Month: May 2021

Some common heterocyclic compound, 120758-03-4, name is 2-Chloro-3,5-dimethoxyaniline, molecular formula is C8H10ClNO2, 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: C8H10ClNO2

Step 4: Synthesis of Intermediate 5 [00522j Into a sealed vessel was added Intermediate 4 (1.50 g, 8.00 mmol) in DMA (5 mL, 53.3 mmol), followed by DIPEA (820 tl, 8.80 mmol). The reaction mixture was allowed to stir for 10 mm. at ambient temperature, and 2,4-dichloro-5-(iodomethyl)pyrimidine from Example 1 (2.31 g, 8.00 mmol) was added. The reaction mixture was allowed to stir at 60 C for 7.5 h, then 16 h at ambient temperature. The reaction mixture was concentrated and azeotroped several times with toluene. EtOAc was added and the organic layer washed with brine (3 x). The organic layers were dried with sodium sulfate, concentrated and purified by flash column chromatography (eluting with 5-25% EtOAc in heptane) to give 1.75 g of the title compound MS mlz: 348.2 (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 120758-03-4, its application will become more common.

Reference:
Patent; CELGENE AVILOMICS RESEARCH, INC.; SANOFI; D’AGOSTINO, Laura Akullian; SJIN, Robert Tjin Tham; NIU, Deqiang; MCDONALD, Joseph John; ZHU, Zhendong; LIU, Haibo; MAZDIYASNI, Hormoz; PETTER, Russell C.; SINGH, Juswinder; BARRAGUE, Matthieu; GROSS, Alexandre; MUNSON, Mark; HARVEY, Darren; SCHOLTE, Andrew; MANIAR, Sachin; WO2014/144737; (2014); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Related Products of 909122-17-4, 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. 909122-17-4, name is 1-Bromo-2-chloro-4-ethoxy-3-fluorobenzene belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

First Step 2.6 g of well dried magnesium and 20 mL of THF were added to a reactor in a nitrogen atmosphere and heated to 40° C. 26.6 g of the compound (C12) dissolved in 80 mL of THF was added dropwise thereto slowly in a temperature range of 30 to 45° C., followed by stirring for 20 minutes. Thereafter, 21.2 g of a compound (b45) dissolved in 20 mL of THF was added dropwise thereto slowly in a temperature range of 30 to 35° C., followed by stirring for 60 minutes. The resulting reaction mixture was cooled to 25° C. and then poured into 100 mL of 3N hydrochloric acid and 100 mL of toluene, followed by mixing. The mixture was then left to rest to separate into an organic layer and an aqueous layer, followed by extracting to the organic layer. The resulting organic layer was collected and washed with water, a 2N sodium hydroxide aqueous solution, a saturated sodium hydrogen carbonate aqueous solution and water, followed by drying over anhydrous magnesium sulfate. Thereafter, the solvent was distilled off under reduced pressure to obtain 47.0 g of 4-(2-chloro-4-ethoxy-3-fluorophenyl)-trans-4′-propyl-bicyclohexyl-4-ol (b48). The resulting compound (b48) was a yellow oily substance.

The synthetic route of 1-Bromo-2-chloro-4-ethoxy-3-fluorobenzene has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Goto, Yasuyuki; Shimada, Teru; Sugiura, Teruyo; US2006/198968; (2006); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Electric Literature of 871-90-9,Some common heterocyclic compound, 871-90-9, name is 8-Chlorooct-1-ene, molecular formula is C8H15Cl, 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: In the glove box, add to the 8mL vial(R,R,R,R)-ANIPE-CuCl Compound 35 (3.4 mg, 4 mmol,2.0mol%),tBuONa (33.6 mg, 0.3 mmol, 1.5 equiv) and n-hexane (1.0 mL), and the reaction mixture was reacted at room temperature for 1 hour.B2dmpd2 (113 mg, 0.4 mmol, 2.0 equiv) was added, and the reaction mixture was further reacted at room temperature for 30 minutes.Add non-activated terminal olefin compound 36 (0.2 mmol) and MeOH (16 uL, 0.4 mmol, 2.0 equiv), the reaction mixture was reacted at room temperature for 24 hours.The mixture was filtered through Celite, diluted with ethyl acetate.The reaction solution was sparged and the silica gel was passed through a column to give a chiral alkyl boron compound 37a.The enantioselectivity of the chiral alkyl boride is determined by oxidation of H2O2/NaOH to give the chiral alcohol.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 8-Chlorooct-1-ene, its application will become more common.

Reference:
Patent; Chinese Academy Of Sciences Shanghai Organic Chemistry Institute; Shi Shiliang; Cai Yuan; Yang Xintuo; Li Feng; (67 pag.)CN109776422; (2019); A;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Related Products of 54730-35-7, 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. 54730-35-7, name is 3,5-Dichloro-4-methylaniline, This compound has unique chemical properties. The synthetic route is as follows.

Preparation 9; 5-bromo-l,3-dichloro-2-methylbenzene; Suspend 3, 5 -dichloro-4-methylaniline in 48% HBr (5 mL) and water (5 mL) and heat with a heat gun until the mixture is near the boiling point. Cool the slurry to room temperature and then cool to 00C with an ice/brine bath. Add dropwise a solution of sodium nitrite (109 mg, 1.58 mmol) in water (2 mL). After the addition is complete, stir the reaction an additional 15 min in the cold bath. Add a solution of CuBr (1.08 g, 7.53 mmol) in 48% HBr (2 mL) and heat the rapidly stirring reaction to 500C for 1 hour. Cool the reaction to room temperature, dilute with EtOAc and discard the aqueous layer. Wash the organic layer with water and brine, dry with MgSO4, filter through celite and concentrate to an orange residue. Purify the residue by silica gel chromatography eluting with hexanes to afford 164 mg (45%) of the product as a yellow solid.

The chemical industry reduces the impact on the environment during synthesis 3,5-Dichloro-4-methylaniline. I believe this compound will play a more active role in future production and life.

Reference:
Patent; ELI LILLY AND COMPANY; WALLACE, Owen, Brendan; WO2007/127726; (2007); A2;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Electric Literature of 90390-33-3, 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. 90390-33-3, name is 3-Chloro-5-fluorobenzylamine, This compound has unique chemical properties. The synthetic route is as follows.

Triethylamine (0.74 ml) and propanephosphoric anhydride (T3P; 1.02 g) are added at 0 C. to a solution of 2-oxo-1-phenylazepane-3-carboxylic acid (250 mg) and 3-chloro-5-fluorobenzylamine (205 mg) in dichloromethane (15 ml). When the reaction has been brought to completion at RT, the mixture is diluted with further dichloromethane and washed with 10% sodium bicarbonate solution and saturated NaCl solution. The organic phase is treated in the usual manner, and the residue is purified, giving the product as colourless solid in a yield of 87% (350 mg); 10430] LCMS: mass found (M+1,375.2)10431] MethodA: 0.1%ofTFAinH2O, B: 0.1%ofTFAin ACN: flow-2.0 ml/min.10432] Column: X Bridge C8 (50×4.6 mm, 3.5 tm)+ve mode10433] Rt (mm): 4.57 area % 98.66 (max), 97.22 (220 nm) 10434] HPLC:10435] MethodA: 0.1% of TFA in H20, B: 0.1% of TFA inACN, flow rate: 2.0 ml/min10436] Column: XBridge C8 (50×4.6) mm, 3.5 tm10437] Rt (mm): 4.63 area % 97.55 (max), 97.87 (220 nm);10438] ?H NMR (400 MHz, DMSO-d5): oe [ppm]8.37-8.36(m, 1H), 7.40-7.36 (m, 2H), 7.27-7.20 (m, 6H), 4.44-4.38 (m,1H), 4.25-4.20 (m, 1H), 3.92-3.83 (m, 2H), 3.60-3.59 (m,1H), 2.03-2.01 (m, 1H), 1.98-1.95 (m, 1H), 1.78-1.63 (m,4H).

The chemical industry reduces the impact on the environment during synthesis 3-Chloro-5-fluorobenzylamine. I believe this compound will play a more active role in future production and life.

Reference:
Patent; MERCK PATENT GmbH; Heinrich, Timo; Zenke, Frank; Krier, Mireille; Friese-Hamim, Manja; Seenisamy, Jeyaprakashnarayanan; US2015/31670; (2015); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Electric Literature of 928-50-7, These common heterocyclic compound, 928-50-7, name is 5-Chloropent-1-ene, 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.

1) 1-Chloropent-4-ene (0.1 mol) and Na2CO3 (11 g) in THF (100 g) are added to 3,3,3-trifluoropropan-1-ol (11 g), the mixture is stirred under reflux for 4 hrs, and the allyl ether is then isolated using conventional laboratory methods.

Statistics shows that 5-Chloropent-1-ene is playing an increasingly important role. we look forward to future research findings about 928-50-7.

Reference:
Patent; Hierse, Wolfgang; Ignatyev, Nikolai (Mykola); Seidel, Martin; Montenegro, Elvira; Kirsch, Peer; Bathe, Andreas; US2010/152081; (2010); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Application of 69411-05-8, A common heterocyclic compound, 69411-05-8, name is 3-Chloro-5-trifluoromethylaniline, molecular formula is C7H5ClF3N, 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 cold (0C) suspension of 3-chloro-5-(trifluoromethyl)aniline (1 g, 5.11 mmol, Eq: 1.00) and calcium carbonate (1.02 g, 10.2 mmol, Eq: 2) in water (11.1 ml) and dichloromethane (11.1 ml) was added thiophosgene (647 mg, 430 mu, 5.62 mmol, Eq: 1.1). The biphasic reaction mixture was allowed to warm to room temperature and was vigorously stirred for 16h. IN HC1 (10 mL) was added and the reaction mixture was pardoned between water and EtOAc. The organic layer was washed with water and brine, adsorbed unto silica (3g), and purified on silica gel (column 40 g, hexane/AcOEt 1:0 to 85: 15) to give 880 mg (72%) of the desired product as a colorless oil.

The synthetic route of 69411-05-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; PLANCHER, Jean-Marc; WEIKERT, Robert James; WO2014/135423; (2014); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

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. 621-62-5, name is 2-Chloro-1,1-diethoxyethane, This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C6H13ClO2

EXAMPLE 3 Preparation of 2-benzoyloxyacetaldehyde diethyl acetal Chloroacetaldehyde diethyl acetal (2.00 g), potassium benzoate (1.91 g), potassium bromide (0.30 g) and DMF (20 mL) were placed in a three-neck flask, followed by refluxing. Twenty hours later, the reaction mixture was cooled to room temperature, and water (30 mL) and ethyl acetate (80 mL) were added thereto, followed by stirring. After filtration, the organic layer was washed with water (30 mL) and was dried over anhydrous sodium sulfate. Subsequent filtration and vacuum concentration yielded the target compound (0.97 g) in a yield of 31%.

According to the analysis of related databases, 621-62-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Daicel Chemical Industries, Ltd.; US2005/234246; (2005); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Synthetic Route of 3260-88-6, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 3260-88-6 name is 2-Methyl-3-chloroanisole, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

3-Chloro-2-methylphenol Process Variant b2)-Second Step-Preparation of Compounds of the Formula (I-1) 3.1 g (0.02 mol) of 3-chloro-2-methylanisole are heated in 20 ml of 50% sulphuric acid for 18 hours with reflux. After cooling, the reaction mixture is extracted three times with dichloromethane, dried over sodium sulphate and concentrated to dryness under reduced pressure. 3-Chloro-2-methylphenol is obtained as a solid (2.9 g, content by HPLC: 11.7%, 12% of theory).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-Methyl-3-chloroanisole, and friends who are interested can also refer to it.

Reference:
Patent; Huebsch, Walter; Lantzsch, Reinhard; Mueh, Thorsten; Weintritt, Holger; US2003/92944; (2003); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

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. 136773-69-8, name is 4-Chloro-7-fluoropyrrolo[1,2-a]quinoxaline belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Safety of 4-Chloro-7-fluoropyrrolo[1,2-a]quinoxaline

A mixture of 7-fluoro-4-chloropyrrolo[1,2-alpha]quinoxaline 13c (100 mg, 0.45 mmol), hydrazine monohydrate (5 mL), and DMF (2 mL) was heated to 70-80 C. for 1 h. Crushed ice was then added and the mixture was extracted with EtOAc. The organic layer was separated and shaken with water and brine successively. After evaporation of the volatiles, compound 14c was obtained as a solid (84 mg, 86% yield) and used in the subsequent step without further purification. An analytical sample was obtained by crystallization; mp 158 C. (dec.) (dichloromethane/light petroleum); IR (KBr) 3300 cm-1; 1H NMR (DMSO-d6) 4.56 (bs, 2 H), 6.66 (t, 1 H, J=3.2 Hz), 7.03 (m, 2 H), 7.18 (dd, 1 H, J=10.6, 2.7 Hz), 8.02 (dd, 1 H, J=8.9, 5.6Hz), 8.15 (s, 1 H), 8.87 (bs, 1 H). Anal. Calcd for C11H9FN4: C, H, N.

The synthetic route of 136773-69-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; University of Southern California; US2006/142294; (2006); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics