Month: June 2021

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. 3012-80-4, name is 1-Methyl-1H-benzo[d]imidazole-2-carbaldehyde, This compound has unique chemical properties. The synthetic route is as follows., category: imidazoles-derivatives

General procedure: Benzimidazole 1 (1mmol) was added to the mixture of AlCl3 or AlBr3 (5.0 mmol) in benzene (3 mL). The reactionmixture was stirred at room temperature for the time as indicated in Table 1. The mixture wasquenched with ice water (50 mL), extracted and worked-up as described above.

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 3012-80-4.

Reference:
Article; Ryabukhin, Dmitry S.; Turdakov, Alexey N.; Soldatova, Natalia S.; Kompanets, Mikhail O.; Ivanov, Alexander Yu.; Boyarskaya, Irina A.; Vasilyev, Aleksander V.; Beilstein Journal of Organic Chemistry; vol. 15; (2019); p. 1962 – 1973;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 128293-62-9, name is Ethyl 4-amino-1-methyl-1H-imidazole-2-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 128293-62-9, HPLC of Formula: C7H11N3O2

The compound 7 was dissolved in methanol (94.4 ml), mixed with 10 % Pd/C (1.18 g) and stirred for four hours under hydrogen atmosphere. 10% Pd/C was removed from the reaction system with cerite filtration, so that the solvent was distilled out under a reduced pressure. Dimethylformamide (10 ml) was added to the residue and distilled out again under a reduced pressure. The residue was dissolved in dimethylformamide (10 mL) again, and mixed with the compound 8 (5. 9 g, 23.6mmol) (Baird, E. E. ; Dervan, P. B. J. Org. Chem. 1996, 118, 6141-6146), EDC (9.05 g, 47.2 mmol) and dimethylaminopyridine (288 mg, 2. 36 mmol), and stirred for 12 hours at a room temperature. Re-precipitation treatment with chloroform and ethyl acetate gave the compound 9 as white powder (5.9 g, 63%). 1HNMR(DMSO-d6) delta 1.28-1.30 (3H, t, J = 7.1 Hz), 3.85(3H, s), 3.93(3H, s), 3.98(3H, s), 4.25-4.29 (2H, dd, J = 7.1 Hz), 7.03(1H, d, J = 0.7 Hz), 7.22(1H, d, J = 2.0 Hz), 7.38(1H, s), 7.38(1H, s), 7.66(1H, s), 10.35(1H, s), 10.74(1H, s) ; 13CNMR(DMSO-d6) delta 14.3, 35.3, 35.7, 36.5, 60.8, 106.4, 115.6, 119.8, 121.6, 122.2, 126.5, 127.2, 131.0, 138.0, 139.0, 156.3, 158.7, 158.9: Anal. Calcd. for C18H12N4O3·H2O: C, 53.22; H, 4.89; N, 22.57. Found: C, 50.88; H,4.88; N,23.13.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Ethyl 4-amino-1-methyl-1H-imidazole-2-carboxylate, and friends who are interested can also refer to it.

Reference:
Patent; Japan Science and Technology Agency; EP1719777; (2006); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 2034-22-2,Some common heterocyclic compound, 2034-22-2, name is 2,4,5-Tribromoimidazole, molecular formula is C3HBr3N2, 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.

STAGE 1: 1-((6-chloro-1,3-benzodioxol-5-yl)-methyl)-2,4,5-tribromo-1H-imidazole 25 g of 2,4,5-tribromoimidazole is introduced into 500 ml of dimethylformamide and 4.3 g of sodium hydride is added. Agitation is maintained for 10 minutes at ambient temperature. Next 18.4 g of 6-chloro piperonyl chloride, then 25 g of sodium iodide are added to the reaction medium and agitation is continued for 15 minutes at ambient temperature. The reaction medium is finally poured into 3 litres of water, separated, washed abundantly with water, then successively with 250 ml of ethanol, 250 ml of isopropanol, then finally with 250 ml of isopropyl ether. After drying, 31.5 g of expected product (cream solid) is collected M.p.=225 C. IR CHCl3 (cm-1) Absence of =C–NH

The synthetic route of 2034-22-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Hoechst Marion Roussel; US6143774; (2000); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 570-22-9,Some common heterocyclic compound, 570-22-9, name is 1H-Imidazole-4,5-dicarboxylic acid, molecular formula is C5H4N2O4, 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.

Scheme A, step a [4S-[4alpha, 7alpha(R*), 12bbeta]]-7-[(5-(4-methoxybenzylthio)-5-oxo-1-(carbo-t-butyloxy)-4,5-dihydrocyclopentimidazole)methylamino]-3,4,6,7,8,12b-hexahydro-6-oxo-1H-[1,4]-oxazino[3,4-a][2]benzazepine Dissolve 4,5-imidazoledicarboxylic acid (31.2 g, 0.2 mol) in ethanol (500 mL) and treat with concentrated sulfuric acid (0.5 mL). Heat to 60 C. for 16 hours, cool and reduce the solvent by 50% in vacuo. Dilute with ethyl ether (500 mL), wash with saturated sodium hydrogen carbonate, then brine. Dry (MgSO4) and evaporate the solvent in vacuo to give 4,5-(dicarboethoxy)imidazole.

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

Reference:
Patent; Merrell Dow Pharmaceuticals, Inc.; US5420271; (1995); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 123470-47-3, 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. 123470-47-3, name is 5,6-Difluoro-1H-benzo[d]imidazole-2(3H)-thione, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: An oven-dried Schlenk tube equipped with a Teflon valve was charged with a magnetic stir bar, CuI (0.075 mmol), 1,10-phenanthroline (0.15 mmol), 1,8-diiodonaphthalene 1a (0.5 mmol), 1H-benzo[d]imidazole-2-thiols or 2-thiouracils b (0.5 mmol) and base (1.0 mmol). The tube was placed under vacuum for twenty minutes and backfilled with N2, then DMF (2.0 mL) was added via syringe. The reaction mixture was stirred at 100 oC for 24 h. The reaction was monitored by TLC. When b consumed completely, the reaction was stopped and cooled to room temperature, EtOAc (40 mL) was added and the mixture was washed with brine (20 mL × 3). The organic phase was dried over Na2SO4 and concentrated. The residue was purified by column chromatography on silica gel using petrol/EtOAc (3:1, v:v) as eluent to give c.

The chemical industry reduces the impact on the environment during synthesis 5,6-Difluoro-1H-benzo[d]imidazole-2(3H)-thione. I believe this compound will play a more active role in future production and life.

Reference:
Article; Cui, Jichun; Zhang, Tongxin; Wang, Jianhua; Liu, Dezhi; Wang, Jiaqian; Liu, Jie; Shen, Guodong; Synthetic Communications; vol. 49; 8; (2019); p. 1076 – 1082;,
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. 10111-08-7, name is Imidazole-2-carboxaldehyde, A new synthetic method of this compound is introduced below., Recommanded Product: 10111-08-7

Compound 26-2 (0449) To a solution of 2-imidazolecarboxyaldehyde (26-1) (1.92 g, 20 mmol, 1.0 eq) was suspended in methanol (30 mL), NaBH4 (1.52 g, 40 mmol, 2.0 eq) was added portion-wise. The reaction mixture was stirred at room temperature for 1 h under N2. It was quenched with 5 mL of brine. The solvent was removed and the solid was purified with silica gel column chromatography (DCM:MeOH=20:1) to afford a white solid. (1.0 g, Yield: 51%).

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; Nivalis Therapeutics, Inc.; Wasley, Jan; Rosenthal, Gary J.; Sun, Xicheng; Strong, Sarah; Qiu, Jian; US9138427; (2015); B2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 641571-11-1, 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. 641571-11-1 name is 3-(4-Methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)aniline, 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.

Example 2; Recrystallization of 3-(trifluoromethyl)-5-(4-methyl-1H-imidazole-1-yl)-benzeneamine of formula I from IPA/waterA 50 mL flask was charged with 1 g of the compound of Formula I crude (purity of 82.5%) and 3.5 mL of IPA. The mixture was heated to 45 C. under stirring until the entire solid dissolved. At 45 C., 6 mL of water was added drop-wise. The mixture was stirred for 10 min and cooled slowly to 010 C. The mixture was stirred at 010 C. for 10 min and filtered to obtain the recrystallized compound of Formula I having a purity of 98%.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3-(4-Methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)aniline, and friends who are interested can also refer to it.

Reference:
Patent; TEVA PHARMACEUTICAL INDUSTRIES LTD.; US2010/16590; (2010); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 29043-48-9, These common heterocyclic compound, 29043-48-9, name is 2-Methyl-1H-benzoimidazol-5-ylamine, 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.

The coupling reaction of 3-chloro-2-methylbenzenesulphonyl chloride (2 eq. ) with 2- methylbenzimidazoel (1 eq. ) under the condition described above yielded a mixture of 3- CHLORO-N- [1- (3-CHLORO-2-METHYLBENZENESULPHONYL)-2-METHYL-1 H-BENZOIMIDAZOL-5-YL]-2- methyl-benzenesulphonamide and 3-chloro-N-[1-(3-chloro-2-methylbenzenesulphonyl)- 2-METHYL-1 H-BENZOIMIDAZOL-6-YL]-2-METHYL-BENZENESULPHONAMIDE in 1: 1 ratio as judged by HNMR.’H NMR (270 MHz, DMSO): 5 10.7 (2H, s, 2 x NH), 7.86-7. 96 (3H, m, ArH), 7.65-7. 78 (5H, m, ArH), 7.52-7. 58 (5H, m, ArH), 7.25-7. 40 (3H, m, ArH), 7.07 (2H, t, J = 8.2 Hz, ArH), 2.61 (3H, s, CH3), 2.58 (3H, s, CH3), 2.54 (6H, s, 2 x CH3), 2.39 (3H, S, CH3), 2.33 (3H, s, CH3). The mixture (200 mg) was dissolved in THF (15 mL), N- hydroxybenzotriazole (200 mg) was added. After stirred at rt for 48h, the mixture was partitioned between ethyl acetate and 5% sodium bicarbonate. The organic phase was washed with brine, dried over sodium sulphate and concentrate in vacuo to give a yellow residue, which was purified with flash chromatography (methanol/DCM gradient elution). Off white amorphous powder was obtained. TLC single spot at Rf 0.38 (10% methanol/DCM) ; HPLC purity 99% (tR 2.0 min in 10% WATER-METHANOL) ;’H NMR (270 MHz, DMSO): 5 12.1 (1H, s, NH), 10.3 (1H, s, NH), 7.78 (1H, d, J = 7.9 Hz, ArH), 7.68 (1H, d, J= 7.9 Hz, ArH), 7.29-7. 35 (2H, m, ArH), 7.12 (1H, s, ArH), 6.83 (1H, dd, J= 8.4, 1.8 Hz, ArH), 2.63 (3H, s, CH3), 2.41 (3H, s, CH3) ; APCI-MS 334 (M-H+) ; FAB-HRMS calcd for C1SH1SCIN302S (MH+) 336.0573, found 336.0583.

Statistics shows that 2-Methyl-1H-benzoimidazol-5-ylamine is playing an increasingly important role. we look forward to future research findings about 29043-48-9.

Reference:
Patent; STERIX LIMITED; WO2004/37251; (2004); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 17325-26-7, 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 17325-26-7 as follows.

Into an 18 mL vial was added Methyl 4-imidazolecarboxylate (113 mg, 0.90 mmol), DMF (3 mL), and NaH (43 mg, 1.08 mmol). After 20 minutes at room temperature Int-20 (295 mg, 0.90 mmol) was added. The reaction was stirred for 2 hours at room temperature and then water was added. The product was extracted with EtOAc and the organics were concentrated. The residue was purified by flash column chromatography eluting with 6%-10% Acetone/DCM to separate the regioisomers. The 4-substituted ester (Int-53, 67 mg, 20%) and the 2-substituted ester (Int-54, 79 mg, 23%) were obtained as colorless oils.

According to the analysis of related databases, 17325-26-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; DECODE GENETICS EHF; US2009/136473; (2009); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 75370-65-9, 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. 75370-65-9, name is 4-Amino-1H-benzo[d]imidazol-2(3H)-one belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

Example 3 1-(2-chloro-4-(trifluoromethyl)benzyl)-3-(2,3-dihydro-2-oxo-1H-benzo[d]imidazol-4-yl)urea (scheme 1) Commercially available 2-chloro-4-trifluoromethylbenzylamine (700 mg, 3.3 mmol) was dissolved in 20ml of AcOEt and at 0C triphosgene (989mg, 3.3mmol) was added to the solution. The mixture was warmed at 80C for 4 hours then evaporated and the residue was dissolved in 5 ml of DMF. The solution of the isocyanate was added dropwise to a solution in DMF (5 ml) of compound 1a (319 mg, 2.14 mmol) and the mixture was warmed at 80C for 8 hours. (TLC AcOEt 9.5 / MeOH 0.5). The solvent was evaporated and the crude was dissolved in AcOEt (30ml) and washed with water (1 X 20 ml) and brine. The organic phase was dried over sodium sulfate and concentrated under vacuum. The purification of the crude residue by chromatographic column gave 140 mg of a white solid. Yield = 18% 1HNMR (DMSO, 400 MHz) delta 4.44 (2H, d, J = 5.6 Hz), 6.64 (1H, d, J = 7.2 Hz), 6.84 (1H, t, J = 8.4 Hz), 6.89 (1H, t), 6.96 (1H, d, J = 8 Hz), 7.64 (1H, d, J = 8.4 Hz), 7.74 (1H, d), 7.86 (1H, s), 8.43 (1H, bs), 9.99 (1H, bs), 10.61 (1H, bs); [M+1] 385.0 (C16H12C12C1F3N4O2 requires 384.74).

The synthetic route of 4-Amino-1H-benzo[d]imidazol-2(3H)-one has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Pharmeste S.r.l.; EP2377850; (2011); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem