Month: July 2021

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. 6276-54-6, name is 3-Chloropropan-1-amine hydrochloride belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Quality Control of 3-Chloropropan-1-amine hydrochloride

3-Chloropropylamine hydrochloride (12 mg, 0.093 mmol), 1-(3-dimethylaminopropyl)-3-ethyl-carbodiimide hydrochloride (EDC, 17 mg, 0.089 mmol), 4,4-dimethylaminopyridine (DMAP, 1 mg 0.008 mmol) and Et3N (50 muL, 0.359 mmol) were added to a solution of 1-pyreneacetic acid (20 mg, 0.077 mmol) in anhydrous CH2Cl2 (1 mL) under an argon atmosphere. The reaction mixture was stirred at room temperature for 7 h, quenched with aqueous saturated NH4Cl solution, and extracted with AcOEt. The organic layer was washed with brine, dried over Na2SO4 and evaporated in vacuo. The resulting residue was purified by silica gel column chromatography (CH2Cl2) to give 6 as a pale yellow solid (13 mg, 50%). 1H-NMR (400 MHz, CDCl3) delta (ppm) 8.20 (2H, d, J = 7.6 Hz), 8.15 (3H, d, J = 7.9 Hz), 8.08 (1H, d, J = 9.2 Hz), 8.04 (1H, d, J = 9.2 Hz), 8.02 (1H, t, J = 7.9 Hz), 7.88 (1H, d, J = 7.9 Hz), 4.28 (2H, s), 3.31 (2H, t, J = 6.4 Hz), 3.25 (2H, q, J = 6.4 Hz), 1.78 (2H, quin, J = 6.4 Hz). 13C-NMR (125 MHz, CDCl3) delta (ppm) 171.23, 131.28, 131.16, 130.76, 129.53, 128.50, 128.16, 127.69, 127.27, 126.28, 125.60, 125.48, 125.20, 125.12, 124.62, 122.76, 42.22, 42.08, 37.28, 31.86. IR (cm-1): 3293, 1646, 1544. HR ESI-MS (m/z): calcd. for [C21H19ClNO]+, 336.1150 ([M+H]+); found 336.1161.

The synthetic route of 6276-54-6 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Fuchi, Yasufumi; Obayashi, Hideto; Sasaki, Shigeki; Molecules; vol. 20; 1; (2015); p. 1078 – 1087;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Electric Literature of 363-51-9, 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 363-51-9 as follows.

EXAMPLE 7 (1H-Benzimidazol-2-yl)-(2-chloro-6-fluorophenyl)amine hydrochloride 2-Chloro-6-fluoroaniline (0.48 g) and 2-chlorobenzimidazole (0.5 g) were mixed in a flask and then kept at 170 C. for 30 min. After cooling, the residue was dissolved out of the flask at boiling heat using 1 N HCl and 10% ethanol. The material dissolved out was then stirred at RT for 30 min, then the insoluble material was filtered off with suction and the filtrate was evaporated. The residue was purified by means of preparative HPLC on RP-18 using acetonitrile/water (0.05% TFA). The clean fractions were combined, the acetonitrile was stripped off, the residue was adjusted to pH 10 with potassium carbonate solution, extracted three times with EA, and then the combined phases were dried, filtered, and concentrated. The residue was taken up using HCl/water and freeze-dried. 27 mg of the title compound were obtained. LCMS-Rt: 3.45 min; MS (ES+, M+H+): 262.0

According to the analysis of related databases, 363-51-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Hofmeister, Armin; Heinelt, Uwe; Lang, Hans-Jochen; Bleich, Markus; Wirth, Klaus; Gekle, Michael; US2002/132842; (2002); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Application of 202197-26-0, A common heterocyclic compound, 202197-26-0, name is 3-Chloro-4-((3-fluorobenzyl)oxy)aniline, molecular formula is C13H11ClFNO, 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: To a 50-ml glass round-bottom flask was added sequentially the primary amine 2 (1.0 mmol; aliphatic, aromatic or heteroaromatic; as free naked amine or as HCl, MsOH, TsOH or tartrate salt), FSO2N3 solution (containing 1.0 mmol FSO2N3, approximately 200 mM in DMF/MTBE 1:1, v/v, approximately 5 ml, volume adjusted according to the concentration; prepared according to the above procedure and diluted with equal volume of DMF) and aqueous KHCO3 solution (3.0 M, 1.33 ml, containing 4.0 mmol KHCO3). The reaction mixture was stirred for 5 min at room temperature, while monitoring by LC-MS. After completion, EtOAc (40 ml) was added and the mixture was washed sequentially with brine (60 ml × 6), water (60 ml × 2) and brine (60 ml), dried over Na2SO4, concentrated by rotary evaporation and dried under vacuum to afford the azide product 3. For products containing acidic functional groups, this extraction process was modified with acidified aqueous phase (acidified with aqueous HCl). Detailed procedures and the various modifications, as well as the characterization data for each compound, can be found in Supplementary Information 1.

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Article; Meng, Genyi; Guo, Taijie; Ma, Tiancheng; Zhang, Jiong; Shen, Yucheng; Sharpless, Karl Barry; Dong, Jiajia; Nature; vol. 574; 7776; (2019); p. 86 – 89;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

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 81927-55-1 as follows. Application In Synthesis of Benzyl 2,2,2-trichloroacetimidate

To a solution of scheme 58 compound Si (24 g, 0136 mol) and benzyl 2,2,2- thchioroaceiirnidate (5 1)3 g, 0204 inol) in cvchexanedichloromethane (600 inL120 ml..) at room temperature was added tritluorornethanesulfonic anhydride (cat. 1 .2 mE) dropwise. The reaction mixture was stirred at room temperature overnight and filtered. The filtrate was washed 4lth sat N& K (Y and hnne, dned o ci anh chous Na2SO- filteted and ctncentiated he residue was purified by column chromatography on silica gel (eluted with petroleum ether: ethyl aceiate =10: 1) to give the title compound (35 g, 933% yield) as a yellow oil.

According to the analysis of related databases, 81927-55-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ACHILLION PHARMACEUTICALS, INC.; WILES, Jason Allan; PHADKE, Avinash S.; DESHPANDE, Milind; AGARWAL, Atul; CHEN, Dawei; GADHACHANDA, Venkat Rao; HASHIMOTO, Akihiro; PAIS, Godwin; WANG, Qiuping; WANG, Xiangzhu; GREENLEE, William; (358 pag.)WO2017/35411; (2017); 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. 1205-71-6, name is 4-Chloro-N-phenylaniline belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Computed Properties of C12H10ClN

In a 250ml round bottom flask,10-bromobenzo [b] naphtho [2,1-d] furan (12 mmol), copper iodide (15 mmol), potassium tert-butoxide (65 mmol),1,2-diaminocyclohexane (12 mmol)And (4-chloro-phenyl) -phenylamine (12 mmol) were added to dry 1,4-dioxane (100 ml) and refluxed for 48 hours under N2 atmosphere. The obtained intermediate was cooled to room temperature, and added Water was then filtered through a pad of diatomaceous earth while being extracted with dichloromethane, then washed with water, and dried over anhydrous magnesium sulfate. After filtration and evaporation, the crude product was purified by silica gel column chromatography to obtain the intermediate HT002-1.

The synthetic route of 1205-71-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Shanghai Tianma Organic Shine Display Co., Ltd.; Zhang Lei; Gao Wei; Niu Jinghua; Dai Wenpeng; Xiao Wenjing; Lu Yan; Zhu Hongyan; (28 pag.)CN110746391; (2020); A;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Application of 1996-29-8,Some common heterocyclic compound, 1996-29-8, name is 1-Bromo-4-chloro-2-fluorobenzene, molecular formula is C6H3BrClF, 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, 104.7 g of 2-fluoro-4-chlorobromobenzene, 400 ml of THF and 67.3 g of potassium t-butoxide were added to a 1 L three-necked flask.After cooling to -60 C, 300 mL of n-butyl lithium solution (2 mol / L) was added dropwise, and the addition was completed -50 to -60 CAfter heat preservation for 1 h, the temperature was raised to -30 C, and then 172.6 g of tributyl borate was added dropwise.After the completion of the dropwise addition, the temperature was naturally raised to room temperature for 2 hours.The reaction solution is acidified with hydrochloric acid, extracted with petroleum ether, and washed with water.Concentrated to a white solid a-1, 75.1 g, Y = 86.1%,LC = 98.15%. 2) Synthesis of a-2: under nitrogen protection,Add a-1 41.9g to a 250ml three-necked bottle.4-bromo resorcinol37.8g, potassium carbonate 27.6g,TBAB 2.0g, Pd(0) 0.5g, ethanol 100mL, water 50mL,After stirring at reflux for 3 h, the reaction solution was acidified with dilute hydrochloric acid.Extracted with ethyl acetate and concentrated.Recrystallization from 2 times ethanol gave a white solid a-2.38.5 g, Y = 80.7%, GC = 98.78%. 3) Synthesis of a-3: under nitrogen protection,Add a-223.9g to a 100ml three-necked bottle.DMF 70mL, 60% sodium hydride 8.0g,Reflow reaction for 0.5 h,The reaction solution was poured into ice water, neutralized with dilute hydrochloric acid, and extracted with ethyl acetate, and evaporated to give a yellow solid a-3, 20.9 g,GC=98.61% 4) Synthesis of a-4: A-320.9 g was sequentially added to a 100 ml three-necked flask.60 mL of dichloromethane,21.7 g of trimethylchlorosilane, reacted at room temperature for 0.5 h, concentrated,A yellow solid a-4, 27.8 g, Y = 100%, GC = 98.65%. 5) Synthesis of a-5: under nitrogen protection,Add a-423.3g to a 250 mL three-necked flask.THF 100ml, potassium t-butoxide 10.8g, after cooling to -50 C,60 mL of n-butyllithium solution (2 mol/L) was added dropwise.After the addition is completed, the temperature is kept at -50 to -40 C for 1 h.After heating to -30 C, 27.6 g of tributyl borate was added dropwise.After the completion of the dropwise addition, the temperature was naturally raised to room temperature for 2 hours. The reaction mixture was acidified with hydrochloric acid, extracted with EtOAc EtOAc.Y = 74.2%, LC = 98.66%. 6) Synthesis of a-6: Under nitrogen protection, 4-bromo resorcinol 9.5 g, a-5 17.8 g, potassium carbonate 13.8 g, TBAB 1.0 g were sequentially added to a 100 ml three-necked flask.Pd(0)0.2g, ethanol 50mL, water 20mL, reflux and stirring for 5h,The reaction solution was acidified with dilute hydrochloric acid, extracted with toluene, and concentrated.Recrystallization from 2 times ethanol gave a pale yellow solid a-6.13.1 g, Y = 71.9%, GC = 99.18%. 7) Synthesis of a-7: A-6 10.9 g was added to a 100 ml three-necked bottle in turn.50mL of dichloromethane, 9.4g of tetrabutylammonium fluoride,The reaction was refluxed for 1 h, washed with water and concentrated to give a pale yellow solid a-7.8.1 g, Y = 92.0%, LC = 98.76%. 8) Synthesis of a: under nitrogen protection,Add a-75.8g to a 100ml three-necked bottle.50 mL of dichloromethane and 9.1 g of triethylamine.The polymerization inhibitor is 0.01 g of hydroquinone, and a mixed solution of 7.5 g of methacryloyl chloride and 15 mL of dichloromethane is added dropwise in an ice water bath, and the mixture is naturally added to room temperature and stirred for 0.5 h after the dropwise addition.The reaction solution is acidified with dilute hydrochloric acid, washed with water and concentrated.Recrystallization from 1x ethanol and 2 times n-heptane mixed solvent,Purified by silica gel column to obtain product a, 5.2g, Y=52.5%,LC = 99.90%.

The synthetic route of 1996-29-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Xi’an Ruili Electronic Materials Co., Ltd.; Li Chao; Zhao Wen; Zhang Yanli; Jin Linuo; (35 pag.)CN109503534; (2019); A;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Electric Literature of 50638-47-6, 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. 50638-47-6, name is 4-Bromo-2-chloro-1-methoxybenzene belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

To a magnetically stirring solution of 4-bromo-2-chloroanisole (0.50 g, 2.61 mmol) and 1- CYCLOPENTYL-2-PROPEN-1-OL (1.5 eq, 0.49 g, 3.88 mmol) in anhydrous N-methylpyrrolidinone (3.0 mL), under argon at room temperature, was added sodium bicarbonate (1.2 eq, 0.26 g, 3.10 mmol) followed by DICHLOROBIS (TRIPHENYLPHOSPHINE) PALLADIUM (II) (0.02 eq, 36.7 mg, 0.05 MMOL). The resulting mixture was heated to 140 C in an oil bath and maintained for 4 hours. The resulting dark reaction mixture was cooled to room temperature and poured into water (50 mL) and extracted with EtOAc (2 X 25 mL). The organics were washed with water (50 mL) and brine (50 mL) then dried over NA2SO4, filtered and concentrated. The crude residue was purified by flash chromatography (1% through 10% EtOAc in Hexanes) to yield the intermediate ketone as a slightly yellow oil (0.49 g, 79%).

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-Bromo-2-chloro-1-methoxybenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; PFIZER INC.; WO2004/74270; (2004); A2;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Synthetic Route of 2613-30-1, The chemical industry reduces the impact on the environment during synthesis 2613-30-1, name is 4-Chloro-2,5-difluoroaniline, I believe this compound will play a more active role in future production and life.

General procedure: To a solution of 1H-pyrrolo[3,2-H]quinoline-3-sulfonyl chloride (140 mg, 0.52 mmol) in pyridine (1.5 mL) was added 4-chloro-2,5-difluoroaniline (90 mg, 0.55 mmol). The reaction mixture was stirred at room temperature for 4h and then evaporated to dryness. The residue was triturated in a mixture of water/acetonitrile (8/2) and sonicated. The solid suspension was filtered, rinsed with water, dried under vacuum at 35C, to afford 105 mgof N-(4-chloro-2,5-difluorophenyl)-1 H-pyrrolo[3,2-h]quinoline-3-sulfonamide 1-118, as a beige solid.Yield: 50%.Basic LCMS Method 1 (ES): 394 (M+H), 99 % purity.1H NMR (400 MHz, DMSO-d6) 6 13.26 (s, 1H), 10.51 (s, 1H), 8.93 (dd, J = 4.4, 1.6 Hz,1 H), 8.46 (dd, J = 8.3, 1.6 Hz, 1 H), 8.04 – 7.65 (m, 3H), 7.59 (m, 1 H), 7.51 (dd, J = 9.8,6.8 Hz, 1H), 7.40 (dd, J = 10.4, 7.0 Hz, 1H).

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-Chloro-2,5-difluoroaniline, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; UCB PHARMA GMBH; MUELLER, Christa E.; PEGURIER, Cecile; DELIGNY, Michael Louis Robert; EL-TAYEB, Ali; HOCKEMEYER, Joerg; LEDECQ, Marie; MERCIER, Joel; PROVINS, Laurent; BOSHTA, Nader M.; BHATTARAI, Sanjay; NAMASIVAYAM, Vigneshwaran; FUNKE, Mario; SCHWACH, Lukas; GOLLOS, Sabrina; VON LAUFENBERG, Daniel; BARRE, Anais; (493 pag.)WO2018/122232; (2018); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

These common heterocyclic compound, 94-97-3, name is 5-Chloro-1H-benzo[d][1,2,3]triazole, 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. Safety of 5-Chloro-1H-benzo[d][1,2,3]triazole

General procedure: in EtOAc/MeOH (4:1) mixture solvent (2 mL), benzotriazoles 1 (0.3 mmol), sodium sulfinates 2 (0.54 mmol), NaBr (0.36 mmol) and mCPBA (0.39 mmol) were added successively. The suspension mixture was vigorously stirred at room temperature for 4 h. Upon completion, the reaction was quenched by addition of sat. aq. Na2S2O3 (2 mL), basified with sat. aq. Na2CO3(8 mL) and H2O (5 mL). The mixture was extracted with CH2Cl2 (3×5 mL) and the combined organic phase was dried over anhydrous Na2SO4, filtered, and concentrated under reduced pressure. The residue was then purified by TLC technique (3:1 (v/v) petroleum ether/ethyl acetate) to furnish sulfonylbenzotriazoles 3.

The synthetic route of 5-Chloro-1H-benzo[d][1,2,3]triazole has been constantly updated, and we look forward to future research findings.

Reference:
Article; Wu, Sixue; Zhang, Yikun; Yan, Jie; Synthetic Communications; vol. 46; 17; (2016); p. 1432 – 1437;,
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. 5013-77-4, name is N-Methyl-2,4-dichlorobenzylamine belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Application In Synthesis of N-Methyl-2,4-dichlorobenzylamine

General procedure: To a stirring solution of carboxylic acid (10 mmol, 1.0equiv) in dry DMF (10 mL) in a two-neck flask under argon atmosphere at -10 oC, HOBt (hydrate form, 1.76 g, 13 mmol,1.3 equiv) was added followed by the addition of DIPEA (2.26 mL, 13 mmol, 1.3 equiv) and EDCI (2.02 g, 13 mmol, 1.3equiv). The reaction mixture was stirred at -10 oC for 30 min before an appropriate amine (10 mmol, 1.0 equiv) was addedand allowed to warm to room temperature. After 16 h, the reaction mixture was treated with 10% citric acid solution (25mL) and extracted with DCM. The organic phase was washed with saturated NaHCO3 solution (2 ×), followed with waterand brine, dried over anhydrous Na2SO4, filtered, and evaporated in vacuo to remove solvents. The crude product waspurified by silica gel flash chromatography (EtOAc-Heptane).

The synthetic route of 5013-77-4 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Mai, Anh Hung; Pawar, Sonalika; De Borggraeve, Wim M.; Tetrahedron Letters; vol. 55; 33; (2014); p. 4664 – 4666;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics