Tag: M.W=100-200

Reference of 93-50-5,Some common heterocyclic compound, 93-50-5, name is 4-Chloro-2-methoxyaniline, molecular formula is C7H8ClNO, 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 38; 3-Biphenyl-4-yl-4-(4-chloro-2-methochiyphenyl)-5-methyl-4/-/-1 ,2,4-triazole; A mixture of 2-biphenyl-4-yl-5-methyl-1 ,3,4-oxadiazole [(1g, 4.2mmol), Bioorganic & Medicinal Chemistry, 2002, 10, 1905], the product of preparation 37 (800mg, 5.04mmol) and para-toluenesulfonic acid (200mg) in xylene (2OmL) was heated at 15O0C for 10 hours. Further para-toluenesulfonic acid (100mg) was added at regular intervals, until all of the starting material was consumed. After heating at 15O0C for 4.5 hours, the reaction mixture was diluted with 2M hydrochloric acid, extracted with ethyl acetate and concentrated in vacuo. The residue was purified by column chromatography on silica gel, eluting with EPO dichloromethane:methanol:0.88 ammonia, 98:2:0.2. The appropriate fractions were evaporated under reduced pressure and the residue was triturated with ethyl acetate (x3) to afford the title compound as a pale brown solid in 51% yield, 860mg.1HNMR(400MHz, CDCI3) delta: 2.30(s, 3H), 3.74(s, 3H), 7.04-7.10(m, 3H), 7.32-7.57(m, 9H); LRMS APCI m/z 376 [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 4-Chloro-2-methoxyaniline, its application will become more common.

Reference:
Patent; PFIZER LIMITED; WO2006/100588; (2006); A1;,
Chloride – Wikipedia,
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Electric Literature of 13726-14-2, 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. 13726-14-2, name is 4-Chloro-3-methoxyaniline, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: N-Benzylpiperidone (1 g, 5.2 mmol, 1 equiv), 3, 4 difluoroaniline (0.52 mL, 5.2 mmol, 1 equiv) and sodium sulfate (3.7 g, 26.4 mmol, 5 equiv) were suspended in dichloromethane (20 mL). Sodium triacetoxyborohydride (1.3 g, 6.33 mmol, 1.2 equiv) was added and the reaction mixture was stirred at room temperature overnight. Aqueous sodium hydrogen carbonate was added followed by stirring for 30 min. The reaction mixture was extracted with dichloromethane and the combined organic phases were washed with brine, dried over sodium sulfate, filtrated and concentrated in vacuo. The residue obtained upon evaporation of solvent was chromatographed over silica gel and eluted with 35% ethyl acetate/hexane to give the 26 as a light yellow colored solid (1.2 g, 75% yield).

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

Reference:
Article; Deekonda, Srinivas; Wugalter, Lauren; Kulkarni, Vinod; Rankin, David; Largent-Milnes, Tally M.; Davis, Peg; Bassirirad, Neemah M.; Lai, Josephine; Vanderah, Todd W.; Porreca, Frank; Hruby, Victor J.; Bioorganic and Medicinal Chemistry; vol. 23; 18; (2015); p. 6185 – 6194;,
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Application of 6775-78-6, These common heterocyclic compound, 6775-78-6, name is 6-Chloroimidazo[1,2-b]pyridazine, 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.

3. 3-Bromo-6-chloro-imidazon , 2-blpyridazine (5)[0140] The 6-Chloro-imidazo[1 ,2-b]pyridazine (4) (500 mg, 0.0032 mol) was taken in glacial acetic acid (5 ml) and bromine (0.4 ml) was added slowly at room temperature. After 20 minutes, solid precipitated out and was filtered. The solid was washed with ether (3 x 15 ml) and dried under air to give 3-Bromo-6-chloro-imidazo[1 ,2-b]pyridazine (5) (400mg, yield = 60%).

The synthetic route of 6775-78-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SUPERGEN, INC.; WO2008/58126; (2008); A2;,
Chloride – Wikipedia,
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Synthetic Route of 26487-67-2,Some common heterocyclic compound, 26487-67-2, name is 1-(2-Chloroethyl)azepane hydrochloride, molecular formula is C8H17Cl2N, 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 solution of 1,1-bis(4-hydroxyphenyl)-2-hexyloct-1-ene (40.0 mg, 0.105 mmol) in DMF (1.80 mL) at 0 °C was added 55percent sodium hydride (dispersion in paraffin liquid, 36.7 mg, 0.841 mmol). The reaction mixture was stirred for 1 h at 50 °C and then N-(2-chloroethyl)hexahydro-1H-azepine hydrochloride (68.7 mg, 0.347 mmol) was added in portions at room temperature. After the reaction mixture had been stirred for 3 h at 50 °C, saturated aqueous ammonium chloride was added at 0 °C. 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 = 9/1) to afford RID-F-S*24 (compound 16) (57.4 mg, 87percent) as a pale yellow oil

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1-(2-Chloroethyl)azepane hydrochloride, its application will become more common.

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;,
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Related Products of 2533-69-9, 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. 2533-69-9, name is Methyl 2,2,2-trichloroacetimidate belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Step E4-[(4, 6- dicyclopropyl- 7-m ethyl- 1 H-benz imidazol-2-yl)carbon yl]-1-(trans-4- hydroxycyclohexyl)-2- piperazinone[00278] 4, 6-dicyclopropyl-3-methyl-1 , 2-benzenediamine (167 mg, 0.826 mmol) was dissolved in acetic acid (10 ml) before methyl 2,2,2-trichloromethylacetimidatate (0.146 ml, 1.16 mmol) was added drop-wise. The mixture was stirred at room temperature until the reaction was complete (~3 hours). The reaction was diluted with ethyl ether and then water added. The mixture was extracted 2 times with ethyl ether. The combined organic layers were washed with brine, dried over sodium sulfate, and concentrated. The residue was dissolved in acetonitrile (5 ml) before water (1.7 ml) was added. 1-(trans-4-hydroxycyclohexyl)-2-piperazinonehydrochloride (370 mg, 1.58 mmol) was added followed by drop-wise addition of potassium carbonate (4M) (0.789 ml, 3.15 mmol). The mixture was stirred for 1 hour. LC-MS showed none of the amide product, but the 2-carboxylic acid was observed. The reaction was concentrated and N,N-dimethylformamide (3 mL) added to the residue. N,N- diisopropylethylamine (0.551 ml, 3.15 mmol) was added followed by N-[(dimethylamino)(3H- [1 ,2,3]triazolot4,5-b]pyridin-3-yloxy)methylidene]-N-methylmethanaminium hexafluorophosphate (HATU) (360 mg, 0.946 mmol). The mixture was stirred for 2 hours and quenched with brine. The mixture was extracted 3 times with ethyl acetate. The combined organic layers were washed with brine, dried over sodium sulfate, and concentrated. The residue was purified by silica chromatography eluting with a gradient of 0% to 10% methanol in dichloromethane.Fractions were concentrated to leave the title compound (62 mg, 18%) as a white solid. LCMS: m/z 437 (M+1).

The synthetic route of Methyl 2,2,2-trichloroacetimidate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXOSMITHKLINE LLC; BANKA, Anna; CATALANO, John G; FANG, Jing; PEAT, Andrew James; TAI, Vincent; TURNER, Elizabeth; WO2011/97491; (2011); A1;,
Chloride – Wikipedia,
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Some common heterocyclic compound, 33050-38-3, name is 3,6-Dichloro-[1,2,4]triazolo[4,3-b]pyridazine, molecular formula is C5H2Cl2N4, 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: C5H2Cl2N4

c) 3-Chloro-6-(4-fluorophenyl)-1,2,4-triazolo[4,3-b]pyridazine may be prepared in the following manner: A mixture of 4.16 g of 4-fluorophenylboronic acid, 9.37 g of barium hydroxide octahydrate, 2.20 g of [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) as a complex with dichloromethane (1:1) and 5.1 g of commercial 3,6-dichloro[1,2,4]triazolo[4,3-b]pyridazine in 40 cm3 of N,N-dimethylformamide containing 10 cm3 of water is heated in a bath at 80 C. for 1.5 hours. The beige-brown suspension obtained is cooled to 20 C. and then poured into about 200 cm3 of water. The insoluble material is filtered off by suction and washed successively with water and ether, and then dried under vacuum at 20 C. The resulting beige-coloured solid is slurried in dichloromethane, filtered off by suction and dried under vacuum at 20 C. 1.24 g of 3-chloro-6-(4-fluorophenyl)-1,2,4-triazolo[4,3-b]pyridazine are thus obtained.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 33050-38-3, its application will become more common.

Reference:
Patent; SANOFI; US2012/165326; (2012); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Synthetic Route of 1871-57-4,Some common heterocyclic compound, 1871-57-4, name is 3-Chloro-2-chloromethyl-1-propene, molecular formula is C4H6Cl2, 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 1 L flask at 0 C was added 160 mL of methanol. The solution was kept under 30 C as Na metal (5.10 g, 221.24 mmol) was added in small portions. After all the sodium had reacted, 4-hydroxythiophenol (25.0 g, 2.2 eq) was added to the solution of sodium methoxide. The solution was heated to reflux and 3-chloro-2-chloromethyl-1-propene (11.26 g, 1 eq) was added dropwise over 1 hour. The solution was allowed to reflux overnight. The solution was cooled to 25 C, filtered, and reduced in vacuo to remove the methanol. The crude material was taken up in 500 mL of water and extracted with ether (4×150 mL). The ether layer was washed with 1N HCl, water, brine, and dried over sodium sulfate. The organic layer was reduced in vacuo to a crude orange oil. The oil was purified by flash chromatography 90:10 hexanes/ethyl acetate to yield 23.52 g of a colorless oil. Yield 85.8%. 1H NMR (400 MHz, CDCl3, delta): 7.23 (m, 4H, Ar-H), 6.74 (m, 4H, Ar-H), 5.84 (5, 2H, Ar-OH), 4.70 (5, 2H, C?CH2), 3.57 (5, 4H, CH2); 13C NMR (400 MHz, CDCl3, delta): 155.3 (C1), 140.45 (C10), 138.6 (C5), 134.3 (C8), 132.7 (C4), 126.0 (C7), 116.5 (C3), 116.0 (C6), 40.63 (C11); MS (ESI, m/z): [M+Li]+ calcd for C16H16O2S2, 344.3. found, 344.3.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3-Chloro-2-chloromethyl-1-propene, its application will become more common.

Reference:
Patent; Fenoli, Christopher R.; Bowman, Christopher N.; US2014/303391; (2014); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 20850-43-5, name is 5-(Chloromethyl)benzo[d][1,3]dioxole, 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 20850-43-5, Quality Control of 5-(Chloromethyl)benzo[d][1,3]dioxole

Preparation of 13-benzodioxol-5-ylmetllel propyl sulfone 5. 0 g of 5-(chloromethyl)-1, 3-benzodioxol was dissolved in 20 ml of anhydrous tetrahydrofuran and 20 ml of diethyl ether and then added to magnesium at 0C, and reacted for 10 minutes. The reactant was heated to 50C and reacted for 1 hour. The reaction mixture was cooled to 0C and then slowly added to a flask containing [1, 3-bis (diphenylphosphino) propane] nickel (II) dichloride as a catalyst. After the addition of 2.8 ml propane sulfonyl chloride, the mixture was reacted for 30 minutes, then the reactant was heated to 50C and reacted for 1 hour. Then, its pH was adjusted to 7 with dilute hydrochloric acid. The resulting mixture was extracted with diethyl ether and distilled water, dried over anhydrous magnesium sulfate and the solvent was removed. The residue was fractionated by column chromatography using ethyl acetate: n-hexane (1: 3), to give 0.8 g of the title compound of the following formula lc (Rf: 0.35, Yield: 7%). [Chemical Formula lc] The compound was dissolved in CDC13 and TMS and then characterized by H NMR spectroscopy. The result is as follows ; ‘H NMR S : 1. 16-1. 19 (t, 3H, J=7. 0Hz), 2.10-2. 15 (q, 2H, 7.4Hz), 2. 81 (s, 2H), 3.66-3. 69 (t, 2H, J=7.8Hz), 5.94 (s, 2H), 6.61-6. 63 (d of d, 1H), 6.68 (s, 1H), 7.28 (d, 1H, J=0.8).

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, 5-(Chloromethyl)benzo[d][1,3]dioxole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; HAN, Sang Min; LEE, Myung Hee; CHOI, Won Chul; WO2005/70915; (2005); 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. 14752-66-0, name is Sodium 4-chlorobenzenesulfinate belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Formula: C6H4ClNaO2S

The reaction was conducted with Pd(OH)2 (1.4 mg, 0.01 mmol), DABCO (2.3 mg, 0.02 mmol),sodium 4-chlorobenzenesulfinate (1f, 79.2 mg, 0.4 mmol), (E)-4-phenylbut-3-en-2-one (2a, 29.2mg, 0.2 mmol) and charged with argon (1 atm). TFA (0.1 mL, 6.7 equiv) and 1,4-dioxane (0.2 mL),H2O (0.2 mL) were added to the sealed reaction vessel by syringe. The resulting solution wasstirred at 120 C for 20 h. After cooling to room temperature, the volatiles were removed undervacuum and the residue was purified by column chromatography (silica gel, petroleum ether/ethylacetate = 30:1) to give 3p as pale yellow oil; yield 74%.

The synthetic route of 14752-66-0 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Chen, Wen; Zhou, Xianya; Xiao, Fuhong; Luo, Jiaying; Deng, Guo-Jun; Tetrahedron Letters; vol. 53; 33; (2012); p. 4347 – 4350;,
Chloride – Wikipedia,
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Reference of 2533-69-9, 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. 2533-69-9, name is Methyl 2,2,2-trichloroacetimidate belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Example 7; Synthesis of Compounds According to Formula (4); [00528] 5-bromo-2-(trichloromethyl)-lH-benzimidazole 2; To a solution of 4- bromo-o-phenylenediamine 1 (2.52Og, 13.5 mmol) in acetic acid (35mL) cooled to 0 0C was added methyl trichloroacetimidate (2.64Og, 15 mmol) under N2 atmosphere and resulting reaction mixture was stirred at room temperature for 3h. Diluted with water (200 mL) and resulting precipitate was filtered , washed with water (100 mL), dried in vacuum oven at 40 0C to give 5-bromo-2-(trichloromethyl)-lH-benzimidazole (4.1g, 97%). 1H NMR (300 MHz, DMSOd6) : 57.48 (d, J= 6.0 Hz, 1 H), 7.63 (d, J= 6.0 Hz, 1 H), 7.88 (s, 1 H); LCMS mlz 315 (M + H+), ELSD 100%. Reference: Louvet, P.; Lallement, G.; Pernot-Marino, L; Luu- Duc, C; Blanchet, G. Eur. J.Med.Chem. 1993, 28, 71-75.

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; CHEMBRIDGE RESEARCH LABORATORIES, INC.; WO2007/56155; (2007); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics