Month: May 2021

Synthetic Route of 151414-47-0,Some common heterocyclic compound, 151414-47-0, name is 2,6-Difluoro-4-methoxyaniline, molecular formula is C7H7F2NO, 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.

To a solution of intermediate 2b (72 mg) in dry toluene (2 mL) were consecutively added 2,6-difluoro-4-methoxyaniline (48 mg) and trimethyl aluminium (2 M in heptane, 0.15 mL) and the resulting mixture was heated to 110 C. for 1 h. The mixture was chilled and 1 M HCl (2 mL) was added. The layers were separated and the aqueous layer was extracted with EtOAc. The combined organic layers were dried and the volatiles were removed under reduced pressure. The residue was purified through washing with Et2O to give the desired compound (86% yield). [0510] LC-MS (Method 2): m/z [M+H]+=404.1 (MW calc.=403.38); Rt=0.74 min.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2,6-Difluoro-4-methoxyaniline, its application will become more common.

Reference:
Patent; Gruenenthal GmbH; Nordhoff, Sonja; Wachten, Sebastian; Kless, Achim; Voss, Felix; Ritter, Stefanie; US2014/194452; (2014); A1;,
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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. 151414-47-0, name is 2,6-Difluoro-4-methoxyaniline, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 2,6-Difluoro-4-methoxyaniline

Step A: Preparation of 1 -(2,6-difluoro-4-methoxyphenyl)-2-propanoneTo a mixture of concentrated sulfuric acid (15.6 g, 159 mmol) in water (75 mL) at 0 C was added 2,6-difluoro-4-methoxybenzenamine (12.4 g, 78.0 mmol), followed by sodium nitrite (6.65 g, 81.7 mmol) in water (30 mL) while maintaining the reaction temperature below 10 C. After 45 minutes, isopropenyl acetate (16.4 g, 164 mmol) was added to the reaction mixture followed by copper(II) sulfate pentahydrate (0.982 g, 3.90 mmol). After an additional 30 minutes, a solution of sodium sulfite (4.91 g, 38.9 mmol) in water (60 mL) was added to the reaction mixture while maintaining the temperature below 10 C. The reactionmixture was allowed to warm to room temperature, stirred for 3 h and then sodium sulfite (0.5 g, 3.97 mmol) was added in three portions. The resulting mixture was extracted with hexanes (2 x 300 mL) and the combinded organic layers were washed with sodium hydroxide (0.5 N) (5 x 100 mL) and water (100 mL). The organic layer was dried over magnesium sulfate, filtered and concentrated under reduced pressure to provide the titlecompound (6.19 g).

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 151414-47-0.

Reference:
Patent; E. I. DU PONT DE NEMOURS AND COMPANY; TAGGI, Andrew, Edmund; BEREZNAK, James, Francis; LONG, Jeffrey, Keith; WO2014/130241; (2014); A1;,
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These common heterocyclic compound, 10075-63-5, name is 1,5-Dimethoxynaphthalene, 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. Formula: C12H12O2

Methansulfonate 17. 5 part pentoxide diphosphorus 1. 75 part is added, with stirring at 23 C 30 minutes. The mixture obtained, eq. (I-44-a) compound represented by 3. 49 part is prepared, and then, is cooled to 0 C, eq. (I-44-b) compound represented by 5. 5 portion 92 by applying a dropped. After 20 minutes under stirring 0 C, further 23 C 18 at a time. The obtained reaction liquid is cooled to 0 C, ion exchange water 27. 03 part stocking, thereafter, 28% ammonia water 11. 07 by adding a neutralizing, represented by soln. contg. eq. (I-56) is obtained. A solution containing a salt eq. (I-56), eq. (I-44-c) compound represented by 7. 90 part and chloroform 78. 96 by adding, 24 hours at 23 C, a liquid. The organic layer, 40 parts of ion-exchanged water to mixing, stirring, liquid. This flush to 5 times. The organic layer, activated carbon 1. 00 part a, 30 minutes stirring at 23 C, filtration. The filtered liquid is concentrated, obtd. tert-butyl methyl ether 80 to the residue aminoacetonitrile 3 part is added and part, by concentrating the supernatant liquid is removed, the salt 7 eq. (I-44). 83 part is obtained.

The synthetic route of 1,5-Dimethoxynaphthalene has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SUMITOMO CHEMICAL COMPANY LIMITED; ANRYU, YUKAKO; ICHIKAWA, KOJI; YOSHIDA, MASAFUMI; (86 pag.)JP2015/143208; (2015); A;,
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Related Products of 17600-72-5,Some common heterocyclic compound, 17600-72-5, name is 1-Ethoxy-2-methoxybenzene, molecular formula is C9H12O2, 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: To a stirred solution of aryl methyl ether (20 mmol) and 47% aqueous HBr (4.5 mmol equiv. of substrate) added Aliquat-336 (10 wt. % of substrate) in a single lot. The resulting reaction mixture was heated at 105±5 C, and the progress of reaction was monitored by TLC. After completion of reaction, the reaction mixture was cooled to room temperature and quenched by adding water (25 ml). The resulting reaction mass was extracted with 3×30 ml ethyl acetate. Ethyl acetate layer washed twice with 20 ml of water, dried over anhydrous Na2SO4 and evaporated under reduced pressure. The crude product was purified by silica gel column chromatography using ethyl acetate/hexane system.

The synthetic route of 17600-72-5 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Waghmode, Suresh B.; Mahale, Ganesh; Patil, Viraj P.; Renalson, Kartik; Singh, Dharmendra; Synthetic Communications; vol. 43; 24; (2013); p. 3272 – 3280;,
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Related Products of 456-55-3,Some common heterocyclic compound, 456-55-3, name is (Trifluoromethoxy)benzene, molecular formula is C7H5F3O, 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.

(iv) 4-Trifluoromethoxy-alpha,alpha,alpha-trifluoroacetophenone, from 4-bromotrifluoromethoxybenzene 4-Bromotrifluoromethoxybenzene may be prepared from trifluoromethoxybenzene by the process described in the Journal of Organic Chemistry, 29, 1, (1964). Boiling point: 164-166 C. (atmosphere pressure). 1 H NMR (CDCl3) (ppm): 7.35, 8.14 (4H,d) 19 F NMR (CDCl3) (ppm relative to CFCl3): -58.1 (s) CF3 O -72.1 (s) CF3

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route (Trifluoromethoxy)benzene, its application will become more common.

Reference:
Patent; Imperial Chemical Industries PLC; US5225607; (1993); A;,
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Ether | (C2H5)2O – 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. 888318-22-7, name is 1-Bromo-3,4-difluoro-2-methoxybenzene, This compound has unique chemical properties. The synthetic route is as follows., COA of Formula: C7H5BrF2O

To a flask containing 1-bromo-3,4-difluoro-2-methoxy-benzene (1.0 g, 4.48 mmol) and 1,4-dioxa-8-azaspiro[4.5]decane (0.71 g, 4.93 mmol) in 1,4-dioxane (10 ml) was added tBuONa (1.3 g, 13.44 mmol), Pd2(dba)3 (82 mg, 0.09 mmol) and Ru-Phos (84 mg, 0.18 mmol)under N2. After being heated with stirring at 100 C overnight, the reaction mixture was cooled to rt, diluted with water (20 mL) and extracted with EA (30 mL) for three times. The combined organic layer was washed with brine, dried over anhydrous Na2SO4 and concentrated in vacuo to give 8- (3 ,4-difluoro-2-methoxy-phenyl)- 1 ,4-dioxa- 8-azaspiro [4.5] decane (0.74 g), which was used in the next step without further purification.

According to the analysis of related databases, 888318-22-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; CHENG, Zhanling; WANG, Min; YANG, Song; (208 pag.)WO2016/107832; (2016); A1;,
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Adding a certain compound to certain chemical reactions, such as: 17715-70-7, name is 2,4-Dimethoxy-1-fluorobenzene, belongs to ethers-buliding-blocks 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 17715-70-7, HPLC of Formula: C8H9FO2

A solution of 1-fluoro-2,4-dimethoxybenzene (0.25 g, 1.60 mmol) in 5 mL of CH2Cl2 under Ar atmosphere was cooled to 0 C, then TiCl4 (neat, 0.38 mL, 3.52 mmol) was slowly added. The reaction mixture was left to react for 30 min. Dichloromethyl methyl ether (0.21 mL, 2.40 mmol) was added and the mixture left to react for a further 30 min. The reaction was quenched by the addition of saturated aq. NH4Cl (10 mL) and diluted with CH2Cl2 (10 mL). The mixture was left to stand for 30 min and the organic phase was separated and washed with 0.1 M HCl, saturated aq. NaHCO3 and brine. The organic layer was dried with Na2SO4, filtered and concentrated in vacuo to give crude product which was purified by PTLC with 30% EtOAc/hexanes as eluent to give 5-fluoro-2,4-dimethoxybenzaldehyde as a white solid (0.24 g, 1.30 mmol, 88 %).

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; Radomkit, Suttipol; Sarnpitak, Pakornwit; Tummatorn, Jumreang; Batsomboon, Paratchata; Ruchirawat, Somsak; Ploypradith, Poonsakdi; Tetrahedron; vol. 67; 21; (2011); p. 3904 – 3914;,
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Reference of 121588-79-2, These common heterocyclic compound, 121588-79-2, name is trans-4-Methoxycyclohexanamine, 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.

To a DMF (2 mL) solution of (trans)- 3-(5-fluoro-2- methoxyphenoxy)cyclobutanecarboxylic acid (Intermediate 69) (50 mg, 0.21 mmol) was added HATU (1 19 mg, 0.312 mmol) and N,N-diisopropylethylamine (0.1 1 mL, 0.62 mmol). After 10 minutes, 4-((frans)-4-aminocyclohexyl)morpholin-3-one (Intermediate 73) (41 mg, 0.21 mmol) was added, and the mixture was stirred for 2 h, diluted with water and MeOH, and loaded onto a semi-prep HPLC (NH4OH as modifier) to afford the title compound as a light tan solid (43 mg, 49%). 1H NMR (400 MHz, CD3OD) delta 1 .26-1 .41 (m, 2 H), 1 .60-1 .70 (m, 4 H), 1 .90-1 .99 (m, 2 H), 2.29-2.41 (m, 2 H), 2.59 (ddd, J = 13, 7, 4 Hz, 2 H), 3.04 (dt, J = 10, 5 Hz, 1 H), 3.27 (dt, J = 3, 2 Hz, 2 H), 3.29-3.34 (m, 2 H), 3.56-3.62 (m, 1 H), 3.77 (s, 3 H), 3.80-3.86 (m, 2 H), 4.08 (s, 2 H), 4.25-4.34 (m, 1 H), 6.48-6.61 (m, 2 H), 6.87 (dd, J = 9, 5 Hz, 1 H); LC-MS (LC-ES) M+H = 421 .

The synthetic route of 121588-79-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; DEATON, David Norman; GUO, Yu; HANCOCK, Ashley Paul; SCHULTE, Christie; SHEARER, Barry George; SMITH, Emilie Despagnet; STEWART, Eugene L.; THOMSON, Stephen Andrew; (556 pag.)WO2018/69863; (2018); A1;,
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Ether | (C2H5)2O – PubChem

13353-03-2, name is 2,4,6,8-Tetraoxanonane, belongs to ethers-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. Application In Synthesis of 2,4,6,8-Tetraoxanonane

2.7 mol of dimethoxymethoxymethane, 0.5 mol of 2,6-methylethylaniline and 100 mLBenzene was added to the reaction flask and incubated at 75-80 C for 18 h.After the completion of the reaction, the methoxymethanol and benzene recovered were separated and separated.Distillation gives 2,6-methyl-N-(methoxymethoxymethyl)aniline,The yield was 97.2% and the content was 98.9%.The total yield of the above two steps was 93.51%.

The synthetic route of 13353-03-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Shandong Binnong Technology Co., Ltd.; Xu Jiajun; Sheng Qingquan; Zhang Jun; (7 pag.)CN110183334; (2019); A;,
Ether – Wikipedia,
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Adding a certain compound to certain chemical reactions, such as: 172282-50-7, name is 4-(Difluoromethoxy)benzene-1,2-diamine, belongs to ethers-buliding-blocks 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 172282-50-7, Safety of 4-(Difluoromethoxy)benzene-1,2-diamine

Dissolve 8.1 g of 4-difluoromethoxy-o-phenylenediamine in 30 mL of methanol, directly add 35 mL of carbon disulfide and 3.0 g of sodium hydroxide, stir, heat to reflux, and hold for 4 h.Reduce the temperature to room temperature, add 30ml of water, then adjust the pH value to 4 with 10% hydrochloric acid, flocculent precipitates appear, and filter to obtain the crude 2-mercapto-5-difluoromethoxybenzimidazole.Add the obtained crude 2-mercapto-5-difluoromethoxybenzimidazole to a 100 mL flask, and then add 3.0 g of sodium hydroxide, 30 mL of water and 1 g of activated carbon, heat to 80 C, and hold for 1 h.Hot filtration. When the temperature of the filtrate drops to room temperature, adjust the pH value to 4 with a concentration of 10% hydrochloric acid, flocculent precipitates appear, filter,The obtained solid (precipitation) was washed with water to neutrality and dried to obtain a white solid product, 2-mercapto-5-difluoromethoxybenzimidazole, with a yield of 94.5%, a melting point of 260.1-261.5 C, and a purity of more than 99%.

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-(Difluoromethoxy)benzene-1,2-diamine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Anhui Jin He Industrial Co., Ltd.; Jiang Weiqiang; Chen Chaohui; Sha Lifeng; (6 pag.)CN110590576; (2019); A;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem