Month: June 2021

Related Products of 288-32-4, A common heterocyclic compound, 288-32-4, name is 1H-Imidazole, molecular formula is C3H4N2, 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.

Comparative Example 1; Preparation of 2-(1H-imidazol-1-yl)acetic acid (Process Related to WO2005/063717)Reaction flask was charged with imidazole (50 g), dimethylformamide (20 ml), toluene (200 ml), potassium carbonate (90 g) and potassium iodide (5 g). The mixture was stirred for 10 min and methyl chloroacetate (120 g, 97 ml) was added at 25-30 C. over 1.5 hr. The mixture was stirred for 1 hour at 25-30 C., heated to 60-65 C. and was stirred at this temperature for additional 3 hours. The mixture was cooled down to room temperature and ethyl acetate (100 ml) was added. The mixture was stirred for 20 min and upper organic layer was decanted. Ethyl acetate (100 ml) was added to the residue and the mixture was stirred for 20 min. Upper organic layer was decanted and combined with the first one. Water (100 ml) was added to the residue and the mixture was stirred for 30 min. Inorganic salts were filtered off to give after drying 72.6 g of dry cake (content of diacid in dry inorganic cake was 5.8 g (represents 4.3% of theoretical yield). The filtrate was extracted with ethyl acetate (2×100 ml). Aqueous phase 152 ml contain 24.1 g of the diacid (represents 17.8% of theoretical yield). The ethyl acetate layers were combined with previous extracts. Combined ethyl acetate extracts were evaporated to give 50.5 g of brownish oil.

The synthetic route of 288-32-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Kas, Martin; Benes, Michal; Pis, Jaroslav; US2010/130746; (2010); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 104619-51-4, 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 104619-51-4 as follows.

A solution containing the product from step 1 (8.36 g, 54.2 mmol) and 2-amino-4-nitrophenol (8.74 g, 54.2 mmol) in anhydrous THF (200 mL) was allowed to reflux under N2 for 14 hours. The mixture was cooled to RT, filtered, and the precipitate was washed with THF (cold) then dried in vacuo to afford the desired product (9.0 g), as a yellow solid. MS (ESI) m/e (M+H+): 180. 1H NMR (DMSO) delta: 7.857.96 (m, 3H), 7.52 (d, J=8.8 Hz, 1H).

According to the analysis of related databases, 104619-51-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Merck Sharp & Dohme Corp.; Coburn, Craig A.; Ludmerer, Steven W.; Liu, Kun; Wu, Hao; Soll, Richard; Zhong, Bin; Zhu, Jian; (155 pag.)US2019/127365; (2019); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 288-32-4,Some common heterocyclic compound, 288-32-4, name is 1H-Imidazole, molecular formula is C3H4N2, 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.

Benzoyl chloride (4.99 g, 35.5mmol) wasadded dropwise to a solution of imidazole (4.83 g, 7.1mmol)in dichloromethane (25 mL). The reaction mixture wasstirred for 3 h, and the resulting precipitate was removedby filtration. The filtrate was washed with cold water (<=5 C,10mL x 3) and concentrated under reduced pressure. Theresidue was purified by bulb-to-bulb distillation (heatertemperature: 160 C, 80 mmHg) to yield 1c (4.33 g, 71%yield) as colorless liquid. 1HNMR (400 MHz, CDCl3,26 C): /ppm 8.07 (t, J = 1.0 Hz, 1H, f ), 7.817.79(m,2H, a), 7.69 (tt, J1 = 7.4 Hz, J2 = 1.8 Hz, 1H, c), 7.587.54(m, 3H, b and d), 7.16 (dd, J1 = 1.8 Hz, J2 = 1.0 Hz, 1H, e). The synthetic route of 288-32-4 has been constantly updated, and we look forward to future research findings. Reference:
Article; Kohsaka, Yasuhiro; Homma, Kazumasa; Sugiyama, Susumu; Kimura, Yoshikazu; Chemistry Letters; vol. 47; 1; (2018); p. 100 – 102;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Some common heterocyclic compound, 7098-07-9, name is 1-Ethyl-1H-imidazole, molecular formula is C5H8N2, 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 1-Ethyl-1H-imidazole

Step 1: 341 parts of 1-ethylimidazole (manufactured by Tokyo Chemical Industry Co., Ltd.), 319 parts of dimethyl carbonate (manufactured by Tokyo Chemical Industry Co., Ltd.) and 340 parts of methanol (Tokyo Chemical Industry Co., Ltd.) were charged in a stainless steel autoclave equipped with a reflux condenser, And dissolved. Then, the temperature was raised to 140 ° C. The reaction was carried out at a pressure of 0.8 MPa for 30 hours. 1 H-NMR analysis of the reaction product revealed that 1-ethyl-3-methylimidazolium monomethyl carbonate was formed.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 7098-07-9, its application will become more common.

Reference:
Patent; SANYO CHEMICAL INDUSTRIES LIMITED; SATOU, YOSHIMI; MURATA, SHINICHI; SEIKE, HIDEO; (20 pag.)JP5848690; (2016); B2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

These common heterocyclic compound, 75370-65-9, name is 4-Amino-1H-benzo[d]imidazol-2(3H)-one, 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. name: 4-Amino-1H-benzo[d]imidazol-2(3H)-one

4-(aminomethyl)-N,N-dimethylbenzenamine 2i (1 g, 6.9 mmol) was dissolved in 40 ml of AcOEt and at 0C triphosgene (2 g, lequiv.) was added to the solution. The mixture was warmed at 80C for 4 hours then evaporated and the residue was dissolved in 20 ml of DMF. The solution of the isocyanate was added dropwise to a solution in DMF (10 ml) of compound la (1 g, 6.9 mmol) and the mixture was warmed at 80C for 8 hours. (TLC AcOEt). The solvent was evaporated and the crude was dissolved in AcOEt (50 ml) and washed with water (1 X 30 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 350 mg of a white solid. Yield = 16% 1HNMR (DMSO, 200 MHz) delta 2.51 (6H, s), 4.18 (2H, d, J = 5.6 Hz), 6.58 (2H, m), 6.69 (2H, d, J = 8.8 Hz), 6.86 (2H, m), 7.14 (2H, d, J = 8.8 Hz), 8.18 (1H, s), 9.98 (1H, bs), 10.58 (1H, bs); [M+1] 326.5 (C17H19N5O2 requires 325.37).

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.; NAPOLETANO, Mauro; TREVISANI, Marcello; PAVANI, Maria Giovanna; FRUTTAROLO, Francesca; WO2011/120604; (2011); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 288-32-4, 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. 288-32-4, name is 1H-Imidazole belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

1. To a solution of 1 (20 g, 108.1 mmol) in dry DMF (200 mL) were added lH-imidazole (8.1 g, 118.9 mmol), Cs2C03 (38.7 g, 118.9 mmol), Cul (2 g), 18-Crown-6 (2 g). The resulting solution was stirred at 80 C for 24 h. The mixture was cooled to RT, treated with water and extracted with EA. The combined extracts were washed with water, brine, dried over anhydrous Na2S04, filtered and concentrated to give a crude oil. The crude product was purified by recrystallization to afford 2 (1 1 g, 59.2 %).

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

Reference:
Patent; FORGE LIFE SCIENCE, LLC; REMISZEWSKI, Stacy; CHIANG, Lillian W.; MURPHY, Eain Anthony; KAYSER, Frank; SUN, Qun; FINK, Sarah Jocelyn; (128 pag.)WO2019/79519; (2019); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

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 33468-69-8 as follows. Product Details of 33468-69-8

Preparation of 2-[3-ethylsulphanyl-5-(trifluoromethyl)-2-pyridyl]-3-methyl-6-[4-(trifluoromethyl)-imidazol-1-yl]imidazo[4,5-c]pyridine (I-74) Under argon, 99 mg (0.27 mmol) of 6-chloro-2-[3-ethylsulphanyl-5-(trifluoromethyl)-2-pyridyl]-3-methylimidazo[4,5-c]pyridine, 23 mul (0.15 mmol) of trans-N,N’-dimethylcyclohexane-1,2-diamine, 6.8 mg (36 mumol) of copper(I) iodide, 30 mg (0.22 mmol) of 4-(trifluoromethyl)-1H-imidazole and 64 mg (0.46 mmol) of potassium carbonate are added to 1 ml of degassed toluene. The vessel is closed and the reaction mixture is heated in a CEM Discover microwave reactor to 110 C. for 4 h. After cooling to room temperature, ethyl acetate is added and the mixture is filtered through a Celite bed, which is subsequently rinsed with ethyl acetate. The solvent is removed under reduced pressure and the residue is separated chromatographically by MPLC on silica gel (gradient: ethyl acetate/cyclohexane). In this way, 22 mg (100% purity, 18% yield) of 2-[3-ethylsulphanyl-5-(trifluoromethyl)-2-pyridyl]-3-methyl-6-[4-(trifluoromethyl)imidazol-1-yl]imidazo[4,5-c]pyridine are obtained. (log P (neutral): 3.36; MH+: 473; 1H NMR (600 MHz, CD3CN) delta ppm: 8.905 (3.0); 8.903 (3.0); 8.852 (1.6); 8.850 (1.6); 8.500 (1.9); 8.313 (1.5); 8.311 (2.1); 8.309 (1.4); 8.183 (1.7); 8.181 (1.7); 7.962 (3.4); 7.961 (3.4); 4.001 (16.0); 3.940 (0.4); 3.124 (1.1); 3.111 (3.4); 3.099 (3.5); 3.087 (1.2); 2.639 (0.7); 2.184 (55.7); 2.109 (1.2); 2.005 (2.2); 1.998 (195.7); 1.989 (2.7); 1.985 (1.8); 1.981 (10.0); 1.977 (18.2); 1.973 (26.5); 1.969 (18.0); 1.965 (9.0); 1.882 (1.2); 1.419 (0.4); 1.404 (0.7); 1.373 (0.6); 1.330 (4.1); 1.318 (9.0); 1.309 (1.6); 1.305 (5.2); 1.301 (3.4); 0.914 (0.6).

According to the analysis of related databases, 33468-69-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BAYER CROPSCIENCE AKTIENGESELLSCHAFT; FISCHER, Ruediger; ALIG, Bernd; ILG, Kerstin; MALSAM, Olga; GOeRGENS, Ulrich; TURBERG, Andreas; LI, Jun; ZHERSH, Sergey; ARLT, Alexander; (58 pag.)US2017/73342; (2017); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Some common heterocyclic compound, 36947-68-9, name is 2-Isopropyl-1H-imidazole, molecular formula is C6H10N2, 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 2-Isopropyl-1H-imidazole

General procedure: To a stirred solution of indole (1.0 mmol)/Imidazole (1.2 mmol) in DMSO was added 1,3-diyne (1.0 mmol), CuI (0.1 mmol), 1,10-phenanthroline (0.05 mmol) and cesium carbonate (1.5 mmol). The reaction mixture was heated at 100 C for 5-16 h and the completion of the reaction was monitored by TLC. After completion of the reaction, it was cooled down to room temperature and then diluted with H2O (5 mL) followed by extraction of the product with EtOAc (3 × 10 mL). The combined organic layer was washed with brine, dried over anhydrous Na2SO4 and the solvent was removed in vacuo. The crude product was purified on a silica gel column using hexane: ethyl acetate as eluent. The Z isomer was crytalised using DCM/EtOH in indole and EtOH in case of imidazole.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 36947-68-9, its application will become more common.

Reference:
Article; Gupta, Sahaj; Agarwal, Piyush K.; Saifuddin, Mohammad; Kundu, Bijoy; Tetrahedron Letters; vol. 52; 44; (2011); p. 5752 – 5757;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

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 15469-97-3 as follows. HPLC of Formula: C22H18N2

Compounds 6 and 7: To a solution of tritylimidazole (2.67 g, 8.6 mmol) in THF (85 ml) cooled to -20 C a stock 1.6 M solution n-butyl lithium in hexanes (5.13 ml, 8.2 mmol) was added dropwise. The resulting wine red coloured solution was allowed to warm up to RT and stirred for 30 min. The solution was then cooled to -78 C and a solution of aldehyde (4.17 g, 7.8 mmol) in THF (15ml) was added dropwise. The resulting solution was stirred for 30 min and then allowed to warm to RT in 30 min. The reaction was quenched by addition of ammonium chloride solution and extracted with ethyl acetate. The aqueous layer was extracted with ethyl acetate once more. The combined organic layer was dried and evaporated. The residue was purified by flash column chromatography in PE-EA gradient 10-20-30percent to give 1.18 g (1.4 mmol, 18percent) of 6 (Rf = 0.55 PE- EA 20percent) and 3.48 g (4.13 mmol, 53percent) of 7 (Rf = 0.4 PE-EA 20percent) .6: [?]D = -10.5 c 1.24 CHCl3HRMS: Positive mode, m/z = 845.4344; expected for C54H6IN2O5Si [M+H]+ = 845.4350.?H (500 MHz) : 0.0 and 0.02 (6H, 2*s, -Si (CH3) C (CH3) 3) , 0.89 (9H, s, -Si(CH3)C(CH3)S) , 2.94 (IH, dd, J4, 5 = 6.5 Hz, J4/3 = 4.1 Hz, H-4) , 3.1 (IH, bs, 2-OH) , 3.14 (IH, dd, J6a,5 = 5.4, Jea,6b = 10.2 Hz, H-6a) , 3.37 (IH, dd, J6b,5 = 3 Hz, H- 6b) , 3.8 (IH, dd, J3, 2 = 3.2 Hz, H-3) , 3.93 (IH, ddd, H-5) , 3.97 and 4.41 (2H, AB spectrum, Jgem = 11.5 Hz, PhCH2O-) , 4.3 (IH, bs, H-2) , 4.33 (2H, s, PhCH2O-) , 4.71 and 4.93 (2H, AB spectrum, Jgem = 11.2 Hz, PhCH2O-) , 6.78 (IH, m) , 7.02 (2H, m) , 7.13-7.4 (28H, m) .?c (125 MHz) : -4.4, 18.2, 26.1, 66.6 (C-2) , 72.8 (C-6) , 72.9 (C-5) , 73.2, 73.8, 74.4, 75.3, 78.8 (C-3) , 81.7 (C-4) , 122.2, 126.08, 127.06, 127.3, 127.4, 127.8, 128.1, 128.3, 128.5, 130, 138.6, 138.8, 138.9, 142.9, 150.7.7: [?]D = -67.5 c 1.34 CHCl3HRMS: Positive mode, m/z = 845.4344; expected for C54H6IN2O5Si [M+H]+ = 845.4350.?H (500 MHz) : -0.09 and 0.0 (6H, 2*s, -Si (CH3) C (CH3) 3) , 0.82 (9H, s, -Si (CH3) C (CH3) 3) , 3.52 (IH, dd, J6a,5 = 6.5 Hz, J6a,6b = 10.4 Hz, H-6a) , 3.73 (IH, dd, J4, 5 = 7.3, J4, 3 = 2.6 Hz, H- A) 1 3.78 (IH, dd, J6b,5 = 2.2 Hz, H-6b) , 4.12 (IH, ddd, J5, 4 =6.7 Hz, H-5) , 4.24 (IH, dd, J3, 2 = 8.7 Hz, H-3) , 4.27 and 4.57 (2H, AB spectrum, Jgem = 12.4 Hz, PhCH2O-) , 4.41 (2H, s, PhCH2O-) , 4.48 and 4.6 (2H, AB spectrum, Jgem = 10.7 Hz, PhCH2O-) , 4.5 (IH, dd, J2, 0H = 4 Hz, H-2) , 6.79 (IH, m) , 6.85-7.4 (31H, m) .?c (125 MHz) : -4.7, 18.2, 26, 65.9 (C-2) , 72.6 (C-5) ,73.1, 73.2 (C-6) , 73.8, 75.5, 79.6 (C-4) , 80.13 (C-3) , 122.3, 125.9, 126.17, 126.5, 127, 127.2, 127.6, 127.8,127.9, 128.1, 128.4, 128.6, 130, 130.2, 138.7, 139, 139.3, 141, 142.5, 150.2 (C-I) .

According to the analysis of related databases, 15469-97-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; THE UNIVERSITY COURT OF THE UNIVERSITY OF DUNDEE; WO2008/59267; (2008); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 152628-02-9, These common heterocyclic compound, 152628-02-9, name is 1,7′-Dimethyl-2′-propyl-1H,1’H-2,5′-bibenzo[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.

General procedure: A solution of an appropriate benzimidazole (5.03mmol) and NaH (0.12g, 5.53mmol, 60%) in 100mL anhydrous THF was stirred for 30minat 50C. After cooling to rt, a mixture of an appropriate bromide (6.04mmol) in anhydrous THF (50mL) was added dropwise to the solution. The solution was stirred for 3hat 50C. Then the resulting mixture was poured into 30mL ice water, and extracted with ethyl acetate (50mL×3). The combined organic layer was dried over MgSO4. After filtration, the solvent was removed under reduced pressure and the residue was purified by CC to give the product as white solid 4.1.7.3 [4-[[2-Propyl-4-methyl-6-(1-methylbenzimidazol-2-yl)benzimidazole-1-yl]methyl]-1H-indol-1-yl](phenyl)methanone (12c) 12c was prepared by following the above general procedure. Yield: 91.9%. MP: 214-216 C. 1H NMR (400 MHz, CDCl3): delta 8.34 (d, 1H), 8.04 (s, 1H), 7.27-7.73 (m, 12H), 6.74 (d, 1H), 6.52 (d, 1H), 5.67 (s, 2H), 3.89 (s, 3H), 2.89 (t, 2H), 2.78 (s, 3H), 1.85 (m, 2H), 1.02 (t, 3H). MS (ESI): [M + H]+ calcd 538.3; found 538.3.

The synthetic route of 152628-02-9 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Zhu, Weibo; Bao, Xiaolu; Ren, He; Da, Yajing; Wu, Dan; Li, Fuming; Yan, Yijia; Wang, Li; Chen, Zhilong; European Journal of Medicinal Chemistry; vol. 115; (2016); p. 161 – 178;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem