Tag: M.W=100-200

Synthetic Route of 60-56-0,Some common heterocyclic compound, 60-56-0, name is 1-Methyl-1H-imidazole-2(3H)-thione, molecular formula is C4H6N2S, 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: A mixture of pyridine (1 mmol) in 3 mL dichloromethane was added dropwise to a magnetically stirred solution of 2-mercapto-1-methylimidazole or 5-mercapto-1-methyltetrazole (1 mmol) and acetylenic esters (1 mmol) in 15 mL dichloromethane. The reaction mixture was then stirred for 2 h at room temperature. The solvent was removed under reduced pressure and the residue was purified by silica gel column chromatography using hexane-ethyl acetate as eluent. The solvent was removed under reduced pressure to afford the product.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1-Methyl-1H-imidazole-2(3H)-thione, its application will become more common.

Reference:
Article; Asgharian-Sheykhi, Fahimeh; Hassanabadi, Alireza; Akhgar, Mohammad Reza; Karbalaei-Harofteh, Mina; Khajehpour, Ehsan; Journal of Chemical Research; vol. 37; 9; (2013); p. 523 – 525;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 6775-40-2,Some common heterocyclic compound, 6775-40-2, name is 5-Phenyl-1H-imidazol-2-amine, molecular formula is C9H9N3, 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: A mixture of the corresponding 2-amino-4-arylimidazole 1(1.0 mmol), aromatic aldehyde 2 (2.0 mmol) and ethyl 2-cyanoacetate 15 (1.0 mmol) in 2 mL of 2-propanol was refluxedduring 20-30 min. After cooling, the yellow solid products 16were filtered off and crystallized from iPrOH. 16a: yellowpowder, 30%, mp 239-240 C; 1H NMR (200 MHz, DMSO-d6)delta 9.32 (s, 1H, CHazomethine), 8.12 (d, J = 6.7 Hz, 2, Ar),7.67-7.45 (m, 5, Ar), 7.27-7.04 (m, 10, C5NH2, Ar), 5.15(s, J = 6.7 Hz, 1H, C7H), 4.05-3.84 (m, 2, 23), 1.01(s, J = 7.0, 3H, 2CH3); 13C NMR (125 MHz, DMSO-d6) delta178.7 (CO), 134.5, 133.3, 130.2, 129.6, 128.7, 128.6, 128.3, 127.8, 127.2, 127.0, 126.4, 125.8, 125.5, 116.7, 93.4, 58.9, 43.4,14.7; MS (m/z) (%): 448 ([M+?], 100; anal. calcd. forC28H24N4O2 (448.19) C, 74.98; H, 5.39; N, 12.49; found: ,75.12; H, 4.89; N, 11.37.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5-Phenyl-1H-imidazol-2-amine, its application will become more common.

Reference:
Article; Lipson, Victoria V.; Pavlovska, Tetiana L.; Svetlichnaya, Nataliya V.; Poryvai, Anna A.; Gorobets, Nikolay Yu.; Van Der Eycken, Erik V.; Konovalova, Irina S.; Shiskina, Svetlana V.; Borisov, Alexander V.; Musatov, Vladimir I.; Mazepa, Alexander V.; Beilstein Journal of Organic Chemistry; vol. 15; (2019); p. 1032 – 1045;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 89830-98-8, name is 5-Cyclopropyl-1H-imidazole, 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 89830-98-8, Product Details of 89830-98-8

General Procedure Synthesis of (1a) To a mixture of 4-cyclopropyl-1H-imidazole (4 g, 37 mmol) and 2-fluoro-5-iodo-4-methyl-benzoic acid (1 eq) in DMSO (200 mL) was added Cu2O (0.05 eq), Cs2CO3 (5 eq) and 8-hydroxyquinioline (0.2 eq) in one portion at 20 C. under N2. The mixture was stirred at 20 C. for 5 min, then heated to 100 C. and stirred for 6 hours. LC-MS showed one main peak with the desired MS. The mixture was concentrated in vacuo. The residue was purified by silica gel column chromatography (SiO2, EtOAc:MeOH:AcOH=1:0:0 to 5:1:0.005) to give 5-(4-cyclopropylimidazol-1-yl)-2-fluoro-4-methyl-benzoic acid (1a). MS mass calculated for [M+1]+ (C14H13FN2O2) requires m/z 261.1, LCMS found m/z 261.1; 1H NMR (400 MHz, DMSO-d6) delta 13.47 (br s, 1H), 8.03-6.96 (m, 4H), 2.20 (s, 3H), 1.94-1.77 (m, 1H), 0.80 (br s, 2H), 0.70 (br s, 2H).

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

Reference:
Patent; Terns, Inc.; XU, Yingzi; HALCOMB, Randall; KIRSCHBERG, Thorsten A.; ROMERO, F. Anthony; (117 pag.)US2019/315767; (2019); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 20034-00-8, name is (5-Nitro-1H-benzo[d]imidazol-2-yl)methanol, 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 20034-00-8, Formula: C8H7N3O3

N-Methyl-2-methanol-5-nitrobenzimidazole 53 was prepared according to using the procedure by Harisha et al. [28]. A solution of 5-nitro-(1H-benzimidazole-2-yl)-methanol 30 (0.86 g, 4.50 mmol), and sodium hydroxide (0.18 g, 4.50 mmol) were stirred in dry acetone (20 mL) for 30 min. Then, iodomethane (0.64 g, 4.50 mmol) was added and the mixture was stirred for 24 h. The reaction mixture was concentrated to a quarter and then poured into ice-cold water. The solid was filtered and washed with 50% HCl to neutralize the excess potassium carbonate. The solid was washed with cold water (100 mL) and aqueous ethanol. The product was purified by column chromatography (9:1 chloroform/ethanol) to give the desired product (FAS50) as an yellow crystals Yield 19%.

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:
Article; Alasmary, Fatmah A.S.; Snelling, Anna M.; Zain, Mohammed E.; Alafeefy, Ahmed M.; Awaad, Amani S.; Karodia, Nazira; Molecules; vol. 20; 8; (2015); p. 15206 – 15223;,
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. 22884-10-2, name is 2-(1H-Imidazol-1-yl)acetic acid, This compound has unique chemical properties. The synthetic route is as follows., SDS of cas: 22884-10-2

Trifluoro acetic acid (2 mL) was added dropwise to a solution of 9b (0.505 g, 1.04 mmol) in dichloromethane (8 mL), and the resultant mixture was stirred at room temperature for 3 h. The solution was concentrated to leave 9c (0.52 g, quantitative) as the crystalline trifluoroacetate salt. This was then dissolved into DMF (10 mL) and ^A iisopropylethylamine (3 mL), and the mixture was stirred at room temperature for 10 min followed by treatment with l-ethyl-3_[3- dimethylamino propyl] carbodiimide hydrochloride (EDC HC1; 0.22 g, 1.14 mmol), N- hydroxybenzotriazole (HOBt; 0.175 g, 1.14 mmol) and 2-(lH-imidazol-l-yl)acetic acid (0.197 g, 1.56 mmol; Tokyo Chemical Industry Co. Ltd.). After stirring under N2 for 16 h, DMF was removed in vacuo and the residue was distributed between dichloromethane and 5% aq sodium carbonate. The organic phase was dried and concentrated to an oil that was purified by flash silica gel chromatography eluting with dichloromethane : methanol : NH4OH (95 : 5 : 0.5). Product fractions were pooled and concentrated to give 10 (0.37 g, 72%) as a yellow oil: NMR (CDCI3) delta 7.49 (s, 1 H), 7.36 (m, 5 H), 7.26 (m, 1 H), 7.09 (s, 1 H), 6.95 (s, 1 H), 6.61 (m, 1H), 5.16 (s, 2 H), 4.75 (s, 2 H), 4.07 (t, J= 5.9 Hz, 2 H), 3.62 (m, 2 H), 3.44 (m, 2 H), 2.42 (t, J= 4.9 Hz, 4 H), 2.39 (t, J= 7.2 Hz, 2 H), 1.81 (m, 2 H), 1.62 (m, 2 H); 13C NMR (CDCI3) delta 164.4, 151.3, 150.8, 138.0, 135.6, 131.0, 129.5, 128.7, 128.2, 127.0, 120.1, 105.9, 105.5, 70.9, 69.1, 57.6, 52.6, 47.9, 45.1, 42.3, 26.7, 22.9; MS (ES+) m/z 494.1 (M+H)+.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 22884-10-2.

Reference:
Patent; THE REGENTS OF THE UNIVERSITY OF MICHIGAN; SHOWALTER, Hollis D.; GARCIA, George A.; XU, Hao; ATWAL, Sumandeep K.; NAWARATHNE, Irosha; KIRCHHOFF, Paul D.; WO2013/86415; (2013); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 614-97-1,Some common heterocyclic compound, 614-97-1, name is 5-Methyl-1H-benzo[d]imidazole, molecular formula is C8H8N2, 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 B – Synthesis of Compounds DD3 and DD4; To a solution of compound DD2 (24.5 mmol) in CH3CN (65 mL) was added di- tertbutyl dicarbonate (5.89 g, 27.0 mmol), triethylamine (3.76 mL, 27.0 mmol) and 4- dimethylamino pyridine (300 mg, 2.45 mmol) and the resulting reaction was heated to 800C and allowed to stir at this temperature for 1.5 hours. The reaction mixture was cooled to room temperature, concentrated in vacuo, and the residue obtained was purified using flash column chromatography (silica gel, EtOAc/Hexanes 5-20%) to provide a mixture of isomeric compounds DD3 and DD4 (5.38 g, 94.3% yield over steps A and B).

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-benzo[d]imidazole, its application will become more common.

Reference:
Patent; SCHERING CORPORATION; WO2008/82488; (2008); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 37052-78-1,Some common heterocyclic compound, 37052-78-1, name is 5-Methoxy-1H-benzo[d]imidazole-2-thiol, molecular formula is C8H8N2OS, 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.

[0176] 6.48 g (33.2 mmol) of 4-bromobutanoate ethyl ester were added to 10 ml of an ethanol solution containing 5.0 g (27.7 mmol) of 5-methoxybenzimidazole-2-thiol followed by stirring for 1 hour at 80 C. and adding 90 ml of ethyl acetate. The reaction solution was returned to room temperature and the formed crystals were filtered out followed by drying to obtain 9.34 g of the target compound (yield: 90%). [0177] 1H-NMR (270 MHz, CDCl3) (ppm): 7.65 (d, 1H, J=8.91 Hz), 7.24 (s, 1H), 7.00 (dd, 1H, J=2.43, 8.91 Hz), 4.21 (q, 2H, J=7.29 Hz), 3.83 (s, 3H), 3.74 (m, 2H), 2.61 (m, 2H), 2.10 (m, 2H), 1.30 (t, 3H, J=7.29 Hz)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5-Methoxy-1H-benzo[d]imidazole-2-thiol, its application will become more common.

Reference:
Patent; Tsuchiya, Naoki; Matsumoto, Yoshiyuki; Saitou, Hiroshi; Mizuno, Tsuyoshi; US2004/10004; (2004); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 2302-25-2, 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. 2302-25-2, name is 4-Bromo-1H-imidazole belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

To a solution of 4-bromo-1H-imidazole 1a (2 g, 13.70 mmol) in DMF (30 mL) was added 2,2-dimethyloxiraneIf (20 mL) and Cs2CO3 (8 g, 24.62 mmol). The mixture was stirred at 90 C overnight. Then the mixture was evaporatedto dryness. The residue was dissolved in DCM (30 mL), washed with water (10 mL*2) and brine (10 mL), dried overNa2SO4, filtered and concentrated to give the target compound 1-(4-bromo-1H-imidazol-1-yl)-2-methylpropan-2-ol 1b(2.7 g, pale yellow solid), yield: 90.6%.1H NMR(400 MHz, CDCl3) delta 7.33 (s, 1H), 6.94 (s, 1 H), 3.82 (s, 2H), 1.22 (s, 6H)

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

Reference:
Patent; Medshine Discovery Inc.; Quingdao Huanghai Pharmaceutical Co., Ltd.; WU, Chengde; ZHANG, Zhiliu; YU, Tao; (125 pag.)EP3042907; (2016); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 33543-78-1,Some common heterocyclic compound, 33543-78-1, name is Ethyl 1H-imidazole-2-carboxylate, molecular formula is C6H8N2O2, 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.

5-Phenylcarbamoyl-2-(2-ethoxycarbonylimidazolyl)-1-indanone can be prepared in the following way: the preparation is carried out as in Example 19 for 4-benzylcarbamoyl-2-(2-ethoxycarbonylimidazolyl)-1-indanone but from 3.65 g of 5-phenylcarbamoyl-2-bromo-1-indanone, 73 ml of toluene and 3.1 g of 2-ethoxycarbonylimidazole. The crude product is purified by chromatography on a silica column, elution being carried out first with a dichloromethane/methanol (99.5/0.5 by volume) mixture and then with a dichloromethane/methanol (98/2 by volume) mixture. 0.9 g of 5-phenylcarbamoyl-2-(2-ethoxycarbonylimidazolyl)-1-indanone is obtained in the form of a brown solid melting at 122¡ã C. 5-Phenylcarbamoyl-2-bromo-1-indanone can be prepared in the following way:

The synthetic route of 33543-78-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Rhone-Poulenc Rorer S.A.; US5902803; (1999); 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. 7152-24-1, name is 2-(Methylthio)benzimidazole, A new synthetic method of this compound is introduced below., name: 2-(Methylthio)benzimidazole

(202a) A solution of methyl (4-bromomethyl)benzoate (1.0 g, 4.4 mmol) in dimethylsulfoxide (DMSO) (43 mL) was treated with 2-(methylthio)benzimidazole (0.7 g, 1 eq) and Cs2CO3 (2.1 g, 1.5 eq) and stirred for 2 hr at rt. The mixture was then partitioned between water and ethyl acetate (40 mL each) and the aqueous layer was further extracted with ethyl acetate (40 mL) and the combined organic layers washed with brine (40 mL), dried (Na2SO4), filtered and concentrated. Flash chromatography (SiO2, MeOH/dichloromethane, 1:40 v/v) provided the desired ester (0.8 g, 62%) as a white sold. MS found: (M+H)+=313.

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; Sheppeck, James E.; Duan, Jingwu; Xue, Chu-Biao; Wasserman, Zelda; US2003/130273; (2003); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem