Month: June 2021

Reference of 95-81-8, A common heterocyclic compound, 95-81-8, name is 2-Chloro-5-methylaniline, molecular formula is C7H8ClN, 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.

EXAMPLE 62 N-((4-Chlorophenyl)methyl)-4-hydroxy-5-methyl-3-quinolinecarboxamide [] A mixture of 2-chloro-5-methylaniline (2.83 g) and diethyl ethoxymethylenemalonate (4.04 mL) is heated at 135 C for 2 h. The resulting mixture is diluted with diphenyl ether (40 mL) and heated to reflux with a Dean-Stark trap for 1 h. The mixture is allowed to cool to rt and is then poured into hexane (50 mL). The solid is filtered and is washed with hexane (20 mL) and hexane/diethyl ether (1/1, 2 x 30 mL) to afford 4.89 g of the 8-chloro-6-methyl-quinolinecarboxylate ethyl ester. The ethyl ester (2.0 g) is dissolved in acetic acid (150 mL) along with NaOAco3 H2O (1.12 g) and 5% palladium on carbon (750 mg). The mixture is placed under hydrogen pressure (28 psi) in a Parr hydrogenator for 3 h. The mixture is filtered through a plug of celite, concentrated in vacuo, and suspended in water (10 mL). The crude product is filtered, washed with water, and recrystallized (DMF) to afford 964 mg of the 5-methyl-quinolinecarboxylate ethyl ester. The resulting ester (463 mg) and 4-chlorobenzylamine (2.43 mL) are heated at 190 C for 1 h. The resulting mixture is diluted with toluene (5 mL) and allowed to cool to rt affording a white solid. The crude product is filtered, washed with toluene (2 mL) followed by hexane (4 mL), and then recrystallized successively from acetic acid/water then ethyl acetate to afford 426 mg of the title compound as a white solid. Physical characteristics are as follows: Mp 205-6 C.1H NMR (300 MHz, DMSO) delta 12.50, 10.46, 8.64, 7.55, 7.47, 7.37, 7.15, 4.51, 2.83.13C NMR (100 MHz, DMSO) delta 179.47, 165.26, 143.30, 141.17, 140.60, 139.33, 132.26, 131.80, 129.75, 128.77, 127.97, 125.04, 117.56, 112.18, 41.84, 24.21IR (mull) 3404, 2924, 2855, 1645, 1628, 1604, 1574, 1545, 1498, 1467, 1459, 1342, 1224, 1170, 1097, 1016, 816, 783, 75 cm-1.HRMS (FAB) Found, 326.0803.MS (ESI-) for C18H15ClN2O2m/z 325 (M-H)-.

The synthetic route of 95-81-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Pharmacia & Upjohn Company LLC; EP1042295; (2005); B1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 6276-54-6, name is 3-Chloropropan-1-amine hydrochloride, 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 6276-54-6, category: chlorides-buliding-blocks

To a solution of 3-chloropropan-1-amine hydrochloride salt (1.00 g, 7.69 mmol) in water (4ml) was added NaN3 (1.49 g, 22.7 mmol) and the reaction was heated at 80 C for 15 h. Thesolution was basified with KOH (1.10 g, 19.2 mmol) and extracted with diethyl ether (3 × 5 ml). Thecombined organics were dried over anhydrous Na2SO4, filtered and the solvent was removed (almost todryness) in vacuo to give 3-azidopropan-1-amine as a colourless oil (0.761 g, quant.).

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-Chloropropan-1-amine hydrochloride, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Hanna, Jill R.; Allan, Christopher; Lawrence, Charlotte; Meyer, Odile; Wilson, Neil D.; Hulme, Alison N.; Molecules; vol. 22; 5; (2017);,
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. 13918-92-8, name is 2,4-Difluorobenzene-1-sulfonyl chloride belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Product Details of 13918-92-8

To a cooled solution of 17 (4.0 g, 19.8 mmol) in pyridine (40 mL) was added 2,4-difluorobenzenesulfonyl chloride (18) (3.2 mL, 23.8 mmol) dropwise at 0 C. After the reaction mixture was allowed to warm to rt and stirred overnight, it was diluted with cold water. The precipitate was collected by filtration, washed with water, dried to afford 19 (3.42 g, 46%) as a pale pink solid, mp 154-156 C. 1H NMR (CDCl3) delta 7.91-7.88 (m+d, J = 2.0 Hz, 2H, Ar-H), 7.82 (d, J = 2.0 Hz, 1H, Ar-H), 7.22 (br s, 1H, NH), 7.00-6.92 (m, 2H, Ar-H), 3.90 (s, 3H, OCH3).

The synthetic route of 13918-92-8 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Wang, Min; Gao, Mingzhang; Miller, Kathy D.; Sledge, George W.; Zheng, Qi-Huang; Bioorganic and Medicinal Chemistry Letters; vol. 22; 4; (2012); p. 1569 – 1574;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Some common heterocyclic compound, 2533-69-9, name is Methyl 2,2,2-trichloroacetimidate, molecular formula is C3H4Cl3NO, 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. name: Methyl 2,2,2-trichloroacetimidate

A solution of 3,4-dimethylbenzene-1,2-diamine (1.0 g, 7.34 mmol) in acetic acid (10 ml) was treated with methyl-2,2,2-trichloroacetimidate (1.0 ml, 8.07 mmol) and the resulting solution was left to stir at room temperature for 16 hours. The reaction mixture was poured onto ice (100 g) and then extracted with dichloromethane (100 ml). The organic phase was separated, dried (sodium sulfate) and the solvent removed in vacuo. The residue was triturated with diethyl ether and the title compound isolated by filtration (360 mg) as a brown solid. The material was used crude in the next step with no further characterization.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2533-69-9, its application will become more common.

Reference:
Patent; Lane, Charlotte Alice Louise; Price, David Anthony; US2006/111416; (2006); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 14752-66-0, name is Sodium 4-chlorobenzenesulfinate, 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 14752-66-0, Application In Synthesis of Sodium 4-chlorobenzenesulfinate

General procedure: To a solution of N-methylindoles (1.0mmol), sodium aryl sulfonates (0.5mmol), catalyst I2 (0.75mmol) and tert-Butyl hydroperoxide (1.5mmol) in methanol (2mL) were added. The reaction mixture was stirred at 80C for 12h. Then the reaction mixture was cooled to room temperature, diluted with brine (15mL) and extracted with EtOAc (3×25mL). The organic layer dried over anhydrous MgSO4 and concentrated in vacuo. The residue was further purified by column chromatography on silica gel (Petroleum ether/EtOAc=5:1) to afford the compounds 6a, 7a-b, 8a-h, 9a-k, 10a-d with yield of 9%-95%.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Sodium 4-chlorobenzenesulfinate, and friends who are interested can also refer to it.

Reference:
Article; Xia, Qinqin; Bao, Xiaodong; Sun, Chuchu; Wu, Di; Rong, Xiaona; Liu, Zhiguo; Gu, Yugui; Zhou, Jianmin; Liang, Guang; European Journal of Medicinal Chemistry; vol. 160; (2018); p. 120 – 132;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Related Products of 104-52-9,Some common heterocyclic compound, 104-52-9, name is 3-Phenylpropyl Chloride, molecular formula is C9H11Cl, 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.

Aluminum chloride (160 g, 1.2 mol, 2 q) was added to a 500 ml three-necked flask to keep the reaction solution at a temperature of not higher than -15 C. Pre-mixed 3-chlorophenyl propane (93 g, 0.6 mol, lq) and n-octanoyl chloride (116 g, 0.72 mol, 1.2 eq). After completion of the dropwise addition, the reaction was complete at -5 C until the reaction was complete [reaction takes about 8 to 14 hours, HPLC detection: 3-chlorophenylpropane The mixture was slowly poured into 1200 ml of 5% hydrochloric acid and extracted with ethyl acetate (200 ml x 3 times). The organic layers were combined and the organic layer was washed with saturated brine, dried over anhydrous sodium sulfate (50 g) was dried and filtered, and the filtrate was concentrated at about no more than 40 C to give a yellow oil to octanoylchloropropylbenzene (152 g, HPLC purity 95.86% yield 90%).

The synthetic route of 104-52-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CHENGDU HONGDA PHARMACEUTICAL CO., LTD.; KE, XIAO; CHANG, HEXI; YE, YONG; (13 pag.)CN103804123; (2016); B;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 1871-57-4, name is 3-Chloro-2-chloromethyl-1-propene, A new synthetic method of this compound is introduced below., Safety of 3-Chloro-2-chloromethyl-1-propene

Example 3 12,13-(2-methylene-propan-1,3-yl)-6,7,12,13-tetrahydro-5-oxo-5H-indolo[2,3-a]pyrrolo[3,4-c]carbazole (Compound 22) 12,13-(2-hydroxymethyl-propan-1,3-yl)-6,7,12,13-tetrahydro-5-oxo-5H-indolo[2,3-a]pyrrolo[3,4-c]carbazole (Compound 23) 9-hydroxymethyl-12,13-(2-hydroxymethyl-propan-1,3-yl)-6,7,12,13-tetrahydro-5-oxo-5H-indolo[2,3-a]pyrrolo[3,4-c]carbazole (Compound 212) Compound 1c (1.56 g, 5.0 mmol, 1.0 equiv) was added to Cs2CO3 (4.89 g, 15.0 mmol, 3.0 equiv) in DMF (20 mL) under N2 at room temperature. The mixture was stirred for 5 min, then 3-chloro-2-chloromethyl-prop-1-ene (625 mg, 5.0 mmol, 1.0 equiv) was added. The mixture was stirred at rt for 24 hours and poured into H2O (200 mL). The resulting yellow solid was filtered and washed with H2O (50 mL×2) and Et2O/hexane (1:1, 50 mL×3), then dried in vacuo to provide Compound 22 (1.46 g, 80%) as a yellow solid. 1H NMR: (d6-DMSO) delta 4.96 (s, 2H), 5.28 (s, 2H), 5.30 (s, 2H), 5.80 (s, 2H), 7.28 (t, 1H, J=8.1 Hz), 7.37 (t, 1H, J=7.2 Hz), 7.52 (t, 1H, J=8.1 Hz), 7.57 (t, 1H, J=8.1 Hz), 7.81 (d, 1H, J=8.1 Hz), 7.87 (d, 1H, J=7.8 Hz), 8.07 (d, 1H, J=7.2 Hz), 8.53 (s, 1H), 9.31 (d, 1H, J=7.8 Hz). MS m/z 386 (M+Na), 364 (M+H).

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:
Patent; Wilson, Lawrence J.; Murray, William V.; Yang, Shyh-Ming; Yang, Cangming; Wang, Bingbing; US2007/249590; (2007); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Electric Literature of 1303587-99-6, 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. 1303587-99-6, name is 2-Chloro-7,8-dihydro-6H-pyrimido[5,4-b][1,4]oxazine belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Synthesis ofN-(3-methoxy-4-(2-methylpyridin-4-yl) phenyl)-, 8-dihydro-6H-pyrimido [5, 4- b] [I, 4] oxazin-2-amine [0350] To a stirred solution of 2-chloro-7, 8-dihydro-6H-pyrimido [5, 4-b] [1, 4] oxazine (1 g, 5.81 mmol) in isopropyl alcohol (20 mL) under argon atmosphere were added 3- methoxy-4-(2-methylpyridin-4-yl) aniline (1.2 g, 5.81 mmol) and concentrated hydrochloric acid (12M, 0.5 mL) at RT. The reaction mixture was stirred at 120 C for 48 h in a sealed tube. After completion of the reaction (monitored by TLC), the volatile components were removed in vacuo. The resultant residue was basified with a saturated sodium bicarbonate solution (50 mL) and extracted with a 10% MeOH:CH2Cl2 solution (2 x 50 mL). The combined organic extracts were dried over sodium sulfate, filtered and concentrated in vacuo. The crude material was purified by silica gel column chromatography using 6% MeOH:CH2Cl2 to afford N-(3-methoxy-4-(2-methylpyridin-4-yl) phenyl)-7, 8-dihydro-6H- pyrimido [5, 4-b] [1, 4] oxazin-2-amine (950 mg, 47%) as a pale yellow solid. 1H-NMR (DMSO-d6, 500 MHz): delta 8.96 (s, IH), 8.36-8.35 (m, IH), 7.73 (s, IH), 7.51 (s, IH), 7.37 (d, 2H), 7.33 (s, IH), 7.29-7.28 (m, IH), 7.21 (d, IH), 4.07-4.05 (m, 2H), 3.78 (s, 3H), 3.45-3.43 (m, 2H), 2.47 (s, 3H); LC-MS: 350.2 (M+1); (column; X-Bridge C-18 (50 3.0 mm, 3.5 mupiiota); RT 2.47 min. 0.05% aq TFA: ACN; 0.80 mL/min); UPLC (column; Acquity UPLC BEH C-18 2.1 X 50 mm, 1.7 mupiiota); RT 1.20 min. ACN: 0.025% TFA (Aq); 0.50 mL/min; TLC: 10% MeOH:CH2Cl2 (R/. 0.6).

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, 2-Chloro-7,8-dihydro-6H-pyrimido[5,4-b][1,4]oxazine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; FORUM PHARMACEUTICALS INC.; BURNETT, Duane, A.; BURSAVICH, Matthew, Gregory; MCRINER, Andrew, J.; WO2015/66697; (2015); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Synthetic Route of 63624-28-2, These common heterocyclic compound, 63624-28-2, name is 2,4-Dimethoxybenzene-1-sulfonyl chloride, 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: A mixture of ethyl 6-amino-9-ethyl-1-methyl–carboline-3-carboxylate 11a (1.0 mmol) and 3,4-dimethoxybenzene sulfonylchloride (1.0 mmol) in DMF (5 mL) was stirred for 5min at room temperature, followed by the addition of pyridine(4.0 mmol) was added. The mixture was stirred for an additional0.5 h. After adding ice water (10 mL), the mixture wasextracted with EtOAc (320 mL). The organic phase waswashed with brine (220 mL), dried over anhydrous Na2SO4,and concentrated in vacuum. The residue was purified oversilica column chromatography using petroleum ether (PE) :EtOAc (1:1, v/v) as eluent to afford the title compound 12a.

Statistics shows that 2,4-Dimethoxybenzene-1-sulfonyl chloride is playing an increasingly important role. we look forward to future research findings about 63624-28-2.

Reference:
Article; Chen, Jing; Du, Wenting; Tao, Xuefen; Huang, Jiawei; Song, Yuliang; Ying, Huazhou; Letters in drug design and discovery; vol. 10; 9; (2013); p. 879 – 885;,
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. 210532-25-5, name is 3,5-Difluorobenzene-1-sulfonyl chloride belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. COA of Formula: C6H3ClF2O2S

To a solution of 3,5-difluorobenzenesulfonyl chloride (25 g, 0.117 mol) in THF (150 rnL) was added 35% aq. NH4OH (120 rnL) over 1 h in an ice-bath. After the reaction was complete, it was evaporated in vacuo. To a solution of this residue in water (150 mL) was added 2N HCl (1 mL). After stirring 1 h, the reaction mixture was filtered and dried under high vacuum to give 3,5-difluorobenzenesulfonamide as a light brown solid (19.9 g, 88%). 1H NMR (400MHz, CDCl3) delta 7.49-7.44 (m, 2H), 7.04-6.99 (m, 2H).

The synthetic route of 210532-25-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; EXELIXIS, INC.; BOLLU, Venkataiah; BOREN, Brant, Clayton; DALGARD, Jackline, Eve; FLATT, Brenton, T.; HAQ, Nadia; HUDSON, Sarah; MOHAN, Raju; MORRISSEY, Michael; PRATT, Benjamin; WANG, Tie-lin; WO2010/93845; (2010); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics