Tag: M.W=100-200

A common compound: 108-37-2, name is 1-Bromo-3-chlorobenzene, belongs to chlorides-buliding-blocks compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below. 108-37-2

(Setting-Up and Reaction) To a 50 mL two-necked round-bottomed flask, [PdCl (pi-allyl) ]2 (10.8 mg, 0. 05 mol%) and cBRIDP (41.8 mg, 0.2 mol%) were added. A three-way stopcock was attached to the flask, and the inside was purged with nitrogen. Subsequently, anhydrous THF (5 mL) was added, and the mixture was shaken at room temperature for 1 minute and further diluted with anhydrous xylenes (20 mL) to prepare a catalyst solution (25 mL). On the other hand, to a 300 mL four-necked round-bottomed flask, a three-way stopcock, a Teflon-coated magnetic stirring bar, a condenser, a 50 mL dropping funnel, and a thermometer were attached, and the inside was purged with nitrogen. To this flask, carbazole (20.4 g, 178.8mmol, 1.03eq.), anhydrous xylenes (100 mL), and anhydrous THF (10 mL) were sequentially added, and the obtained reactant suspension was cooled to 5C by use of an ice-water bath. Subsequently, a MeMgCl/THF solution (3.02 mol/L, 40.0 mL, 120.8 mmol, 1.02 eq.) was placed in the dropping funnel, and added dropwise over 20 minutes, while the reactant suspension was being stirred, and the inside temperature was being kept at 20C or below. Then, the dropping funnel was rinsed with anhydrous xylenes (20 mL). Subsequently, 3-bromochlorobenzene (14.0 mL, 118.4 mmol, 1.0 eq.) and the catalyst solution (25 mL) were sequentially added to the reaction solution, and then the mixture was stirred for 1 hour under reflux (approximately 110C). Reaction Conversion: >99.9% (GC). (Post Treatment) After the obtained suspension had been cooled to room temperature, water (60 mL) and ammonium chloride (3.2 g, approximately 0.5 eq.) were added. The mixture was filtered by use of diatomaceous earth, the aqueous layer was separated (Aqueous Layer 1: pH=9), and further the organic layer was washed with water (60 mL) (Aqueous Layer 2: pH=7). The organic layer was concentrated under reduced pressure, and the obtained brown viscous liquid was purified by silica gel column chromatography (Eluent: n-hexane/toluene=4/1 to 2/1) to give 32.4 g of title compound (8) as a colorless viscous liquid. Isolated Yield: 98.5%. For exact measurement of the weight, a toluene solution of title compound (8) (25% by weight, 0.900 mmol/g) was prepared after the purification and used in the second step. 1H NMR (300 MHz, CDCl3): delta=8.13 (dt, J=7.5, 0.9 Hz, 2H), 7.58 (t, J=2.1 Hz, 1H), 7.56-7.38 (m, 8H), 7.35-7.25 (m, 2H). 13C NMR (75 MHz, CDCl3): delta=140.5, 140.0, 135.4, 130.8, 127.6, 127.2, 126.1, 125.2, 123.5, 120.4, 120.3, 109.6.

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, 108-37-2, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Takasago International Corporation; Nakayama, Yuji; Yokoyama, Naota; EP2937355; (2015); 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. 108-41-8, name is 1-Chloro-3-methylbenzene, This compound has unique chemical properties. The synthetic route is as follows., 108-41-8

General procedure: KBr (29.8 mg, 0.25 mmol, 1.0 equiv), 1-ethyl-4-nitrobenzene (1a) (41.6 mg, 0.275 mmol, 1.1 equiv), Oxone (153.9 mg, 0.25 mmol, 1.0 equiv), CH2Cl2 (0.25 mL) and H2O (180.0 mg, 0.18 mL, 40.0 equiv) were added, in accordance with the order, to a 15-mL oven-driedtube. The reaction tube was equipped with a magnetic stir bar and sealed with a Teflon-lined cap at once after the addition of the H2O. Then, the tube was placed on a magnetic stirrer (speed 300 rpm) and irradiated with a 0.5 W LED at a distance of 5 cm for 20 h at rt. After the reaction was finished, the reaction mixture was quenched with Na2SO3. Water (15 mL) was added and the mixture extracted with CH2Cl2 (3 ¡Á 5 mL). The organic phase was combined and dried with anhydrous Na2SO4. The solvent was evaporated under reduced pressure to give the crude product that was purified by flash column chromatography (petroleum ether/EtOAc mixtures). Compound 3a was obtained as a light yellow solid; yield: 53.6 mg (93%).

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Reference:
Article; Zhao, Mengdi; Li, Meiqi; Lu, Wenjun; Synthesis; vol. 50; 24; (2018); p. 4933 – 4939;,
Chloride – Wikipedia,
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Adding a certain compound to certain chemical reactions, such as: 626-43-7, name is 3,5-Dichloroaniline, belongs to chlorides-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 626-43-7, 626-43-7

EXAMPLE 6; Preparation of 1,3,5-triaminobenzene from 3,5-dichloroaniline; hydrolysis with sulfuric acid of the 1,3,5-triaminobenzene to phloroglucinol, and purification; A pressurized vessel is charged with 30 g (18.6 mmol) of 3,5-dichloroaniline and 1.5 g of copper chloride in 160 ml of 28% aqueous ammonia. The mixture is heated at 190 C. and under a pressure of 37 bars for 24 hours. The contents of the vessel are poured into 200 ml of water and then the excess ammonia is removed. Then 37 g of 98% sulfuric acid are added and the mixture is heated at 110 C. for 20 hours. Following filtration, the solution is concentrated to a third and then cooled in an ice bath until the phloroglucinol precipitates. The precipitate obtained is subsequently recrystallized from 350 ml of a water-ethanol (93 V-7 V) mixture.

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, 3,5-Dichloroaniline, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; PHV ANALYITIC; US2005/165256; (2005); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

6940-78-9, Adding some certain compound to certain chemical reactions, such as: 6940-78-9, name is 1-Bromo-4-chlorobutane, 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 6940-78-9.

Add p-nitrophenol (1.39g, 10mmol) and potassium carbonate (1.38g, 10mmol) to 25ml acetonitrile, then add dropwise1-Bromo-4-chlorobutane (1.7 ml, 15 mmol) was refluxed at 80 C overnight. After the reaction is completed, water is added to dissolve potassium carbonate, andExtract with ethyl acetate, wash the organic phase with saturated sodium bicarbonate and brine.Evaporation to dryness gave a white solid (1.98 g, yield 86%).The product was used directly in the next reaction without purification.

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 6940-78-9.

Reference:
Patent; Beijing Xinchen Pharmaceutical Technology Co., Ltd.; Yin Yuxin; Zhai Zheng; (37 pag.)CN109593064; (2019); A;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

A common heterocyclic compound, 6940-78-9, name is 1-Bromo-4-chlorobutane, molecular formula is C4H8BrCl, 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. 6940-78-9.

At 20 ~ 30 C, under stirring to N,N-dimethylformamide (1000 ml) was added 7-hydroxy-1H-quinolin-2-one (200.0 g) and potassium hydroxide (205.3 g, 1.2 eq), 240 ml of pure water was slowly added to the mixed solution at a controlled temperature of <40 C. The mixture was stirred at room temperature for about 15 minutes and 1-chloro-4-bromobutane (422 g, 2.0 eq) was added in one portion and then stirred at 40 C. for 5-6 h . The mixture was stirred for 1 h at room temperature and filtered. The cake was beaten by stirring in 1000 ml of water for 1 h, filtered, and the filter cake was refined in 10 times of methanol to obtain 240 g of the title compound (3) (yield: 77.0%). The synthetic route of 1-Bromo-4-chlorobutane has been constantly updated, and we look forward to future research findings. Reference:
Patent; Anhui Runsheng Pharmaceutical Co., Ltd.; Sun Mingzhe; Fang Cunjie; Zhao Dongsheng; Fang Congbin; Sun Yanbiao; Xu Kui; (4 pag.)CN106496206; (2017); A;,
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Chlorides – an overview | ScienceDirect Topics

2533-69-9, Adding a certain compound to certain chemical reactions, such as: 2533-69-9, name is Methyl 2,2,2-trichloroacetimidate, belongs to chlorides-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 2533-69-9.

To a suspension, cooled to 0 C., of 1.50 g (8.97 mmol) of N1-methyl-4-nitrobenzene-1,2-diamine in 40.0 ml of glacial acetic acid were added dropwise 1.22 ml (9.87 mmol) of methyl 2,2,2-trichloroacetimidate and the mixture was stirred at RT for 3 h. For workup, the mixture was added to water, and the solid was filtered off and washed with water. The solid was dried at 50 C. under high vacuum. This gave 2.50 g (93% of theory) of the title compound. LC-MS (Method 1): Rt=1.06 min; MS (ESIpos): m/z=296 (M+H)+. 1H NMR (400 MHz, DMSO-d6): delta [ppm]=4.20 (s, 3H), 8.00 (d, 1H), 8.35 (dd, 1H), 8.75 (d, 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, Methyl 2,2,2-trichloroacetimidate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; Fuerstner, Chantal; Ackerstaff, Jens; Straub, Alexander; Meier, Heinrich; Tinel, Hanna; Zimmermann, Katja; Tersteegen, Adrian; Zubov, Dmitry; Kast, Raimund; Schamberger, Jens; Schaefer, Martina; Boerngen, Kirsten; US2015/148340; (2015); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 7781-10-4, name is 4-Chloro-7-methyl-7H-pyrrolo[2,3-d]pyrimidine, belongs to chlorides-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 7781-10-4, 7781-10-4

General procedure: A typical procedure for the preparation of 3a:2-bromopropane (74 mg, 0.6 mmol) was added to a solution of 1a (92 mg, 0.6 mmol) and K2CO3 (110 mg, 0.8 mmol) in 5 mL DMF at 70 C. According to TLC the reaction went to completion after 4 h. The mixture was extracted with ethyl acetate (3 * 10 mL). The combined organic layers were washed with brine(10 mL), dried over anhydrous Na2SO4, filtered and concentrated to give the crude product 2a, which was added to a solution of amino-phenol(66 mg, 0.6 mmol) and Cs2CO3 (585 mg, 1.8 mmol) in 10 mL DMSO without further purification. After stirring for 6 h at 80 C, the mixture was cooled to room temperature and extracted with ethyl acetate (3 * 10 mL). The combined organic layers were washed with brine (10 mL), dried over anhydrous Na2SO4, filtered and concentrated to give the crude product, which was further purified by column chromatography(petroleum ether/ethyl acetate 2:1) to afford compound 3a as a brown solid(121 mg, 75% over two steps): 1H NMR (300 MHz, CDCl3) delta 8.44 (s, 1H), 7.16 (d, J = 3.6 Hz, 1H), 7.02 (d, J = 8.9 Hz, 2H), 6.73 (d, J = 8.9 Hz, 2H), 6.39 (d, J = 3.6 Hz, 1H), 5.11 (m, 1H), 3.70 (s, 2H), 1.51 (d, J = 6.8 Hz, 6H).; 13C NMR (100 MHz, d6-DMSO) delta 162.5, 151.5, 150.0, 146.3, 142.7, 124.5, 122.2, 114.3, 104.6, 98.0, 46.0, 22.3.; HRMS [M]+ calcd for C15H16N4O268.1324, found 268.1326. The purity of the compound was >98% by HPLC.

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-7-methyl-7H-pyrrolo[2,3-d]pyrimidine, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Liu, Yang; Fang, Jianping; Cai, Haiyan; Xiao, Fei; Ding, Kan; Hu, Youhong; Bioorganic and Medicinal Chemistry; vol. 20; 18; (2012); p. 5473 – 5482;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

13726-14-2, name is 4-Chloro-3-methoxyaniline, belongs to chlorides-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. 13726-14-2

5-Nitro-2-chloro aniline (50.0 g, 0.289 mol) in 30 % sulfuric acid (300 ml) was stirred at RT for 2 h. Sodium nitrite (21.0 g, 0.304 mol) in water (50 ml) was added slowly at 0C. After 15 mins, this solution was added slowly to dilute sulfuric acid (50 %, 250 ml) at 110 C. Stirring was continued for 15 min. The reaction mixture was cooled to RT, ice water was added, extracted with ethylacetate, washed with water, brine and dried over NA2SO4. The phenol product obtained upon concentration was purified by column chromatography. Yield 12.0 g, 24.0 %. [00153] K2CO3 (23.84 g, 0.172 mol) was added to 2-chloro-5- nitrophenol (10.0 g, 0.058 mol) in acetonitrile (100 ml) at RT. After cooling to 0 C, methyl iodide (19.6 g, 0.138 mol) was added slowly and the reaction mixture stirred at RT overnight. Water (100 ml) was added and the aqueous layer extracted with ethyl acetate. The organic layer was washed with water, brine and dried over NA2SO4. The product obtained upon concentration was purified by column chromatography to yield the ANISOLE (6.0 g, 55.55%). [00154] 2-CHLORO-5-NITRO ANISOLE (6.0 g, 0.032 mol) in MEOH (45 ml) was added slowly to stannous chloride (15.1 g, 0.08 mol) in conc. HCI (110 ml) at 40 C and the temperature was slowly raised to 50 C. Stirring was continued for 2 h. After cooling to RT, the reaction mixture was basified with 50 % NAOH solution, extracted by ethyl acetate, washed with water, then brine and dried over NA2SO4. 3-METHOXY-4-CHLOROANILINE was obtained upon concentration and was purified further by column chromatography. Yield : 4.0 g, 79.36 %. [00155] To 3-METHOXY-4-CHLOROANILINE (2.0 g, 0.0126 mol) in trichloroethylene (30 ml) was added BC13 (2.18 g, 1 M solution in DCM, 0.0188 mol) AT 0 C. After stirring for 10 min, 4-CYANOPYRIDINE (1.6 g, 0.0153 mol) and AIC13 (2.35 g, 0.018 mol) were added and the temperature was raised to RT, with further stirring for 30 min. The temperature was raised further to 85 C and maintained at the same temperature for 1 h. DCM was distilled off and the solution was stirred at 115 C for 4 h and then at RT over night. 3N HCI was added at RT and the reaction mixture REFLUXED for 1.5 h. The reaction mixture was allowed to cool and made basic using NAOH (6 N), diluted with water and extracted with DCM, washed with water, brine and dried over NA2SO4. The crude title compound was obtained upon concentration and was purified by column chromatography. Yield : 0.50 g, 15 %.

Statistics shows that 13726-14-2 is playing an increasingly important role. we look forward to future research findings about 4-Chloro-3-methoxyaniline.

Reference:
Patent; CHEMOCENTRYX; WO2004/46092; (2004); A2;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

6940-78-9, Adding some certain compound to certain chemical reactions, such as: 6940-78-9, name is 1-Bromo-4-chlorobutane, 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 6940-78-9.

General procedure: General procedure for the preparation of omega-naphthyloxyhalo alkanes (3a-c) involves refluxing of mixture of beta-naphthol (1) (20 g, 0.14 mol), anhydrous K2CO3 (100 g, in excess) and bromochloroalkane 2 (0.14 mol) in dry acetone (200 mL) for12-15 h. Reaction mixture was filtered and filtrate was concentrated to get oily compound, which was crystallized with benzene-hexane to give the colourless crystals of pure desired compound (Scheme-I) [48].

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 6940-78-9.

Reference:
Article; Zaidi, Sadaf; Chaturvedi, Devdutt; Saxena, Mridula; Srivastava, Richa; Asian Journal of Chemistry; vol. 31; 10; (2019); p. 2201 – 2210;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

26487-67-2, 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. 26487-67-2, name is 1-(2-Chloroethyl)azepane hydrochloride belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

To a solution of 1,1-bis(4-hydroxyphenyl)-2-butylhex-1-ene (69.1 mg, 0.213 mmol) in DMF (2.13 mL) at 0 ¡ãC was added 55percent sodium hydride (dispersion in paraffin liquid, 74.4 mg, 1.71 mmol). The reaction mixture was stirred for 15 min at 50 ¡ãC and then N-(2-chloroethyl)hexahydro-1H-azepine hydrochloride (139 mg, 0.702 mmol) was added in portions at room temperature. After the reaction mixture had been stirred for 3 h at 50 ¡ãC, saturated aqueous ammonium chloride was added at 0 ¡ãC. The mixture was extracted with dichloromethane and the organic layer was dried over sodium sulfate. After filtration of the mixture and evaporation of the solvent, the crude product was purified by thin layer chromatography on silica (eluant; ammoniacal chloroform/methanol = 30/1) to afford RID-F-S*23 (compound 18) (118 mg, 96percent) as an orange oil

The synthetic route of 1-(2-Chloroethyl)azepane hydrochloride has been constantly updated, and we look forward to future research findings.

Reference:
Article; Hasegawa, Makoto; Yasuda, Yukari; Tanaka, Makoto; Nakata, Kenya; Umeda, Eri; Wang, Yanwen; Watanabe, Chihiro; Uetake, Shoko; Kunoh, Tatsuki; Shionyu, Masafumi; Sasaki, Ryuzo; Shiina, Isamu; Mizukami, Tamio; European Journal of Medicinal Chemistry; vol. 71; (2014); p. 290 – 305;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics