Tag: M.W=100-200

Some common heterocyclic compound, 10061-02-6, name is trans-1,3-Dichloropropene, molecular formula is C3H4Cl2, 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 trans-1,3-Dichloropropene

To a solution of i-Pr2NH (7.06 mL, 50.4 mmol, dried over CaH2) in dry THF (50 mL) cooled at -78 C under N2 was added n-BuLi (24.6 mL, 49.2 mmol, 2.0 M) dropwise. The resultant solution was allowed to warm to 0 C followed by stirring for 1 h at the same temperature to form a yellow solution of lithium diisopropylamide (LDA).To the above prepared LDA solution cooled at -78 C, was added slowly methyl acetoacetate (2.59 mL, 24 mmol) followed by stirring at 0 C for 1 h. To the resultant solution cooled at -78 C was added a solution of (E)-1,3-dichloropropene (1.85 mL, 20 mmol) in dry THF (10 mL) using a syringe followed by stirring for 10 min at the same temperature. The reaction was allowed to warm to 0 C; after stirringat 0 C for 16 h and at room temperature for another 2 h, the reaction was quenched by addition of H2O (50 mL). The reaction mixture was extracted with EtOAc (50 mL x 3). The combined organic layer was washed with brine (50 mL) and dried over anhydrous Na2SO4, filtered, and concentrated under reduced pressure. The residue was purified by flash column chromatography over silica gel (17% EtOAc in hexane) to afford the product 44 (3.31 g, 87%) as a colorless oil. IR (film): 2955, 2929, 1747, 1717, 1633,1438, 1323, 1261 cm1; 1H NMR (400 MHz, CDCl3) d 5.96 (d,J 13.2 Hz, 1H), 5.82 (dt, J 13.2, 7.2 Hz, 1H), 3.68 (s, 3H), 3.41 (s,2H), 2.61 (t, J 7.2 Hz, 2H), 2.30 (dt, J 7.2, 7.2 Hz, 2H); 13C NMR(100 MHz, CDCl3) d 201.2, 167.4, 131.7, 118.4, 52.5, 49.0, 41.8, 24.6;HRMS (CI) calcd for C8H12ClO3 191.0475 (MH), found 191.0470 and C8H1237ClO3 193.0445 (MH), found 193.0448.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 10061-02-6, its application will become more common.

Reference:
Article; Su, Ye-Xiang; Dai, Wei-Min; Tetrahedron; vol. 74; 13; (2018); p. 1546 – 1554;,
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, Formula: C5H13Cl2N

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

Related Products of 67952-93-6,Some common heterocyclic compound, 67952-93-6, name is 3-Chloro-4-methylbenzylamine, molecular formula is C8H10ClN, 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.

1,4-Dichlorophthalazine-6-carbonitrile and 3-chloro-4-methylbenzylamine were stirred at room temperature in 1-methyl-2-pyrrolidinone in the presence of DBU, whereby the title compound was obtained as a less polar compound. 1H-NMR (400 MHz, DMSO-d6) delta; 2.29 (3H, s), 4.73 (2H, d, J=5.2 Hz), 7.28-7.32 (2H, m), 7.45 (1H, d, J=0.8 Hz), 8.20 (1H, dd, J=8.4, 0.4 Hz), 8.34 (1H, d, J=8.4, 1.6 Hz), 8.52 (1H, t, J=5.2 Hz), 9.00 (1H, m).

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-4-methylbenzylamine, its application will become more common.

Reference:
Patent; Eisai Co., Ltd.; US6498159; (2002); B1;,
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. 13726-14-2, name is 4-Chloro-3-methoxyaniline, A new synthetic method of this compound is introduced below., Computed Properties of C7H8ClNO

Step 1(4-Chloro-3-methoxy-phenyl)-methyl-amineIn a 50 mL flask are added 4-Chloro-3-methoxy-phenylamine (907 mg), sodium methoxide (1.56 g), 10 mL anhydrous methanol, and paraformaldehyde (690 mg). Reaction mixture is then stirred overnight at room temperature. Then, paraformaldehyde (173 mg) and sodium methoxyde (311 mg) are added, and reaction mixture is heated at reflux for 1 hour. Sodium borohydride (436 mg) is then added, and reaction mixture is stirred at reflux for 4 hours. Once back at room temperature, mixture is partially evaporated, and KOH aq 1M (50 mL) is then added. The obtained suspension is extracted by Et20, organic phase is dried over Na2S04 and evaporated. The obtained residue is purified by flash chromatography (cHex to cHex/EtOAc 8/2) to give 650 mg of the expected product (66 %).MS [M+H]+ m/z = 171.9 1H-NMR (DMSO- 6) : delta (ppm) 2.66 (d, J = 4.9 Hz, 3H) ; 3.77 (s, 3H) ; 5.80 (q, J = 4.9 Hz, 1H) ; 6.09 (dd, J = 2.5 Hz, J = 8.7 Hz, 1H) ; 6.25 (d, J = 2.4 Hz, 1H) ; 7.04 (d, J = 8.7 Hz, 1H).

The synthetic route of 13726-14-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; UNIVERSITE DE LILLE 2 DROIT ET SANTE; INSTITUT PASTEUR DE LILLE; INSERM (INSTITUT NATIONAL DE LA SANTE ET DE LA RECHERCHE MEDICALE); CHARTON, Julie; DEPREZ, Benoit; LEROUX, Florence; STAELS, Bart; MUHR-TAILLEUX, Anne; HENNUYER, Nathalie; LESTAVEL, Sophie; LASSALLE, Manuel; DUBANCHET, Barbara; WO2015/189330; (2015); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

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

Synthetic Route of 94-97-3, 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. 94-97-3 name is 5-Chloro-1H-benzo[d][1,2,3]triazole, 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.

A solution of 5-chloro-1/-/-benzotriazole (1 53 g) in THF was added at 0C to a mixture of diisopropylic azodicarboxylate (2 ml_), triphenyl phosphine (2.9 g) and allyl alcohol (1.4 mL) in THF. After stirring one hour at 00C, the mixture was concentrated under reduced pressure to give a residue that was purified by chromatography (SiO2, heptane/EA) to afford 2-allyl-5-chloro-2/-/-benzotriazole (1.02 g, 53%). A mixture of 1- allyl-5-chloro-1/-/-benzotriazole and 1-allyl-6-chloro-1/-/-benzotriazole was also recovered (0.9 g, 47%). Alternatively, 2-allyl-5-chloro-2H-benzotriazole [4.87 g, 25%,Rf =0.4 (1 :3 EA/heptane)] was obtained using a procedure similar to that described in Example 1 , part a, except using 3-bromopropene. Similarly, a mixture of 1-allyl-5- chloro-1 H-benzotriazole and 1-allyl-6-chloro-1/-/-benzotriazole was also recovered [10.81 g, 56%, Rf =0.2 (1 :3 EA/heptane)]

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 5-Chloro-1H-benzo[d][1,2,3]triazole, and friends who are interested can also refer to it.

Reference:
Patent; MERIAL LIMITED; AVENTIS AGRICULTURE; WO2008/144275; (2008); 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. 7149-75-9, name is 4-Chloro-3-methylaniline, A new synthetic method of this compound is introduced below., HPLC of Formula: C7H8ClN

General procedure: To a solution of ethyl acetoacetate (10 mmol) in 40 mL of toluene was added appropriate amine(10 mmol) and a catalytic amount of potassium tert-butoxide. The resulting mixture was heated torefluxing for 6 hours. After the reaction mixture was cooled to room temperature, the solvent wasremoved under rotovap and the crude product was purified by flash chromatography on silica gelusing hexane:EtOAc (1:1) to afford desired products as colorless crystalline solid (40%-63%).

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; Tang, Jing; Huber, Andrew D.; Pineda, Dallas L.; Boschert, Kelsey N.; Wolf, Jennifer J.; Kankanala, Jayakanth; Xie, Jiashu; Sarafianos, Stefan G.; Wang, Zhengqiang; European Journal of Medicinal Chemistry; vol. 164; (2019); p. 179 – 192;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 15205-11-5, name is 2-Chloro-4-fluorobenzylamine, 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 15205-11-5, Recommanded Product: 2-Chloro-4-fluorobenzylamine

Example 1; lambda/-[(2-chloro-4-fluorophenyl)methyl]-2-(1 ,4-dimethyl-1 H-pyrazol-5- yl)acetamide (E1); A mixture of (1 ,4-dimethyl-1 H-pyrazol-5-yl)acetic acid and (1 ,4-dimethyl-1H-pyrazol- 3-yl)acetic acid (1.2 g, 2.mmol, prepared as described below), 1- hydroxybenzotriazole hydrate (324 mg, 2.4 mmol), 1-ethyl-3-(3- dimethylaminopropyl)carbodiimide hydrochloride (460 mg, 2.4 mmol) and lambda/-ethyl morpholine (690 mg, 0.76 ml, 6 mmol) in dichloromethane (10 ml) was stirred at room temperature for 10 minutes. A solution of [(2-chloro-4- difluorophenyl)methyl]amine (319 mg, 2 mmol) in dichloromethane (1 ml) was added and the reaction stirred at room temperature for 4 hours. The reaction mixture was diluted with saturated sodium bicarbonate solution and dichloromethane. The organic layer was separated washed with water and brine, dried and evaporated. The residue was purified by column chromatography on silica gel eluting with ethyl acetate/hexane mixtures (1 :1 to neat ethyl acetate), followed by silica gel chromatography eluting with dichloromethane/methanol (40:1 ) to give lambda/-[(2-chloro-4- fluorophenyl)methyl]-2-(1 ,4-dimethyl-1 H-pyrazol-5-yl)acetamide.LC/MS [M+H]+ = 329, retention time = 2.35 minutes.

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-4-fluorobenzylamine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; GLAXO GROUP LIMITED; WO2008/125600; (2008); A2;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 1005-56-7, name is O-Phenyl carbonochloridothioate, 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 1005-56-7, Computed Properties of C7H5ClOS

General procedure: 1a (0.996g, 1.5mmol) / 1b (0.204g, 0.30mmol), NaOH (0.18g, 4.5mmol / 0.072g, 1.8mmol) in 20mL Stir in CH2Cl2 for 15 minutes. Join slowly in 5 minutesPhenyl thiochloroformate(0.258 g, 1.5 mmol / 0.103 g, 0.6 mmol).The TLC dot plate tracks the progress of the reaction and stops the reaction after the disappearance of the raw materials.10% HCl was added to the reaction solution to neutralize excess NaOH.After oscillating, the organic phase was separated and the aqueous phase was extracted with CH2Cl2.The organic phase was combined, washed with brine and dried over anhydrous sodium sulfate.After concentrating by evaporation, the crude product was purified and purified by ethylamine (ethyl acetate: petroleum ether = 1:100) to give white solid 2a (0.75 g, yield 71%) and 2b (0.171 g,Yield 75%).

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; Changzhou University; Li Zhengyi; Tong Hongxiao; Chen Yuan; Yin Le; Xiao Tangxin; Sun Xiaoqiang; (9 pag.)CN108727241; (2018); A;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Reference of 15205-11-5, A common heterocyclic compound, 15205-11-5, name is 2-Chloro-4-fluorobenzylamine, molecular formula is C7H7ClFN, 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 3 N-[(2-chloro-4-fluorophenyl)methyl]-1-ethyl-5-oxo-prolinamide (E3) Methyl 1-ethyl-5-oxo-prolinate (0.135 g, 0.79 mmol, prepared as described below) was dissolved in methanol (4 ml) and treated with 2M aqueous sodium hydroxide (0.592 ml, 1.18 mmol). The mixture was stirred for 4 hrs at room temperature and then evaporated to give a residue which was then treated with an excess of 1M hydrogen chloride in ether (~5 ml) for 10 minutes. The mixture was evaporated once more and the residue was dissolved in dichloromethane (4 ml) and dimethylformamide (2 ml) and filtered to remove solids. The resulting solution was transferred to a reaction tube and 1-hydroxybenzotriazole (0.117 g, 0.87 mmol), [(2-chloro-4-fluorophenyl)methyl]amine (0.138 g, 0.87 mmol) and N-(3-dimethylaminopropyl)-N’-ethylcarbodiimide hydrochloride (0.167 g, 0.87 mmol) were then added. The mixture was flushed with argon and then stirred at room temperature over the weekend. The mixture was then diluted with dichloromethane and washed sequentially with 2M aqueous hydrogen chloride and saturated aqueous sodium hydrogen carbonate. The organic layer was filtered through a phase separator and then evaporated to give the crude product. The crude material was purified by mass-directed automated HPLC to give pure N-[(2-chloro-4-fluorophenyl)methyl]-1-ethyl-5-oxo-prolinamide (0.086 g) as a white solid. LC/MS [M+H]+=299.1, retention time=2.13 minutes. Enantiomeric excess=100.0%, as determined by chiral chromatography method B, indicative of N-[(2-chloro-4-fluorophenyl)methyl]-1-ethyl-5-oxo-L-prolinamide retention time=8.05 minutes

The synthetic route of 15205-11-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXO GROUP LIMITED; US2008/9541; (2008); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics