Tag: M.W=100-200

Synthetic Route of 10061-02-6, A common heterocyclic compound, 10061-02-6, name is trans-1,3-Dichloropropene, molecular formula is C3H4Cl2, 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.

Eine geruehrte Loesung von 77,7 ml Diisopropylamin und 200 ml Tetrahydrofuran wird auf -20 C gekuehlt und waehrend 15 Minuten mit 200 ml 2,5 M n-Hexyllithiumloesung (in Hexan) versetzt. Die Loesung wird 15 Minuten bei -20 C nachgeruehrt und anschliessend wird waehrend 30 Minuten eine Loesung von 75,3 ml Isovaleriansaeureethylester in 80 ml Tetrahydrofuran zugetropft. Die Loesung wird 10 Minuten nachgeruehrt und dann waehrend 10 Minuten bei -20 C mit 80 ml DMPU versetzt. Zugabe von 8,2 g Natriumiodid und 19,5 g trans-1,3-Dichlorpropen. Das Reaktionsgemisch wird noch 23 Stunden bei – 20 C nachgeruehrt und anschliessend mit 500 ml 20%-iger waessriger Ammoniumchloridloesung versetzt. Die Mischung wird mit tert.-Butylmethylether (2x 400 ml) extrahiert und die organischen Phasen nacheinander mit 0,1 M Natriumthiosulfatloesung (1x 500 ml), Wasser (1x 500 ml) und Sole (1x 500 ml) gewaschen. Die vereinigten organischen Phasen werden mit 150 g Natriumsulfat getrocknet und eingedampft. Aus dem Rueckstand wird mittels Destillation die Titelverbindung A1 als farbloses Oel erhalten (86,1 g, 84 %). 1H-NMR (400 MHz, CDCl3, delta) : 0,95 (m, 6H), 1,30 (t, 3H), 1,92 (m, 1H), 2,20 – 2,40 (m, 3H), 4,20 (m, 2H), 5, 80 – 6,10 (m, 2H) ppm.

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; Speedel Pharma AG; EP1200384; (2004); B1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 6306-61-2, name is N-(2-Chloroethyl)propan-2-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 6306-61-2, Application In Synthesis of N-(2-Chloroethyl)propan-2-amine hydrochloride

To a stirred mixture of 2-methyltetrahydrofuran (1.5L) and KOH (140g, 250mmol) was added water (30ml_). Then intermediate 3 (60g, 166mmol)) andtetrabutylammoniumbromide (13.4g, 41 mmol) were added and the mixture was heated at 50C for 1 hour while stirring. Then N-(2-chloroethyl)-2-propanamine HCI (CAS[6306- 61 -2]) (48g, 299mmol) was added in 1 portion. The mixture was stirred for 18 hours at 50C. When the conversion was complete, water (600ml_) was added to the reaction mixture. The layers were separated and the organic layer was concentrated. The residue was dissolved in 2-propanol (120ml_) and HCI in 2-propanol was added at 60C. After cooling, the HCI-salt was isolated via filtration. After drying at 50C in a vacuum drying oven the HCI-salt was obtained in 83% yield (compound 4a).

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, N-(2-Chloroethyl)propan-2-amine hydrochloride, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ASTEX THERAPEUTICS LIMITED; SAXTY, Gordon; MURRAY, Christopher William; BERDINI, Valerio; BESONG, Gilbert Ebai; HAMLETT, Christopher Charles Frederick; JOHNSON, Christopher Norbert; WOODHEAD, Steven John; READER, Michael; REES, David Charles; MEVELLEC, Laurence Anne; ANGIBAUD, Patrick Rene; FREYNE, Eddy Jean Edgard; GOVAERTS, Tom Cornelis Hortense; WEERTS, Johan Erwin Edmond; PERERA, Timothy Pietro Suren; GILISSEN, Ronaldus Arnodus Hendrika Joseph; WROBLOWSKI, Berthold; LACRAMPE, Jean Fernand Armand; PAPANIKOS, Alexandra; QUEROLLE, Oliver Alexis Georges; PASQUIER, Elisabeth Therese Jeanne; PILATTE, Isabelle Noelle Constance; BONNET, Pascal Ghislain Andre; EMBRECHTS, Werner Constant Johan; AKKARI, Rhalid; MEERPOEL, Lieven; WO2011/135376; (2011); 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. 69411-05-8, name is 3-Chloro-5-trifluoromethylaniline belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Product Details of 69411-05-8

Intermediate B (200 mg, 0.41 mmol), 3-chloro-5-(trifluoromethyl)benzenamine (80 mg, 0.41 mmol) and DIEA (106 mg, 2 mmol) were dissolved in THF (20 ml_). The reaction mixture was heated to 85C for 18 hours. The solvent was removed under reduced pressure and the crude product was purified by column chromatography on silica gel (eluent DCM:methanol 100. to 98:2) to followed by pre-HPLC to give the titled compound (14 mg, 5.8%) as a white solid. LCMS (method B): 2.66 min [MH]+=592.2. 1H NMR (400 MHz, DMSO-d6) delta ppm 3.45 (s, 3 H) 5.81(d, J= 6.4 Hz, 1 H) 7.30 (m, 4 H) 7.43 (m, 3 H) 7.61 (d, J=8.8, 2 H) 7.90 (m, 4 H) 8.55 (s, 1 H) 9.18 (s, 1 H) 9.39 (s, 1 H) 9.57 (s, 1 H).

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

Reference:
Patent; CATALYST THERAPEUTICS PTY LTD; LESSENE, Guillaume Laurent; GARNIER, Jean-Marc; CUZZUPE, Anthony Nicholas; FEUTRILL, John Thomas; CZABOTAR, Peter Edward; SHARMA, Pooja; (142 pag.)WO2016/127213; (2016); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Application of 95-81-8, 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. 95-81-8, name is 2-Chloro-5-methylaniline belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Reference Example 6 4-(4-Hydroxyanilino)-6-(2-chloro-5-methylanilino)pyrimidine The title compound was prepared in a similar manner to that of Reference Example 4 from 4-(4-hydroxyanilino)-6-chloropyrimidine (Reference Example 5) by reaction with 2-chloro-5-methylaniline in butan-1-ol in the presence of catalytic concentrated hydrochloric acid. The mixture was heated at reflux for 18 hours, concentrated and the residue purified by column chromatography eluding with DCMN:MeOH: concentrated ammonia (94:5:1). Yield 84%. NMR: 2.26 (3H, s), 5.85 (1H, s), 6.68 (2H, d), 6.93 (1H, d), 7.19 (2H, d), 7.32 (1H, d), 7.46 (1H, s), 8.09 (1H, s), 8.44 (1H, s), 8.69 (1H, s), 9.11 (1H, s); m/z 327 (MH+).

The synthetic route of 2-Chloro-5-methylaniline has been constantly updated, and we look forward to future research findings.

Reference:
Patent; AstraZeneca AB; US6632820; (2003); B1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Electric Literature of 367-22-6,Some common heterocyclic compound, 367-22-6, name is 4-Chloro-3-fluoroaniline, molecular formula is C6H5ClFN, 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 suspension of 4-chloro-3-fluoroaniline (10.67 g, 73.3 mmol) and Na2CO3 (24.5 g, 125 mmol) in Et20 (300 ml) at -10 C under N2 was added TFAA (12.23 ml, 88 mmol) dropwise. The mixture was allowed to warm to rt for 18 h. The reaction mixturewas diluted with hexane (300 ml), and filtered. The filtrate was washed with ice-water,10% aq NaHCO3, and brine, dried over Na2SO4, and concentrated. A pale yellow solid obtained as N-(4-chloro-3-fluorophenyl)-2,2,2-trifluoroacetamide (17 g, 96 % yield). MS (ESI) m/z: 242.1 (M+H)t

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-3-fluoroaniline, its application will become more common.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; SMITH II, Leon M.; PINTO, Donald J. P.; CORTE, James R.; EWING, William R.; (163 pag.)WO2016/205482; (2016); A1;,
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. 348-59-4, name is 2,5-Dichlorofluorobenzene, A new synthetic method of this compound is introduced below., Recommanded Product: 348-59-4

[ETHYL 4-[(4-HYDROXY-1-PIPERIDINYL)METHYL]-?-PHENYL-1-PIPERIDINEACETATE ] (0.135 g) was dissolved in NMP (3 mL). 1, 4-Dichloro-2-fluorobenzene (0.2 mL) and potassium t- butoxide (56 mg) were added and the solution was heated to [50 C] for 40 h. The solution was cooled to ambient temperature and few drops of aqueous sodium hydroxide solution were added. The mixture was stirred for 60 h, then acetic acid (few drops) was added and the solvent was distilled. The residue was purified by HPLC (0.2% aqueous ammonia: acetonitrile; gradient 95: 5 to 50: 50) to give the title compound (21 mg). MS [[M+H] +] (ES+) 477/479 [IH] NMR [8 (CD30D)] 1.45 (1H, q), 1.68-1. 96 (9H, m), 2.16-2. 21 (2H, m), 2.25-2. 34 (2H, m), 2.57-2. 65 (3H, m), 2.80-2. 93 (2H, m), 4.29-4. 36 [(1H,] m), 4.38-4. 44 [(1H,] m), 6.83 [(1H,] dd), 7.02 (1H, d), 7.23 (1H, d), 7.32-7. 36 (3H, m), 7.44-7. 49 (2H, m)

The synthetic route of 348-59-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ASTRAZENECA AB; WO2004/29041; (2004); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Related Products of 698-01-1, 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. 698-01-1 name is 2-Chloro-N,N-dimethylaniline, 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.

General procedure: A mixture of benzoyl chloride 1a (0.5 mmol), N,N-dimethylaniline 2a (1.5 mmol), KMnO4 (1.5 equiv.) and CH3CN (2.0 mL) was placed in a 25 mL reaction straight tube under air atmosphere. The tube was then placed in an oil bath, stirred and heated at 60 C for 6 h. After cooling to room temperature, the system was flushed to Sand core funnel using dichloroethane (rinsing three times, VDCM < 50 mL), Vacuum filtration, and the volatile solvent was removed in vacuo. The crude product was purified through a silica gel column (ethyl acetate/petroleum ether = 1:5) to afford (93%) a yellow liquid. At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-Chloro-N,N-dimethylaniline, and friends who are interested can also refer to it. Reference:
Article; Zhang, Zhang; Liu, Yong-Hong; Zhang, Xi; Wang, Xi-Cun; Tetrahedron; vol. 75; 19; (2019); p. 2763 – 2770;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Reference of 918538-05-3, 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. 918538-05-3, name is 2,4-Dichloropyrrolo[2,1-f][1,2,4]triazine belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

General procedure: Compound 183a was prepared from tert-butyl 2,4-dichloro-5,6-dihydropyrido[3,4- d]pyrimidine-7(8H)-carboxylate (182a) (1.0 g, 3.29 mmol) in 2-Propanol (15 mL) using DIPEA (2.3 mL, 13.15 mmol) and 1-(3,4,5-trimethoxyphenyl)-1H-imidazol-4-amine (57a) (0.98 g, 3.95 mmol). This gave after workup and purification by flash column chromatography [silica gel, (12 g) eluting with DMA-80 in DCM (0 to 80%)] fert-butyl 2-chloro-4-((l-(3,4,5- trimethoxyphenyl)-lH-imidazol-4-yl)amino)-5,6-dihydropyrido[3,4-d]pyrimidine-7(8H)- carboxylate (183a) (0.87 g, 51 % yield) as a buff solid; NMR (300 MHz, DMSO-^e) delta 9.65 (s, 1H, D20 exchangeable), 8.16 (d, J = 1.5 Hz, 1H), 7.78 (d, J = 1.6 Hz, 1H), 6.90 (s, 2H), 4.35 (s, 2H), 3.87 (s, 6H), 3.69 (s, 3H), 3.61 (t, J = 5.8 Hz, 2H), 2.69 – 2.60 (m, 2H), 1.43 (s, 9H).

The synthetic route of 2,4-Dichloropyrrolo[2,1-f][1,2,4]triazine has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BIOCRYST PHARMACEUTICALS, INC.; KOTIAN, Pravin, L.; BABU, Yarlagadda, S.; KUMAR, V., Satish; ZHANG, Weihe; LU, Peng-Cheng; RAMAN, Krishnan; (747 pag.)WO2018/232094; (2018); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Some common heterocyclic compound, 1005-56-7, name is O-Phenyl carbonochloridothioate, molecular formula is C7H5ClOS, 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. Product Details of 1005-56-7

6a (100 mg, 0.30 mmol) was dissolved in 5 mL of acetonitrile,4-Dimethylaminopyridine (162 mg,1.33 mmol) andPhenylchloroformate (0.1 mL)After stirring at 0-60 C for 2-12 hours, the reaction solution was filtered, concentrated and separated by column(N-hexane / ethyl acetate: 20/1) gave a colorless oil 8 (128 mg, 0.27 mmol, 90%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1005-56-7, its application will become more common.

Reference:
Patent; China Pharmaceutical University; Xie Weijia; Zhang Chenxi; Wang Zihao; Wu Xiaoming; Xu Jinyi; Yao Hequan; Lin Aijun; (12 pag.)CN107043403; (2017); A;,
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. 95-81-8, name is 2-Chloro-5-methylaniline, A new synthetic method of this compound is introduced below., COA of Formula: C7H8ClN

(A-82-21) tert-Butyl 4-(2-chloro-5-methylphenylcarbamoyl)-3-[4-cyclopropyl-5-(3-isobutylcyclobutyl)isoxazol-3-yl]butanoate Mono-tert-butyl 3-[4-cyclopropyl-5-(3-isobutylcyclobutyl)isoxazol-3-yl]glutarate (2.83 g) and DMF (28 mL) were mixed. After an addition of 2-chloro-5-methylphenylamine (1.184 g), HOBt.H2O (1.28 g) and WSC.HCl (1.60 g) to the resultant solution, the mixture was stirred at RT for 2 days. To the reaction mixture was added saturated aqueous sodium bicarbonate, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium bicarbonate, water and brine, then dried over sodium sulfate. The sodium sulfate was filtered off and the filtrate was concentrated in vacuo. The resultant residue was purified by silica gel column chromatography (Eluent: ethyl acetate/hexane=1/15?1/10?1/8) to give the title compound (1.241 g).

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

Reference:
Patent; JAPAN TOBACCO INC.; US2012/322837; (2012); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics