Category: ethers-buliding-blocks

Related Products of 41365-75-7,Some common heterocyclic compound, 41365-75-7, name is 1-Amino-3,3-diethoxypropane, molecular formula is C7H17NO2, 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.

Into a 25-mL round-bottom flask purged and maintained with an inert atmosphere of nitrogen, methyl (2S)-5-amino-6-bromo-2-methyl-1,2,3,4-tetrahydroquinoline-1-carboxylate (300 mg, 1.00mmol, Intermediate 1) was dissolved in toluene (5 mL). Then 3,3- diethoxypropan-1-amine (885 mg, 6.01mmol), 3rd Generation BrettPhos precatalyst (91 mg, 0.10mmol), BrettPhos (108 mg, 0.20mmol) and sodium tert-butoxide (289 mg, 3.01mmol) were added successively. The resulting solution was stirred for 2 h at 110oC under nitrogen atmosphere. The reaction mixture was cooled and the resulting solids were filtered out. The filtrate was concentrated under vacuum. The residue was subjected to purification by FCC eluting with ethyl acetate/petroleum ether (2:1). This afforded the title compound (240 mg, 62%) as a yellow oil. MS: (ES, m/z): 366 [M+H]+.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1-Amino-3,3-diethoxypropane, its application will become more common.

Reference:
Patent; FORMA THERAPEUTICS, INC.; SCHILLER, Shawn E.R.; HERBERTZ, Torsten; LI, Hongbin; GRAVES, Bradford; MISCHKE, Steven; WEST, Angela V.; ERICSSON, Anna; DOWNING, Jennifer R.; (484 pag.)WO2019/55877; (2019); A1;,
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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. 93919-56-3, name is (4-(Trifluoromethoxy)phenyl)methanamine belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. COA of Formula: C8H8F3NO

General procedure: 5.3g (0.02 mol) of methyl N-nitro-1,3-dioxoisoindoline-2-carbimidothioate (3) was dissolved in 120 mL of acetonitrile, and cooled to 0-5, dropped in a quantity of 0.02 mmol of (aryl)methanamine over 5 mins. The reaction was stirred at 0-5 for one hour again. The mixture was filtered, concentrated in vacuo and recrystallised in EtOAc – petroleum ether (1:1) to give pure products 4a~4f.

The synthetic route of 93919-56-3 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Wu, Qinglai; Zhao, Fenghai; Zhu, Xiang; Zhou, Ziyuan; Yang, Dongyan; Xu, Zhihong; Li, Junkai; Qin, Zhaohai; Natural Product Research; (2019);,
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Related Products of 929-75-9, A common heterocyclic compound, 929-75-9, name is 1,11-Diamino-3,6,9-trioxaundecane, molecular formula is C8H20N2O3, 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 for the preparation of compounds 10-15 (B) (0016) The appropriate diamines were added to compound 1a and Na2CO3 (2eq.) with stirring in DMF (5mL). The mixture was stirred overnight at room temperature. After completion, as judged by TLC, the solvent was evaporated under reduced pressure. The mixture was resolved in EtOAc and washed twice with water and brine. The organic layer was dried over Na2SO4, then filtered and concentrated. The crude product was purified by column chromatography (CH2Cl2/MeOH, 25/1 v/v) to give the target compound as a white solid.

The synthetic route of 929-75-9 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Yu, Fei; Peng, Yiyun; Wang, Qi; Shi, Yongying; Si, Longlong; Wang, Han; Zheng, Yongxiang; Lee, Emily; Xiao, Sulong; Yu, Maorong; Li, Yingbo; Zhang, Chuanling; Tang, Hengli; Wang, Chunguang; Zhang, Lihe; Zhou, Demin; European Journal of Medicinal Chemistry; vol. 77; (2014); p. 258 – 268;,
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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 592-55-2 as follows. Quality Control of 1-Bromo-2-ethoxyethane

To a solution of 3-(3-ethylazepan-3-yl)phenol (step a, 0.42 g, 1.92 mmol) in ACN (20 mL), N-ethyldiisipropylamine (0.67 mL, 3.830 mmcl) and 1-bromo-2-ethoxyethane (0.24 mL, 2.11 mmol) were added and the reaction mixture was heated at 65?C overnight. The reaction mixture was cooled and partitioned between 5% aqueous KHCO3 solution and AcOEt. The layers were separated and the organic layer wasdried over anh Na2SO4, filtered and concentrated to dryness. The crude product thus obtained was purified by flash chromatography on silica gel, gradient DCM/MeOH (0 to 10% MeOH) to give the title compound (0.15 g, 28% yield).HPLC-MS (Method A): Ret, 2.12 min; ESI-MS m/z, 292.4 (M+H).

According to the analysis of related databases, 592-55-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; LABORATORIOS DEL DR. ESTEVE, S.A.; MERCE-VIDAL, Ramon; ALMANSA-ROSALES, Carmen; GARCIA-LOPEZ, Monica; (148 pag.)WO2017/121645; (2017); A1;,
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Electric Literature of 41365-75-7,Some common heterocyclic compound, 41365-75-7, name is 1-Amino-3,3-diethoxypropane, molecular formula is C7H17NO2, 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 0.6 mmol of quinomethane 1a-1c and 0.6 mmol of 3,3-diethoxypropan-1-amine (2) or 4,4-diethoxybutan-1-amine (3) in 1 mL of 1,4-dioxane was stirred for 2-3 h at room temperature under argon. When the reaction was complete, the solvent was removed under reduced pressure (water-jet pump), and the residue was washed with hexane and dried in a vacuum (oil pump) until constant weight.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1-Amino-3,3-diethoxypropane, its application will become more common.

Reference:
Article; Vagapova; Amirova; Burilov; Pudovik; Sinyashin; Russian Journal of Organic Chemistry; vol. 51; 9; (2015); p. 1268 – 1271; Zh. Org. Khim.; vol. 51; 9; (2015); p. 1294 – 1297,4;,
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Reference of 494-99-5, 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. 494-99-5, name is 1,2-Dimethoxy-4-methylbenzene belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

(a) 80.0 g (0.6 mole) of aluminium chloride are introduced in portions, while stirring, into a solution of 84.1 g (0.5 mole) of 1,2-dimethoxy-4-methylbenzene (homopyrocatechol dimethyl ether or 4-methylveratrole) in 750 ml of 1,2-dichloroethane, during which the temperature is maintained at 20 maximum by cooling with an ice bath. Then, at 15-20, 85.0 g (approximately 73 ml, 0.55 mole) of phenyl acetyl chloride are added dropwise in the course of one hour, during which there is moderate evolution of hydrogen chloride and the aluminium chloride is dissolved. The reaction mixture is then stirred at room temperature for a further 6 hours and subsequently poured into 3000 ml of a mixture of ice and water. The resulting layers are separated and the organic phase is washed in succession with 2N hydrochloric acid, twice with water, then with 1N sodium bicarbonate solution and a further twice with water, dried, filtered and concentrated by evaporation. The partially crystallized residue is caused to crystallise completely from ether/petroleum ether (boiling range 40-65), 1-(4,5-dimethoxy-2-methylphenyl)-2-phenyl-1-ethanone having a melting point of 45-48 being obtained.

The synthetic route of 1,2-Dimethoxy-4-methylbenzene has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Ciba-Geigy Corporation; US4500542; (1985); A;,
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These common heterocyclic compound, 33311-29-4, name is 4-(2-Methoxyethoxy)aniline, 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-(2-Methoxyethoxy)aniline

To a solution of compound 3 (400 mg, 1.0 mmol) and 4-(2-methoxyethoxy)aniline (0.2 g, 1.2 mmol) in 8 ml dioxane was added 4-methylbenzenesulfonic acid monohydrate (0.15g, 0.8 mmol). The mixture was stirred at 100 0C for two hours. The solvent was evaporated. The residue was dissolved in 30 ml ethyl acetate and washed with NaHCO3 aqueous solution, water and brine. The organic layer was separated and dried over Na2SO4. After removal of solvent, the crude product was subject to chromatography on silica gel (hexane:EtOAc = 1 :1). 0.40 g of the title compound 5 was obtained: MS m/z: 530.1, 532.1(M+H+).

The synthetic route of 4-(2-Methoxyethoxy)aniline has been constantly updated, and we look forward to future research findings.

Reference:
Patent; AVILA THERAPEUTICS AND USES THEREOF; WO2009/158571; (2009); A1;,
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Synthetic Route of 1462-37-9,Some common heterocyclic compound, 1462-37-9, name is ((2-Bromoethoxy)methyl)benzene, molecular formula is C9H11BrO, 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.

Preparation 83-Amino-6-(2-benzyloxy-ethoxy)-indazole-1-carboxylic acid tert-butyl esterScheme 1, Step Hb)A mixture of 3-amino-6-hydroxy-indazole-1-carboxylic acid tert-butyl ester (249 mg, 1 mmol), K2CO3 (152 mg, 1.1 mmol) and benzyl 2-bromoethyl ether (0.179 ml, 1.1 mmol) in dry DMF (5 ml) was stirred at 50°C for 12h. More benzyl 2-bromoethyl ether (30 muIota) was added and the mixture stirred at 50°C for additional 4h. The reaction mixture was poured into water (50 ml) and extracted with EtOAc (50 ml). The organic layer wad dried over sodium sulfate and evaporated to dryness. The crude residue was purified by flash chromatography over silica gel eluting with DCM / EtOAc 7:3 affording 274 mg (yield: 72percent) of the title compound.1H-NMR (400 MHz), delta (ppm, DMSO-cie): 7.71 (d, J=8.66 Hz, 1 H), 7.48 (bs, 1 H), 7.38 – 7.27 (m, 5H), 6.91 (dd, J=2.19, 8.66 Hz, 1 H), 6.19 (bs, 2H), 4.59 (s, 2H), 4.25 – 4.20 (m, 2H), 3.85 – 3.80 (m, 2H), 1.58 (s, 9H) ESI (+) MS m/z 384 (MH+)

The synthetic route of 1462-37-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NERVIANO MEDICAL SCIENCES S.R.L.; LOMBARDI BORGIA, Andrea; CIOMEI, Marina; DONATI, Daniele; NESI, Marcella; WO2012/152763; (2012); A1;,
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Application of 1579-40-4, These common heterocyclic compound, 1579-40-4, name is Di-p-tolyl Ether, 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.

Representative Experimental Protocol: 2,7-Dimethyl-9-(4-nitro)phenyl xanthen-9-ol (R = NO2: 3e): Di-p-tolyl ether (1, 5 g, 25.5 mmol), 4-nitro benzoic acid (5.13 g, 30.7 mmol) and ZnCl2 (10 g, 73.4 mmol) are taken into a 100 ml double neck RB flask and charged with POCl3 (7.5 mL) and heated to 95 C for 4 h. The reaction mixture turned into a brown viscous mass that was difficult to stir. The reaction mixture was then cooled to room temperature and crushed ice was added slowly while keeping the low temperature. To the above mixture was added H2O (75 mL) and stirred for 12 h. The above reaction mixture was filtered and the residue was washed with H2O (20 mL) and hexane (20 mL) to afford 4-nitro-DMPx 3e as white powder. The crude product was dissolved in EtOAc and washed with NaHCO3 to remove the excess of 4-nitro benzoic acid. The EtOAc layer was evaporated under reduced pressure to furnish the desired product as fine powder 7.5 g (86%).

The synthetic route of 1579-40-4 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Banerjee, Shyamapada; Srishylam; Rajendra Prasad; Migawa, Michael T.; Swayze, Eric E.; Sanghvi, Yogesh S.; Tetrahedron Letters; vol. 53; 35; (2012); p. 4669 – 4672;,
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Application of 3616-56-6,Some common heterocyclic compound, 3616-56-6, name is 2,2-Diethoxy-N,N-dimethylethanamine, molecular formula is C8H19NO2, 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.

Under a nitrogen atmosphere, 14.1 g (0.061 mol) of the intermediate A, 11.4 g (0.071 mol) ofN,N’-dimethylaminoacetaldehyde diethyl acetal, and 110.0 g of acetic acid were stirred for 8 hours while being heated at 118°C to reflux. After the reaction solution was cooled to room temperature, the precipitated crystal was collected by filtration and washed with acetic acid (30 ml) . The resultant crystal was subjected to purification by reslurrying to afford 10.4 g (67percent yield) of IC-2 as a white crystal.

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

Reference:
Patent; Nippon Steel Chemical Co., Ltd.; EP2415772; (2012); A1;,
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