Tag: M.W=100-200

Some common heterocyclic compound, 172499-76-2, name is Ethyl 3-(1H-imidazol-2-yl)propanoate, molecular formula is C8H12N2O2, 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. Application In Synthesis of Ethyl 3-(1H-imidazol-2-yl)propanoate

(ii) Production of ethyl 3-[1-[4-[4-[[2-[(E)-2-[4-(trifluoromethyl)phenyl]ethenyl]-1,3-oxazol-4-yl]methoxy]phenyl]butyl]-1H-imidazol-2-yl]propionate A suspension of 4-[[4-(4-iodobutyl)phenoxy]methyl]-2-[(E)-2-[4-(trifluoromethyl)phenyl]ethenyl]-1,3-oxazole (6.00 g), ethyl 3-(1H-imidazol-2-yl)propionate (3.83 g) and potassium carbonate (1.58 g) in DMF (100 ml) was stirred at 70C for 23 hr. The reaction mixture was combined with water and extracted with ethyl acetate. The extract was successively washed with water and saturated brine and dried over magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (eluent; ethyl acetate) and washed with diethyl ether-hexane to give the titled compound (3.69 g) as a colorless amorphous form.1H-NMR (CDCl3) delta: 1.25 (3H, t, J = 7.2 Hz), 1.59-1.79 (4H, m), 2.59 (2H, t, J = 7.0 Hz), 2.88-2.91 (4H, m), 3.87 (2H, t, J = 7.0 Hz), 4.14 (2H, q, J = 7.2 Hz), 5.02 (2H, d, J = 0.8 Hz), 6.79 (1H, d, J = 1.4 Hz), 6.90-7.06 (6H, m), 7.10 (1H, s), 7.52-7.69 (5H, m). IR (KBr): 1732, 1510, 1325, 1167, 1123, 1067 cm-1.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 172499-76-2, its application will become more common.

Reference:
Patent; Takeda Chemical Industries, Ltd.; EP1439178; (2004); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

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. COA of Formula: C5H6N2O

A mixture of i-methyMH-imidazole-4-carbaldehyde (0.50 g), N- bromosuccinimide (0.89 g) and chloroform (7.0 ml_) was heated at reflux for 2 hours. The mixture was cooled to O0C, diluted with saturated aqueous sodium carbonate solution (10 ml_) and extracted with dichloromethane. The combined organic extract was dried over magnesium sulfate and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel, eluting with a mixture of ethyl acetate and dichloromethane (0:1 to 7:10 by volume) to afford the title compound as a white solid (0.37 g).1H NMR (CDCl3): delta 3.70 (s, 3H), 7.66 (s, 1 H), 9.89 (s, 1 H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 17289-26-8, its application will become more common.

Reference:
Patent; ARGENTA DISCOVERY LIMITED; WO2009/77728; (2009); A1;,
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. 38993-84-9, name is (1-Methyl-1H-imidazol-5-yl)methanol, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 38993-84-9

Add thionyl chloride (4.00 ml, 53.8 mmol) to a solution of (3-methyl-3H- imidazol-4-yl)-methanol (4.0 g, 35.7 mmol) in dichloroethane (30 mL) and stir at room temperature for 18 h. Concentrate the reaction mixture and add ether to the residue. Sonicate for 5 min, filter, and dry to give the title compound (5.8 g, 98percent). MS (ES+) 131 (M+l)+. 1H NMR (400 MHz, DMSO-d6): delta 14.99 (s, 1H), 9.18 (s, 1H), 7.75 (s, 1H), 5.00 (s, 2H), 3.85 (s, 3H).

According to the analysis of related databases, 38993-84-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ELI LILLY AND COMPANY; WO2006/66174; (2006); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 615-16-7, 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. 615-16-7 name is 2-Hydroxybenzimidazole, 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: 4-Bromo-2-(substituted) benzonitrile 5a or 5b (5 mmol) was added to a mixture of 1H-benzo[d]imidazol-2(3H)-one (6) (10 mmol) and Cs2CO3 (10 mmol) in DMF (25.0 ml). After 12 h, 50 ml of ice water was added dropwise. The resulting suspension was filtered, and the filter cake was dried in a vacuum oven. The solid was purified by flash chromatography (50 % ethyl acetate in hexane) to afford 4-(2-oxo-2,3-dihydro-1H-benzo[d]imidazol-1-yl)-2-(substituted) benzonitrile (7a or 7b). 2-(Trifluoromethyl)-4-(1,2-dihydro-2-oxobenzo[d]imidazol-3-yl) benzonitrile (7a) Yield 62 %; White Solid; mp 232-233 C; IR (KBr) nu max: 3189, 3149 (N-Hstretch), 3072 (C-Harom), 2957, 2895, 2820 (C-Halk), 2230 (C:N), 1720 (C=O), 1611 (N-Hbend), 1575, 1507, 1481, 1439 (C=Carom), 1385, 1319, 1240, 1185, 1127, 1053 (C-Hbend), 1272, 558 (C-CF3) cm-1; 1H NMR (400 MHz, CDCl3, ppm): delta 9.372 (s, 1H, NH), 8.14 (s, 1H, H-2), 8.03 (d, 2H, H-5,H-6), 7.2 (m, 4H, phenyl); 13C NMR (100 MHz, CDCl3, ppm): delta 152.9 (C=O), 139.2 (C4), 135.6 (C6), 133.8, 133.1 (q, J = 65 Hz, C2), 128.5 (C0 1), 127.6 (d, J = 34 Hz, C5), 123.3 (C0 6), 122.8 (C0 3), 122.5 (q, CF3), 121.6 (C), 120.4 (C0 5), 114.8 (CN), 110.0 (C0 2), 108.7 (C0 4), 106.6 (C1); HRMS (ESI): m/z calculated for C15H8F3N3O [M?H]?: 304.06922; Found: 304.069.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-Hydroxybenzimidazole, and friends who are interested can also refer to it.

Reference:
Article; Elancheran; Saravanan; Choudhury, Bhaswati; Divakar; Kabilan; Ramanathan; Das, Babulal; Devi; Kotoky, Jibon; Medicinal Chemistry Research; vol. 25; 4; (2016); p. 539 – 552;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 32673-41-9,Some common heterocyclic compound, 32673-41-9, name is 4-Imidazolemethanol hydrochloride, molecular formula is C4H7ClN2O, 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.

Step 1 Preparation of 1-triphenylmethyl-4-(hydroxymethyl)imidazole To a solution of 4-(hydroxymethyl)imidazole hydrochloride (35 g) in 250 mL of dry DMF at room temperature was added triethylamine (90.6 mL). A white solid precipitated from the solution. Chlorotriphenylmethane (76.1 g) 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 title compound as a white solid which was sufficiently pure for use in the next step.

The synthetic route of 32673-41-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Merck & Co., Inc.; US6015817; (2000); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 45676-04-8, 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. 45676-04-8, name is 1-tert-Butylimidazole belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

The procedure given for the synthesis of [DPCP-(ImidMe)2]Cl2 was followed. Yield: 92%. mp: 170-173 C. 1H NMR (400 MHz, CDCl3): delta 12.00 (s, 2H, imidazole-NCHN), 8.47 (s, 2H, imidazole-NCHCHN), 8.10 (s, 2H, imidazole-NCHCHN), 7.73 (m, 6H, Ph-H), 7.62 (m, 4H, Ph-H), 1.90 [s, 18H, C(CH3)3] ppm. 13C NMR (100 MHz, CDCl3): delta 159.86, 137.69, 134.90, 131.27, 129.76, 129.03, 128.22, 127.61, 122.01, 119.29, 62.83, 30.35 ppm. 31P (161 MHz, CDCl3): delta 41.89 ppm (s).

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

Reference:
Article; Senkuttuvan; Ramakrishna; Bakthavachalam; Reddy, N. Dastagiri; Journal of Organometallic Chemistry; vol. 723; (2013); p. 72 – 78;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 3034-42-2, name is 1-Methyl-5-nitroimidazole, 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 3034-42-2, Recommanded Product: 3034-42-2

General procedure: To a solution of 1-methylimidazole derivatives (1 mmol) in adequate volume of acetonitrile, was added 1.5 mmol of 2-bromoacetophenone (1.8 mmol of ethylbromoactate). The reaction mixture was refluxed. When the reaction was(TLC), the solvent volume was reduced and the crude product was then filtered off and washed with cold acetonitrile.

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-Methyl-5-nitroimidazole, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Bahnous, Mebarek; Bouraiou, Abdelmalek; Chelghoum, Meryem; Bouacida, Sofiane; Roisnel, Thierry; Smati, Farida; Bentchouala, Chafia; Gros, Philippe C.; Belfaitah, Ali; Bioorganic and Medicinal Chemistry Letters; vol. 23; 5; (2013); p. 1274 – 1278;,
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. 1615-14-1, name is 2-(1H-Imidazol-1-yl)ethanol, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of 2-(1H-Imidazol-1-yl)ethanol

The mixture containing 1.0 g (8.9 mmol) of 1-(2-hydroxyethyl)imidazole and 2.99 g (9.8 mmol) of 1-hexadecylbromide dissolved in 10 mL of acetonitrile was boiled with reflux condenser for 24 h. The precipitate formed during cooling was filtered, purified by recrystallization from ethyl acetate and dried under vacuum. Yield: 2.25 g (58%). Mp=52-54 C.IR-spectrum (KBr), cm-1: 3532, 3330, 3134, 3069, 2917, 2850, 1564,1472, 1379, 1165,1071, 873, 792, 720. 1H NMR spectrum, 400 MHz(CDCl3), delta, ppm, J/Hz: 0.88 t (3H, J=6.8), 1.25-1.33m (26 H), 1.91m(2 H), 3.98 t (2H, J=4.91), 4.26 t (2H, J=7.64), 4.53 t (2H, J=7.90),7.31 d (1 H), 7.63 d (1 H), 9.73 s (1 H). ESI MS, m/z: 337.6[M-Br]+.Calculated, %: C21H41N2OBr: C 60.42; H 9.89; N 6.71; Br 19.14; found,%: C 60.23; H 10.12; N 6.45; Br 19.07.

According to the analysis of related databases, 1615-14-1, the application of this compound in the production field has become more and more popular.

Reference:
Article; Kuznetsova, Darya A.; Gabdrakhmanov, Dinar R.; Lukashenko, Svetlana S.; Voloshina, Alexandra D.; Sapunova, Anastasiia S.; Kashapov, Ruslan R.; Zakharova, Lucia Ya.; Chemistry and Physics of Lipids; vol. 223; (2019);,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 39070-14-9, A common heterocyclic compound, 39070-14-9, name is (1-Methyl-2-nitro-1H-imidazol-5-yl)methanol, molecular formula is C5H7N3O3, 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 61: 1-Methyl-2-nitro-5-imidazolaldehyde To a solution of 0.15 g. of 1-methyl-2-nitro-5-hydroxymethylimidazole in 20 ml. of benzene, 0.33 g. of MnO2 is added and the reaction mixture is heated on the steambath for 2 hours. After filtration and evaporation to dryness under vacuum, the crude product is crystallized from ethyl acetate and 0.060 g. (40.5%) of 1-methyl-2-nitro-5-imidazolaldehyde is obtained.

The synthetic route of 39070-14-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Gruppo Lepetit S.p.A.; US3954789; (1976); A;,
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. 15965-54-5, name is 2-Chloro-5-methoxy-1H-benzo[d]imidazole, A new synthetic method of this compound is introduced below., Quality Control of 2-Chloro-5-methoxy-1H-benzo[d]imidazole

EXAMPLE 100 0.55 Gram of 2-chloro-5-methoxybenzimidazole, 0.2 g of thiourea and 10 ml of ethanol were mixed together and refluxed for 2 hours. Then, 5 ml of an aqueous solution containing 0.5 g of 3-methyl-8-bromo-5,6,7,8-tetrahydroquinoline and 0.3 g of sodium hydroxide was added thereto, and the resulting mixture was refluxed for 5 hours. After the reaction was completed, ethanol was removed by evaporation, to the residue thus obtained was added water, then extracted with chloroform, the chloroform extract was dried with anhydrous magnesium sulfate, and chloroform was removed by evaporation. The residue thus obtained was purified by means of a silica gel column chromatography (eluent: dichloromethane/methanol=100/1) to yield 0.5 g of 8-(5-methoxy-2-benzimidazolyl)thio-3-methyl-5,6,7,8-tetrahydroquinoline in the form of colorless caramel-like substance. NMR (CDCl3) delta: 1.60-2.00 (m, 2H), 2.00-2.40 (m, 2H), 2.27 (s, 3H), 2.72 (t, 2H), 3.78 (s, 3H), 4.78 (t, 1H), 6.77 (dd, 1H), 7.00 (d, 1H), 7.22 (d, 1H), 7.40 (d, 1H), 8.23 (d, 1H).

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; Otsuka Pharmaceutical Co., Ltd.; US4738970; (1988); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem