110-70-3 | Page 7 of 27 | Chiral nitrogen ligands

Extended knowledge of 110-70-3

110-70-3, 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.,110-70-3 ,N1,N2-Dimethylethane-1,2-diamine, other downstream synthetic routes, hurry up and to see

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.110-70-3, N1,N2-Dimethylethane-1,2-diamine it is a common compound, a new synthetic route is introduced below.110-70-3

A 100-mL single-neck round-bottomed flask equipped with a magnetic stirrer was purged with nitrogen, charged with N1,N2-dimethylethane-l,2-diamine (Ii) (1.61 g, 18.2 mmol), ethanol (5 mL) and Ih (500 mg, 1.82 mmol), and the reaction was stirred at room temperature for 1 h. After this time, the reaction mixture was evaporated under reduced pressure, and the resulting residue was purified by flash column chromatography to afford an 89% yield (404 mg) of Ij as a yellow oil: 1H NMR (500 MHz, DMSO-J6) 5 8.18 (d, 2H, J= 8.5 Hz), 7.60 (d, 2H, J= 8.5 Hz), 3.87 (s, IH), 3.61 (td, IH, J = 12.0, 4.0 Hz), 3.26 (ddd, IH, J = 12.0, 4.0, 2.5 Hz), 3.02 (ddd, IH, J= 12.0, 4.0, 2.5 Hz), 2.84 (s, 3H), 2.64 (td, IH, J= 12.0, 4.0 Hz), 2.06 (s, 3H).

Reference£º
Patent; CGI PHARMACEUTICALS, INC.; GENENTECH, INC.; WO2009/137596; (2009); A1;,
Chiral nitrogen ligands in late transition metal-catalysed asymmetric synthesis¡ªI. Addressing the problem of ligand lability in rhodium-catalysed hydrosilations
Nitrogen-Containing Ligands for Asymmetric Homogeneous and Heterogeneous Catalysis

A new synthetic route of N1,N2-Dimethylethane-1,2-diamine

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 N1,N2-Dimethylethane-1,2-diamine reaction routes.

110-70-3, A common heterocyclic compound, 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.”110-70-3

The ligand 345BPMEN was synthesized by modifying thepreviously reported procedure (Singh et al. 2017). To a solutionof 2-chloromethyl-4-methoxy-3,5-dimethylpyridinehydrochloride 2.032 g (9.15 mmol) in 10 mL of water, asolution of potassium carbonate (2.55 g, (18.45 mmol) inwater (10 mL) was added dropwise. After potassium carbonateaddition, very thick white ppts were formed and solutionsolidified. Additional amount of water (50 mL) was addedinto the mixture. After water addition, the reaction mixturewas stirred at room temperature for next 30 min followed bysolvent extraction with dichloromethane (3 ¡Á 20 mL). Thecombined dichloromethane layer was treated with anhydroussodium sulfate. The solution was filtered, and the solventwas removed by rotatory evaporation. The collected light brown oil was dissolved in dichloromethane (10 mL).The above solution was added dropwise to a solution ofN,N?-dimethylethylenediamine 0.493 mL (4.58 mmol) indichloromethane (15 mL). Aqueous solution of 1 M sodiumhydroxide (10 mL) was slowly added and solution wasstirred for additional 60 h at room temperature. After 60 hof stirring was the rapid addition of a second fraction ofaqueous 1 M sodium hydroxide (10 mL, 10 mmol), the productwas extracted with dichloromethane (3 ¡Á 25 mL). Thecombined organic layers were dried over anhydrous sodiumsulfate and filtered. Subsequently, the excess solvent wasevaporated by vacuum to afford brown color viscous oil(1.71 g, Yield 97%). 1H NMR (500 MHz, Methanol-d4) delta8.08 (s, 2H, pyridine ring), 3.76 (s, 6H, -O-CH3-Py), 3.57(s, 4H, -CH2-CH2-Py), 2.56 (s, 4H, -CH2-CH2-), 2.28 (d,6H, CH3-Py), 2.24 (d, 6H, CH3-Py), 2.16 (s, 6H, -N-CH3).ESI-MS+: [345BPMEN + H]+ = 387.32 m/z+ (experimental)387.27 m/z+ (theoretical).

Reference£º
Article; Botcha, Niharika Krishna; Gutha, Rithvik R.; Sadeghi, Seyed M.; Mukherjee, Anusree; Photosynthesis Research; vol. 143; 2; (2020); p. 143 – 153;,
Chiral nitrogen ligands in late transition metal-catalysed asymmetric synthesis¡ªI. Addressing the problem of ligand lability in rhodium-catalysed hydrosilations
Nitrogen-Containing Ligands for Asymmetric Homogeneous and Heterogeneous Catalysis

Sources of common compounds: 110-70-3

110-70-3, 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. N1,N2-Dimethylethane-1,2-diamine, cas is 110-70-3,the chiral-nitrogen-ligands compound, it is a common compound, a new synthetic route is introduced below.

Example 1203 ,3 -Dimethyl-2-{3 – [methyl- (2-methylamino-ethyl) -amino] -phenyl}- 1 ,2,3 ,4- tetrahydro-quinoline-6-carboxylic acidA mixture of 2-(3-bromo-phenyl)-3,3-dimethyl-l,2,3,4-tetrahydro-quinoline-6-carboxylic acid (600 mg, 1.7 mmol), N,N’-dimethyl-ethane-l,2-diamine (0.37 mL, 3.4 mmol), copper(I) iodide (96 mg, 0.5 mmol), N, N-dimethylglycine hydrochloride (140 mg, 1.0 mmol) and potassium carbonate (923 mg, 6.7 mmol) in dimethyl sulfoxide (5 mL)was stirred at 120C for 16 h. Then the reaction mixture cooled to room temperature. The reaction mixture was extracted with ethyl acetate (2 x 150 mL), washed with water (2 x 50 mL) and saturated aqueous ammonium chloride solution (2 x 50 mL), dried over anhydrous sodium sulfate and then concentrated in vacuo. Purification by Waters automated flash system (column: Xterra 30 mm x 100 mm, sample manager 2767, pump 2525, detector: ZQ mass and UV 2487, solvent system: acetonitrile and 0.1% ammonium hydroxide in water) afforded 3,3-dimethyl-2-{3- [methyl-(2-methylamino-ethyl)-amino] – phenyl} -l,2,3,4-tetrahydro-quinoline-6-carboxylic acid (500 mg, 80%) as a white solid : LC/MS m/e calcd for C22H29N3O2 (M+H)+: 368.50, observed: 368.1.

Reference£º
Patent; F. HOFFMANN-LA ROCHE AG; CHEN, Li; FENG, Lichun; HUANG, Mengwei; LIU, Yongfu; WU, Guolong; WU, Jim, Zhen; ZHOU, Mingwei; WO2011/128251; (2011); A1;,
Chiral nitrogen ligands in late transition metal-catalysed asymmetric synthesis¡ªI. Addressing the problem of ligand lability in rhodium-catalysed hydrosilations
Nitrogen-Containing Ligands for Asymmetric Homogeneous and Heterogeneous Catalysis

Discovery of N1,N2-Dimethylethane-1,2-diamine

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 N1,N2-Dimethylethane-1,2-diamine, 110-70-3

Add in a 100mL single-mouth bottleN1,N2-dimethylethyl-1,2-diamine (4g, 45mmol), cooled to about 0 C in an ice bath,Then (Boc) 2O (5 g, 23 mmol) in DCM (20 mL)The temperature was raised to 25 C and the reaction was stirred for 4 h.Concentrated under reduced pressure, a saturated sodium carbonate solution was added to the residue, and extracted three times with ethyl acetate (30 mL¡Á3).The organic phase was combined, washed three times with saturated brine (20 mL¡Á3) and dried over anhydrous sodiumThe mixture was suction filtered under reduced pressure, and the filtrate was evaporated.The crude product was purified by column chromatography eluting with EtOAc EtOAcConcentration under reduced pressure gave 2.1 g of a yellow oil.

Reference£º
Patent; Beijing Purunao Bio-technology Co., Ltd.; Zhang Peilong; Shi Hepeng; Lan Wenli; Song Zhitao; (250 pag.)CN108707139; (2018); A;,
Chiral nitrogen ligands in late transition metal-catalysed asymmetric synthesis¡ªI. Addressing the problem of ligand lability in rhodium-catalysed hydrosilations
Nitrogen-Containing Ligands for Asymmetric Homogeneous and Heterogeneous Catalysis

Extended knowledge of 110-70-3

Step. A: N-Methyl-N’-methyl-N’-t-butoxycarbonylethylenediamine A solution of 1 gram (4.58 mmole) of di-t-butyl-dicarbonate in 8 mL of CH2 Cl2 at 0 C. was treated with 0.98 mL (9.16 mmole) of N-methyl-N’-methylethylenediamine. After 20 min the cooling bath was removed and the mixture allowed to warm to 22 C. After 4 hours the mixture was concentrated in vacuo. The residue was purified by flash chromatography on 68 g silica gel eluding with 1 liter of 100:9:0.3 CH2 Cl2:MeOH: ammonia water, then 500 mL of 100:11:0.3 CH2 Cl2:MeOH: ammonia water to give 190 mg (22%) of a volatile oil.

Reference£º
Patent; Merck & Co., Inc.; US5344830; (1994); A;,
Chiral nitrogen ligands in late transition metal-catalysed asymmetric synthesis¡ªI. Addressing the problem of ligand lability in rhodium-catalysed hydrosilations
Nitrogen-Containing Ligands for Asymmetric Homogeneous and Heterogeneous Catalysis

The important role of N1,N2-Dimethylethane-1,2-diamine

110-70-3, The major producers of chemicals have been the Europe, Japan and China. Due to the growing call for a cleaner, greener environment, people will have to find innovative ways to maintain their relevance. N1,N2-Dimethylethane-1,2-diamine, cas is 110-70-3,the chiral-nitrogen-ligands compound. Here is a downstream synthesis route of the compound.

2-(2-methoxyphenyl)-1,3-dimethylimidazolidine. A solution of o-anisaldehyde (9.0 g, 66 mmol) and N,N’-dimethylethylenediamine (7.9 mL, 73 mmol) in ethanol (180 mL) was stirred at r.t. for overnight. MgSO4 (30 g) was added and the mixture was stirred for 20 min. The reaction mixture was filtered and washed with ether. The solvent was removed in vacuo to afford 2-(2-methoxyphenyl)-1,3-dimethylimidazolidine as a light yellow solid, 12 g, yield 88%. 1H NMR (500 MHz, CHLOROFORM-D) delta ppm 2.21 (s, 6H) 2.57-2.72 (m, 2H) 3.34 (d, J=2.75 Hz, 2H) 3.82 (s, 3H) 4.13 (s, 1H) 6.88 (d, J=8.24 Hz, 1H) 7.00 (t, J=7.48 Hz, 1H) 7.25-7.30 (m, 1H) 7.67 (d, J=7.63 Hz, 1H).

Reference£º
Patent; Bristol-Myers Squibb Company; US2007/270406; (2007); A1;,
Chiral nitrogen ligands in late transition metal-catalysed asymmetric synthesis¡ªI. Addressing the problem of ligand lability in rhodium-catalysed hydrosilations
Nitrogen-Containing Ligands for Asymmetric Homogeneous and Heterogeneous Catalysis

Introduction of a new synthetic route about 110-70-3

The major producers of chemicals have been the Europe, Japan and China. Due to the growing call for a cleaner, greener environment, people will have to find innovative ways to maintain their relevance. N1,N2-Dimethylethane-1,2-diamine, cas is 110-70-3,the chiral-nitrogen-ligands compound. Here is a downstream synthesis route of the compound., 110-70-3

To a solution of compound 9-3 (10 g, 36.5 mmol) in EtOH was added dropwise compound 9-3-1 (39 mL, 365 mmol) under nitrogen atmosphere at 0 C., and then the reaction solution was stirred at 20 C. for 2 h, followed by concentration. The residue was purified by column chromatography to give the title compound 9-4 (yellow solid, 5.5 g, Yield 56%). 1H NMR (400 MHz, CDCl3): delta ppm 8.16 (d, J=8.8 Hz, 2H), 7.59 (d, J=8.8 Hz, 2H), 3.80 (s, 1H), 3.60-3.80 (m, 1H), 3.15-3.30 (m, 1H), 3.00-3.10 (m, 1H), 2.93 (s, 3H), 2.60-2.75 (m, 1H), 2.15 (s, 3H).

Reference£º
Patent; Hubei Bio-Pharmaceutical Industrial Technological Institute Inc.; Humanwell Healthcare (Group) Co., Ltd.; Wang, Xuehai; Wu, Chengde; Xu, Yong; Shen, Chunli; Li, Li’e; Hu, Guoping; Yue, Yang; Li, Jian; Guo, Diliang; Shi, Nengyang; Huang, Lu; Chen, Shuhui; Tu, Ronghua; Yang, Zhongwen; Zhang, Xuwen; Xiao, Qiang; Tian, Hua; Yu, Yanping; Chen, Hailiang; Sun, Wenjie; He, Zhenyu; Shen, Jie; Yang, Jing; Tang, Jing; Zhou, Wen; Yu, Jing; Zhang, Yi; Liu, Quan; (251 pag.)US2017/313683; (2017); A1;,
Chiral nitrogen ligands in late transition metal-catalysed asymmetric synthesis¡ªI. Addressing the problem of ligand lability in rhodium-catalysed hydrosilations
Nitrogen-Containing Ligands for Asymmetric Homogeneous and Heterogeneous Catalysis

Extracurricular laboratory: Synthetic route of 110-70-3

36.2 g (0.40 mol) acrylic acid chloride and 16 mg MEHQ were dissolved in 600 ml methylene chloride in a 1.5-l sulphonation flask and cooled to -5 C. Then, a mixture of 17.6 g (0.20 mol) N,N’-dimethylethylenediamine, 40.8 g (0.40 mol) triethylamine and 400 ml methylene chloride was added dropwise accompanied by stirring so that the temperature remained between -5 and 0 C. After 1.5 h stirring, the mixture was allowed to warm up to room temperature, stirred overnight, the precipitate formed was filtered off and the filtrate concentrated under vacuum. The raw product was taken up in 150 ml acetone, filtered through a frit with 50 g silica gel 60 and concentrated again. After repeating this process, 30.1 g (77% yield) of a light yellow liquid remained. 1H-NMR (400 MHz, CDCl3): delta=3.10 and 3.14 (s; 2*3H, CH3), 3.54-3.67 (2m; 4H, CH2N), 5.68, 6.35 and 6.56 (m; 3*2H, CH=CH2) ppm.

Reference£º
Patent; Ivoclar Vivadent AG; US6953832; (2005); B2;,
Chiral nitrogen ligands in late transition metal-catalysed asymmetric synthesis¡ªI. Addressing the problem of ligand lability in rhodium-catalysed hydrosilations
Nitrogen-Containing Ligands for Asymmetric Homogeneous and Heterogeneous Catalysis

Some scientific research about 110-70-3

Synthesis of [N,N?-Dimethyl-N,N?-bis-(pyridine-2-ylmethyl)-1,2-diaminoethane] was taken from a previously reported procedure [16]. 2-(chloromethyl)pyridine hydrochloride (1.501 g, 9.15 mmol) dissolved in 5 mL deionized (DI) water was added dropwise to an aqueous solution containing K2CO3 (2.556 g, 18.49 mmol) dissolved in 7.5 mL DI water. The resulting mixture was stirred for 30 min. The mixture was extracted with CH2Cl2 (3¡Á10 mL). The organic phase was collected and dried with anhydrous Na2SO4. The dried solution was concentrated in vacuo to afford orange oil. A solution containing N,N?-dimethylethylenediamine (0.471 mL, 4.38 mmol) in 15 mL CH2Cl2 was added dropwise to the aforementioned orange oil dissolved in 5 mL CH2Cl2. An aqueous solution containing NaOH (0.311 g, 7.78 mmol) dissolved in 7.6 mL DI water was slowly added to organic mixture and stirred at room temperature. After 60 h, a second portion of NaOH solution(0.318 g, 7.95 mmol) was quickly added to the mixture. The combined mixture was extracted with CH2Cl2 (3¡Á20 mL) and dried with anhydrous Na2SO4. The organic solution was concentrated in vacuo to afford a brown oil, BPMEN (Yield: 0.631 g, 2.33 mmol, 70%) 1H NMR(500 MHz, CD2Cl2) delta 8.46 (dt, 2H, pyridine ring), 7.80 (m, 2H, pyridinering), 7.51 (m, 2H, pyridine ring), 7.30 (m, 2H, pyridine ring), 3.70 (m,4H, -CH2), 2.66 (m, 4H, -CH2), 2.27 (s, 6H, -CH3). ESI-MS (MeOH).Observed m/z 271.25 [BPMEN+H+] (z=1); simulated m/z 271.19.

Reference£º
Article; Pella, Bruce J.; Niklas, Jens; Poluektov, Oleg G.; Mukherjee, Anusree; Inorganica Chimica Acta; vol. 483; (2018); p. 71 – 78;,
Chiral nitrogen ligands in late transition metal-catalysed asymmetric synthesis¡ªI. Addressing the problem of ligand lability in rhodium-catalysed hydrosilations
Nitrogen-Containing Ligands for Asymmetric Homogeneous and Heterogeneous Catalysis

A new synthetic route of N1,N2-Dimethylethane-1,2-diamine

110-70-3, 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.110-70-3, N1,N2-Dimethylethane-1,2-diamine it is a common compound, a new synthetic route is introduced below.

2, phosphorus trichloride (27.5g, 0.2mol) and triethylamine (40.5g, 0.4mol) was dissolved in 200mL n-hexane, the solution was placed in an ice water bath cooled to 0-5 C;N,N-dimethylethylenediamine (17.6 g, 0.2 mol) was slowly added dropwise to the solution under stirring.Hexane solution; after the addition is complete, the ice water bath is removed, and the temperature is naturally raised to room temperature, continue to react 4h; reaction is over, filter, collect the filtrate, after testing,Which contains the product of formula (III) wherein both R groups in formula (III) are methyl;

Reference£º
Patent; Wanhua Chemical Group Co., Ltd.; Lv Yingdong; Zhu Longlong; Liu Junxian; Song Mingyan; Xue Yongyong; Li Jinming; Zhang Tao; Li Yuan; (10 pag.)CN107915758; (2018); A;,
Chiral nitrogen ligands in late transition metal-catalysed asymmetric synthesis¡ªI. Addressing the problem of ligand lability in rhodium-catalysed hydrosilations
Nitrogen-Containing Ligands for Asymmetric Homogeneous and Heterogeneous Catalysis