Tag: M.W=100-200

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. 32673-41-9, name is 4-Imidazolemethanol hydrochloride, A new synthetic method of this compound is introduced below., Safety of 4-Imidazolemethanol hydrochloride

0.2 Mol 4-hydroxymethyl imidazole hydrochloride is added to 270 ml thionyl bromide, which has been cooled to 0C. The yellow-coloured solution is allowed to return to room temperature. Excess thionyl bromide is distillated for 45 minutes under reduced pressure. The remainder solidifies upon cooling. The yield of 4-bromomethyl imidazole hydrobromide salt is about 50%.

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; Stichting Biomaterials, Science Center, VU, “BSC-VU”; EP364016; (1990); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

71759-89-2, The chemical industry reduces the impact on the environment during synthesis 71759-89-2, name is 5-Iodo-1H-imidazole, I believe this compound will play a more active role in future production and life.

4-Iodoimidazole (0101-1) (10.0 g, 51.6 mmol, 1.0 eq.)Dissolved in 150 ml of tetrahydrofuran,Triphenylmethyl chloride (17.2 g, 61.7 mmol, 1.2 equivalents) andTriethylamine (14.5 ml, 10.4 mmol, 2.0 eq),Heat to 80C and react overnight.Cooled to room temperature, concentrated under reduced pressure, added ethyl acetate, washed with water, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. Methanol and a small amount of dichloromethane were added and stirred for half an hour. The solid was collected by suction, washed twice with methanol, and vacuum dried. ,4-Iodo-1-trityl-1H-imidazole (16 g, yield: 71%) was obtained as a white solid.

The chemical industry reduces the impact on the environment during synthesis 5-Iodo-1H-imidazole. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Guangzhou Bi Beite Pharmaceutical Co., Ltd.; Cai Xiong; Qian Changgeng; Weng Yunwo; Qing Yuanhui; Liu Bin; Lin Mingsheng; Wang Yanyan; (126 pag.)CN107383024; (2017); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 51605-32-4, A common heterocyclic compound, 51605-32-4, name is Ethyl 5-methyl-1H-imidazole-4-carboxylate, molecular formula is C7H10N2O2, 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.

Ethyl 4-methyl-1 H-imidazole-5-carboxylate (463 mg, 3.00 mmol, 1 eq) was combined with iodomethane (0.19 mL, 3.00 mmol, 1 eq) and potassium carbonate (828 mg, 6.00 mmol, 2 eq) in acetonitrile and stirred overnight at reflux. The reaction mixture was cooled to ambient temperature, inorganics filtered off, and the filtrate concentrated to dryness. The residue was purified on an 80 g silica gel cartridge eluted with 100percent EtOAc to 10percent CH3OH/DCM to give the two regioisomeric products. The first eluting isomer was identified as the title compound (185 mg, 1.95 mmol, 35percent) by comparative NOESY and HMBC NMR. 1 H NMR (400 MHz, DMSO- d6) delta ppm 7.74 (s, 1 H), 4.25 (q, J=7.14 Hz, 2 H), 3.76 (s, 3 H), 2.34 (s, 3 H), 1.30 (t, J=7.10 Hz, 3 H). LC-MS (ES+) m/z 169.08 [M+H]

The synthetic route of 51605-32-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SMITHKLINE BEECHAM CORPORATION; WO2008/157273; (2008); A1;,
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. 16681-59-7, name is 2-Bromo-1-methyl-1H-imidazole, A new synthetic method of this compound is introduced below., SDS of cas: 16681-59-7

Step 2 To a 500 mL round flask was added N-methyl-2-bromoimidazole (6.50 g, 40 mmol),2,4-diflurophenylboronic acid (7.89g, 50 mmol), palladium(II) acetate (0.28 g, 1.25 mmol), triphenylphosphine (1.31 g, 5 mmol), sodium carbonate (14.31 g, 135 mmol), and 200 mL of DME and 100 mL of water. The reaction was heated to reflux and stirred under a nitrogen atmosphere for 12 hours. The mixture was extracted with ethyl acetate and further purified by a silica gel column. Distillation of the product at 150 C. gave N-methyl-2-(2,4-difluorophenyl)imidazole as a colorless oil (6.60 g, 85% yield), characterized by 1H-NMR and MS.

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; Lin, Chun; Ma, Bin; Knowles, David B.; Brooks, Jason; Kwong, Raymond; US2006/8670; (2006); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

705-09-9, Adding a certain compound to certain chemical reactions, such as: 705-09-9, name is 2-(Difluoromethyl)-1H-benzo[d]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 705-09-9.

Step 2: NaH (60%, l . lg, 45.8mmol, 1.5eq) was added protion-wise to a solution of compound Id (3.4g, 20.1mmol, l .leq) in DMF(50mL) at 0C and the mixture was stirred at r.t for 45min. Compound 5a (5.0g, 18.3mmol, leq) was added to the mixture. The mixture was stirred at r.t over weekend. Water was added and the mixture was extracted with ethyl acetate, the organic layer was washed with water for 3 times, dried, concentrated and purified by column chromatography to give 5b (3.4g, yield: 45.8%) as a white solid.’H NMR(CDC13, 300MHZ, ppm): delta 10.23(s, 1H), 7.72(d, 1H), 7.54(d, 1H)ES-MS m/z: 321(M+H+).

According to the analysis of related databases, 705-09-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; TYROGENEX, INC.; LIANG, Congxin; WO2011/41399; (2011); A2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 38993-84-9, name is (1-Methyl-1H-imidazol-5-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 38993-84-9, Formula: C5H8N2O

A mixture of 4-chloro-3,5-diphenyl-1H-pyrazolo[3,4-c]pyridazine (100 mg, 0.33 mmol), 1-methyl-1H-imidazol-5-yl)methanol (73 mg, 0.65 mmol), diethyl azodicarboxylate (114 mg, 0.65 mmol) and triphenyl phosphine (171 mg, 0.65 mmol) in 1,4-dioxane (2 mL) was heated using microwave irradiation to 100° C. for 30 min. The reaction mixture was concentrated in vacuo and the residue was purified by preparative HPLC to provide Compound IIa (46 mg). 1H NMR delta (ppm) (CHCl3-d): 7.77-7.70 (4H, m), 7.56-7.46 (7H, m), 7.37 (1H, s), 5.97 (2H, s), 3.91 (3H, s). LCMS (10 cm_ESCI_Bicarb_MeCN) Rt 3.88 min; m/z 401 [M+H] 94.62percent purity.

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

Reference:
Patent; BUeRLI, Roland Werner; ESMIEU, William Rameshchandra Krishna; LOCK, Christopher James; MALAGU, Karine Fabienne; OWENS, Andrew Pate; HARTE, William E.; US2014/121197; (2014); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 492-98-8, 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. 492-98-8, name is 1H,1’H-2,2′-Biimidazole belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

Example 16: Synthesis of (tetrakis(2-phenylpyridinato)(mu-biimidazolyl) diiridium(III), Abbreviation; [Ir(ppy)2BIm]2) [0307] [0308] Under argon atmosphere, into a 100 mL Schlenk flask equipped with a stirrer were placed 322 mg (0.30 mmol) of di-mu-chloro-tetrakis(2-phenylpyridinato) diiridium(III), 40 mg (0.30 mmol) of 2,2′-biimidazole and 60 ml of tetrahydrofuran. And then, the mixture was stirred at room temperature for 13 hours. Subsequently, 83 mg (0.63 mmol) of tert-butoxy potassium (t-BuOK (85 wt% product)) was added to the mixture, and the mixture was reacted under stirring at room temperature for 24 hours. After the completion of the reaction, tetrahydrofuran was distilled off under reduced pressure, and then methylene chloride was added to the residue, and the insoluble substance was removed by filtration. The filtrate was concentrated under reduced pressure. The resultant crude reaction product was subjected to column chromatography with alumina (developing solvent: methylene chloride / hexane (volume ratio; 3/1) : 0.5 % triethylamine) for purification, to provide 113 mg of the desired compound as a yellow solid. (Yield: 33 %) The desired compound obtained was a mixture of isomers, and the product ratio was Isomer 1 (main product) : Isomer 2 = 61:39. [0309] Additionally, tetrakis(2-phenylpyridinato)(mu-biimidazolyl) diiridium(III) was a novel compound, which had the following properties: [0310] 1H-NMR (400MHz, C4D8O, delta (ppm)) Isomer 1; 8.18 (dd, 4H), 7.86 (d, 4H), 7.70-7.55 (m, 8H), 6.81-6.72 (m, 8H), 6.66-6.62 (m, 4H), 6.38 (dd, 4H), 6.11 (s, 4H) Isomer 2; 7.92 (d, 4H), 7.78 (dd, 4H), 7.70-7.55 (m, 8H), 6.81-6.72 (m, 8H), 6.66-6.62 (m, 4H), 6.32 (dd, 4H), 6.13 (s, 4H) FD-MS (M/Z): 1132 M+

The synthetic route of 1H,1’H-2,2′-Biimidazole has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Ube Industries, Ltd.; FUJIMURA, Osamu; FUKUNAGA, Kenji; IWASA, Takafumi; TANAKA, Yasuhiro; FUJITA, Harunori; MURAKAMI, Tadashi; HONMA, Takashi; MACHIDA, Toshikazu; KASHIHARA, Natsuko; EP2647642; (2013); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 68282-47-3, 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. 68282-47-3, name is 2-Phenyl-1H-imidazole-4-carbaldehyde belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

COMPOUND 12.1.58: N,N-DIETHYL-4-{5,6,7-TRIMETHOXY-2-[(2-PHENYL- 1H-IMIDAZOL-5-YL)METHYL]-1,2,3,4-TETRAHYDROISOQUINOLIN-1- YLIBENZAMIDE; 2-Phenyl-imidazole-4-carboxyaldehyde (92.6 mg, 0.54 mmol) was added to a solution of INTERMEDIATE 5.1. 16 (107.7 mg, 0.27 mmol) in 1,2-dichloroethane (5 mL) and the reaction mixture stirred at room temperature for 10 min. Sodium triacetoxyborohydride (400 mg, 1.89 mmol) was added followed by N-methyl-2- pyrrolidinone (350 pL) and the reaction mixture stirred at RT for 16 h. 1 N NaOH (5 mL) was added and the organic solvent removed in vacuo. The residue was extracted with EtOAc (3 x 20 mL) and the organic layer washed with water (20 mL). The organic layer was concentrated in vacuo and the residue purified by flash chromatography on SiOx column (EtOAc: MeOH 95: 5) to afford COMPOUND 12.1. 58 as an oil (33 mg, 22%). lH NMR (500 MHz, CDC13) : 8 1.10 (br s, 3H), 1.24 (br s, 3H), 2.63 (m, 1H), 2.76 (m, 2H), 3. 10 (m, 1H), 3.26 (br s, 2H), 3.57 (s, 3H), 3.51-3. 62 (m, 4H), 3.84 (s, 3H), 3. 88 (s, 3H), 4.65 (s, 1H), 5.98 (s, 1H), 6.91 (s, 1H), 7.25-7. 35 (m, 7H), 7.87 (d, J 8.5 Hz, 2H) ; 13C NMR (125 MHz, CDCl3) : 6 13.12, 14.45, 22. 51, 39.70, 43.67, 46.18, 49.68, 56.09, 60.70, 61.03, 66. 58, 107.94, 121.56, 125.43, 126.50, 128.46, 128.90, 129.91, 130. 76, 132. 78,136. 08,140. 72,144. 76, 146.76, 147.07, 150. 89, 151. 73, 171.64 ; (+) LRESIMS m/z 555.25 [M+H]+.

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

Reference:
Patent; ASTRAZENECA AB; WO2005/61484; (2005); 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. 124312-73-8, name is (1-Methyl-1H-imidazol-2-yl)methanamine, This compound has unique chemical properties. The synthetic route is as follows., name: (1-Methyl-1H-imidazol-2-yl)methanamine

Method B. A solution of 8 (0.247 g, 1.17 mmol) in MeOH (20 mL) was treated sequentially with 2-aminomethyl-1-methylimidazole (0.059 g, 0.53 mmol) and NaBH3CN (0.07 g, 1 mmol). The reaction mixture was stirred at room temperature overnight and the solvent was removed under vacuum yielding L2 a yellow oil. The crude product was purified as described in method A with similar isolated yields. IR (KBr) 3052 cm-1 (amide-NH), 1667 cm-1 (amide-C=O); 1H NMR CD2Cl2 delta 7.81 (s, AmIm(N-H)), 7.09 (s, 2, AmIm(H-5)), 6.80 (s, 1, Im(H-5)), 6.75 (s, 1, Im(H-4)), 3.60 (s, 2, Im(-CH2)), 3.57 (s, 4, AmIm(CH2)), 3.07 (s, 3, Im(-CH3)), 3.02 (s, 6, AmIm(-CH3)), 1.18 (s, 18, AmIm(-C(CH3)3)). 13C NMR delta 174.1, 169.7 (s, AmIm(-C=O)), 145.4 (s,Im(C2)), 141.2 (s, AmIm(C2)), 135.5 (s, AmIm(C4)), 126.4 (s,Im(C5)), 120.8 (s, Im(C4)), 107.9 (s, AmIm(C-5)), 47.8 (s, Im(-CH2-), AmIm(-CH2-)), 38.0 (s, AmIm(C(CH3)3), 31.1 (s, Im(CH3)), 28.9 (s, AmIm(C(CH3)3); HRMS calcd for C25H40N9O2, 498.3305 [M+H+], found 498.3311.

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 124312-73-8.

Reference:
Article; Cheruzel, Lionel E.; Cui, Jinlan; Mashuta, Mark S.; Grapperhaus, Craig A.; Buchanan, Robert M.; Tetrahedron Letters; vol. 52; 37; (2011); p. 4771 – 4774;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 26663-77-4,Some common heterocyclic compound, 26663-77-4, name is Methyl benzimidazole-5-carboxylate, molecular formula is C9H8N2O2, 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.

REFERENCE EXAMPLE 8 (+)-4,5,6,7-tetrahydrohenzimidazole-5-carboxylic acid hydrochloride Methyl benzimidazole-5-carboxylate was subjected to catalytic reduction according to the method described in CROATICA CHEMICA ACTA 45, 297-312 (1973), to obtain methyl 4,5,6,7-tetrahydrobenzimidazole-5-carboxylate.

The synthetic route of 26663-77-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Tokyo Tanabe Company Limited; US5677326; (1997); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem