liping; Zhu Weiming; Li Mingpeng; Xu Yanchao; Zuo Mingxing; (25 pag.)CN109879888; (2019); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 17325-26-7, name is Methyl 1H-imidazole-5-carboxylate, 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 17325-26-7, Application In Synthesis of Methyl 1H-imidazole-5-carboxylate

Methyl 4-imidazolecarboxylate (1.09 g, 8.62 mmol) was slowly added to a suspension of sodium hydride (60% dispersion in oil, 0.52 g, 13 mmol) in DMF (40 mL). The mixture was heated to 80 C. and stirred at this temperature for 1 hour. A solution of compound 8 (3.61 g, 12.90 mmol) in DMF (20 mL) was added dropwise to the reaction mixture at this temperature and the reaction mixture stirred a further 12 hours at 80 C. The cooled mixture was filtered, the volatiles removed in vacuo and the residue purified by column chromatography on silica gel (100% n-heptane to 100% EtOAc) to yield compound 10 (0.91 g, 34%) as a yellow semi solid first LC-MS (MH+): m/z=311.3, tR (min,)=1.15 then compound 9 (1.38 g, yield: 51%) as a yellow solid LC-MS (MH+): m/z=311.3, tR (minutes)=1.16.

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; H. Lundbeck A/S; US2012/129836; (2012); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 705-09-9,Some common heterocyclic compound, 705-09-9, name is 2-(Difluoromethyl)-1H-benzo[d]imidazole, molecular formula is C8H6F2N2, 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 mixture of 2-difluoromethyl-1H-benzimidazole (72.2 g) (67.0 g, 400 mmol), 2,4-dichloro-6-morpholino-1,3,5-triazine (94.0 g, 400 mmol) and anhydrous potassium carbonate (221.1 g, 1600 mmol) in DMF (1.60 L) was stirred at room temperature for 4 hours. The resulting mixture was poured into water. White precipitates were collected and washed with DMF and then acetone successively. The solid was dried under reduced pressure to give 4-chrolo-2-(2-difluoromethylbenzimidazol-1-yl)-6-morpholino-1,3,5-triazine (131.5 g, 358.6 mmol) as white crystal in 90% yield. MS m/z: 366 (M+) 1H-MNR(CDCl3) delta: 3.80-3.87 (4H, m), 3.94-4.01 (4H, m), 7.38-7.53 (2H, m), 7.58 (1H, t, J=54 Hz), 7.90 (1H, d, J=7 Hz), 8.42 (1H, d, J=7 Hz).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-(Difluoromethyl)-1H-benzo[d]imidazole, its application will become more common.

Reference:
Patent; ZENYAKU KOGYO KABUSHIKI KAISHA; US2007/244110; (2007); 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. Recommanded Product: 32673-41-9

Step A 1-Triphenylmethyl-4-(hydroxymethyl)-imidazole To a solution of 4-(hydroxymethyl)imidazole hydrochloride (35.0 g, 260 mmol) in 250 mL of dry DMF at room temperature was added triethylamine (90.6 mL, 650 mmol). A solid precipitated from the solution. Chlorotriphenylmethane (76.1 g, 273 mmol) in 500 mL of DMF was added dropwise. The reaction mixture was stirred for 20 hours, poured over ice, filtered, and washed with ice water. The resulting product was slurried with cold dioxane, filtered, and dried in vacuo to provide the titled product as a solid which was sufficiently pure for use in the next step.

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

Reference:
Patent; Merck & Co., Inc.; US5852010; (1998); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 3034-38-6, 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. 3034-38-6, name is 5-Nitro-1H-imidazole belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

4-nitroimidazole(1.41 g), potassium carbonate (2.5 g), methyl iodide (1.9 g), and 20 mL of acetonitrile,The reaction was refluxed for 12 h. Spin dry under reduced pressure, add 50mL of water,It was extracted three times with 50 mL of ethyl acetate. The organic layers were combined and washed with saturated brine.The organic phase was dried by adding anhydrous Na2SO4, and dried under reduced pressure.1-methyl-4-nitroimidazole(1.5g).

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

Reference:
Patent; China Pharmaceutical University; Zhang Dayong; Zhang Tiantai; Shu Lei; (27 pag.)CN110330484; (2019); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 705-09-9, These common heterocyclic compound, 705-09-9, name is 2-(Difluoromethyl)-1H-benzo[d]imidazole, 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.

Example 67 (R)-2-(2-(difluoromethyl)-1H-benzo[d]imidazol-1-yl)-5-(4-(methylsulfonyl)benzyl)-5,6,6a,7,9,10-hexahydro-[1,4]oxazino[3,4-h]pteridine A mixture of (R)-2-chloro-5-(4-(methylsulfonyl)benzyl)-5,6,6a,7,9,10-hexahydro-[1,4]oxazino[3,4-h]pteridine (PREPARATION x10 50 mg, 0.127 mmol), 2-(difluoromethyl)-1H-benzo[d]imidazole (21.29 mg, 0.127 mmol), cesium carbonate (61.9 mg, 0.190 mmol), tris(dibenzylideneacetone)dipalladium(0) (4.64 mg, 5.06 mumol) and 2-dicyclohexylphosphino-2′,4′,6′-triisopropyl-1,1′-biphenyl (4.83 mg, 10.13 mumol) in DMF 253 muL was heated to 130 C. in a microwave for 40 minutes. Additional tris(dibenzylideneacetone)dipalladium(0) (4.64 mg, 5.06 mumol) and 2-dicyclohexylphosphino-2′,4′,6′-triisopropyl-1,1′-biphenyl (4.83 mg, 10.13 mumol) were added, and the reaction mixture was heated to 130 C. in a microwave for 1 hour. EtOAc and water were added and the mixture was filtered through Celite and extracted with EtOAc (2*). The combined extracts were washed with brine, dried over Na2SO4, filtered, and concentrated in vacuo. The residue was purified by column chromatography (SiO2-NH2, 30-100% EtOAc/hexane gradient) to afford the title compound as a yellow solid (14.3 mg, 21.4%). 1H NMR (400 MHz, CDCl3) delta 3.08 (s, 3H), 3.19-3.38 (m, 4H), 3.68 (td, J=12.00, 2.78 Hz, 1H), 3.83-3.92 (m, 1H), 3.94-4.02 (m, 1H), 4.11-4.20 (m, 1H), 4.44-4.63 (m, 3H), 7.36-7.75 (m, 6H), 7.93-8.01 (m, 3H), 8.17-8.23 (m, 1H). ESI-MS m/z [M+H]+ calc’d for C25H24F2N6O3S, 527.16. found 527.3.

The synthetic route of 705-09-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; US2012/220575; (2012); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

2849-93-6, name is 1H-Benzimidazole-2-carboxylic acid, 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. Recommanded Product: 1H-Benzimidazole-2-carboxylic acid

1 H-Benzimidazole-2-carboxylic acid (500 mg, 3.08 mmol) was suspended in EtOH (5 ml_), treated with thionyl chloride (1.12 ml_, 15.4 mmol), and heated to reflux overnight. The reaction mixture was concentrated in vacuo, yielding 644 mg (99%) of the crude product. 1H NMR (400 MHz, CD2CI2) delta 1.32 (t, 3H), 4.38 (q, 2H), 7.30 (m, 2H), 7.63 (m, 2H).

The synthetic route of 2849-93-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BAYER PHARMACEUTICALS CORPORATION; WO2006/49681; (2006); A2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 32673-41-9, 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. 32673-41-9, name is 4-Imidazolemethanol hydrochloride, This compound has unique chemical properties. The synthetic route is as follows.

Step 8.a. 4-Hydroxymethyl-1-triphenylmethyl-imidazole 4-Hydroxymethylimidazole hydrochloride (compound xiii where R2 is H) (2.50 g, 18.6 mmol) and Et3N (2.59 ml, 18.6 mmol) were combined in DMF (30 ml) and stirred at room temperature.. A solution of chlorotriphenylmethane (5.19 g, 18.6 mmol) in DMF (25 ml) was added dropwise at room temperature and the resulting mixture was stirred at room temperature for about 23 hours and then poured into ice water (300 ml).. The product was filtered off, washed with cold water (75 ml) and triturated with p-dioxane (30 ml).. The product was filtered off and dried under reduced pressure to yield product (4.96 g, 78%). NMR (300MHZ, DMSO-d6, 30C) 7.3-7.5 (9H, m), 7.25-7.35 (1H, d), 7.0-7.2 (6H, m), 6.7-6.75 (1H, s), 4.15-4.2 (2H, m).

The chemical industry reduces the impact on the environment during synthesis 4-Imidazolemethanol hydrochloride. I believe this compound will play a more active role in future production and life.

Reference:
Patent; SOCIETE DE CONSEILS DE RECHERCHES ET D’APPLICATIONS SCIENTIFIQUES (S.C.R.A.S.); EP1382607; (2004); A2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 98873-55-3,Some common heterocyclic compound, 98873-55-3, name is 2-(1H-Imidazol-1-yl)acetonitrile, molecular formula is C5H5N3, 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 mixture of potassium hydroxide (0.25 g, 4.5 mmol) in 3 ml of dimethylsulfoxide was purged with argon and cooled to 10C. A solution of 2-imidazol-1-ylacetonitrile (13, 0.23 g, 2.2 mmol) and carbon disulfide (0.32 g, 4.3mmol) in 2 ml of dimethylsulfoxide was then slowly added. The cooling bath was removed and the resulting orange mixture was stirred for 15 min at room temperature. A solution of [2-(2,4-dichlorophenyl)-3-methylsulfonyloxy-propyl]methanesulfonate (25, 0.54 g, 1.4 mmol) in 2 ml of dimethylsulfoxide was then added dropwise. The reaction mixture was stirred for 1 h at room temperature and then poured on water. The phases were separated, the aqueous phase was extracted with dichloromethane, the combined organic layer was washed with water and brine, dried over sodium sulfate and evaporated under reduced pressure.The remainder was purified by chromatography on silica gel, using ethyl acetate/ heptane 1 : 1 as eluent system to deliver 2-[5-(2,4-dichlorophenyl)-1,3-dithian-2-ylidene]-2-imidazol-1-yl-acetonitrile (26, 0.49 g, 1.3 mmol, 92 %) as an inseparable 1 : 1 mixture of the E- and Z-isomer. 1H-NMR (400 MHz, CDCl3): delta= 3.12 (dd, 1H, J = 7.1, 14.1 Hz), 3.18 (dd, 1H, J = 6.8, 14.1 Hz), 3.31 (dd, 1H, J= 6.8, 14.1 Hz), 3.49 (dd, 1H, J = 7.1, 14.1 Hz), 4.10 (q, 1H, J = 7.1 Hz), 7.02 (t,1H, J = 1.3 Hz), 7.17 (s, 1H), 7.29 (dd, 1H, J = 2.2, 8.4 Hz), 7.44 (d, 1H, J = 2.2Hz), 7.48 (d, 1H, J = 8.4 Hz), 7.59 (s, 1H). LC-MS: Rt = 0.97 min; MS: m/z = 368[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 2-(1H-Imidazol-1-yl)acetonitrile, its application will become more common.

Reference:
Article; Gagnepain, Julien; Jeanmart, Stephane; Bonvalot, Damien; Jacob, Olivier; Lamberth, Clemens; Synlett; vol. 30; 1; (2019); p. 59 – 62;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 1632-83-3, The chemical industry reduces the impact on the environment during synthesis 1632-83-3, name is 1-Methylbenzimidazole, I believe this compound will play a more active role in future production and life.

General procedure: 4.3 General procedure for CuO-catalyzed arylation and alkenylation of 1,3-azole (0012) Under argon, 0.5mmol of the bromobenzene or bromoalkene was added to the reaction mixture containing 0.25mmol of the benzoxazole, 0.5mmol K2CO3, 0.025mmol CuO, and 0.075mmol PPh3, followed by the addition of 2mL dry diglyme. The sealed reaction tube was stirred at 160C for 5-24h. After cooling, the reaction mixture was centrifuged to remove solid and separated the organic phase. Then, organic phase was extracted and dried over anhydrous MgSO4, and concentrated under reduced pressure after filtered. The residue was purified by column chromatography on silica gel eluted to afford corresponding product.

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, 1-Methylbenzimidazole, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Zhang, Wu; Tian, Yujie; Zhao, Na; Wang, Yuanyuan; Li, Jia; Wang, Zhenghua; Tetrahedron; vol. 70; 36; (2014); p. 6120 – 6126;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem