Tag: M.W=100-200

Adding a certain compound to certain chemical reactions, such as: 918538-05-3, name is 2,4-Dichloropyrrolo[2,1-f][1,2,4]triazine, 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 918538-05-3, name: 2,4-Dichloropyrrolo[2,1-f][1,2,4]triazine

General procedure: To a solution of 2,4-dichlorofuro[3,2-d]pyrimidine (la) (0.71 g, 3.74 mmol; CAS 956034- 07-4) in 2-Propanol (20 mL) was added DIPEA (1.63 mL, 9.36 mmol), 1-methyl-1H-imidazol-4-amine hydrochloride (0.5 g, 3.74 mmol) and heated at reflux for 24 h. The reaction mixture was concentrated in vacuum to dryness and the residue obtained was triturated with water. The solid obtained was collected by filtration and dried in vacuum to afford 2-chloro-N-(l-methyl-lH-imidazol-4-yl)furo[3,2-d]pyrimidin-4-amine (lb) (550 mg,59 % yield) as brown solid; NMR (300 MHz, DMSO-^) delta 10.89 (s, 1H, D20exchangeable), 8.35 (d, J = 2.1 Hz, 1H), 7.52 (d, J = 1.6 Hz, 1H), 7.39 (d, J = 1.3 Hz, 1H), 7.03 (d, J = 2.1 Hz, 1H), 3.71 (s, 3H); MS (ES+): 250.3 (M+l), 272.3, 274.3 (M+Na), (ES-): 248.2 (M-l).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2,4-Dichloropyrrolo[2,1-f][1,2,4]triazine, and friends who are interested can also refer to it.

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

Reference of 22680-44-0, These common heterocyclic compound, 22680-44-0, name is (2-Chlorophenyl)methanamine hydrochloride, 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.

(ii) 1-(2-chlorophenyl)methyl-2-propyl-2-thiopseudourea A solution of 2-chlorobenzylamine hydrochloride (41 g, 0.23 mol) and ammonium thiocyanate (19.28 g, 0.253 mol) in water (170 mL) was heated on the steam bath for 18 hours. This mixture was concentrated in vacuo, and the residue was taken up in toluene (1 L) and azeotroped with a Dean-Stark head. The residue was triturated with wet diethyl ether to provide 27.6 g (60%) of 1-(2-chlorophenyl)methyl thiourea. The product was recrystallized from ethanol; mp 120-122 C. A mixture of 1-(2-chlorophenyl)methyl thiourea (3 g, 14.9 mmol) and propylbromide (13.5 g, 110 mmol) in acetonitrile (20 mL) was refluxed for 5 hours. The solvent was evaporated, the residue was dissolved in 200 mL of 50% water/ether and acidified with 48% hydrobromic acid solution. The two phases were separated, the aqueous layer was washed with ether and then the aqueous layer was basified with 10% sodium carbonate solution. The liberated product was extracted with diethyl ether, washed with water and brine, dried and concentrated to give 1-(2-chlorophenyl)methyl-2-propyl-2-thiopseudourea (2.82 g, 78%); mp 112-114 C.

The synthetic route of 22680-44-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SmithKline Beecham Corporation; US5444080; (1995); A;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Related Products 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 suspension of sodium hydride (purity >55%, 11.4 g)in N,N-dimethylformamide (150 mL), 3-chloro-2-chloromethyl-1-propene (12.7 mL)was added under ice-cooling, and the mixture was stirred at the same temperature for 10 minutes. Then, a solution of 2-(tert-butoxycarbonylamino)-1-ethanol (19.3 g)in tetrahydrofuran (150 mL)was added dropwise over 1.5 hours, and the mixture was stirred at room temperature for 2.5 hours. The reaction solution was cooled with ice, then water was added, and then the mixture was extracted with diethyl ether three times. The organic layer was washed with saturated brine, then dried over anhydrous sodium sulfate. The resultant was filtered, and concentrated under reduced pressure, then the residue obtained was purified by silica gel column chromatography (hexane/ethyl acetate)to obtain the title compound (16.0 g)as an oil. 1H-NMR (CDCl3)delta: 5.06-4.95 (2H, m), 4.19-4.06 (4H, m), 3.76-3.69 (2H, m), 3.54-3.48 (2H, m), 1.46 (9H, s). MS (m/z): 114 (M-CO2tBu+H)+.

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; Daiichi Sankyo Co., Ltd.; NAITO, Hiroyuki; KAGOSHIMA, Yoshiko; FUNAMI, Hideaki; NAKAMURA, Akifumi; ASANO, Masayoshi; HARUTA, Makoto; SUZUKI, Takashi; WATANABE, Jun; KANADA, Ryutaro; HIGUCHI, Saito; ITO, Kentaro; EGAMI, Akiko; KOBAYASHI, Katsuhiro; EP3643703; (2020); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Some common heterocyclic compound, 1435-48-9, name is 2,4-Dichloro-1-fluorobenzene, molecular formula is C6H3Cl2F, 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 1435-48-9

In a 10001111 four-necked flask, 2,4-dichlorofluorobenzene was charged15 (^ (0.911111), cooling to 20 (: adding aluminum chloride 200. 2g (l.5mol), in the 20 ~ 30 CAdd acetyl chloride 78. 5g (l. Omol), 2 ~ 3h plus finished.Slowly heat up to 40 C and incubate for 30 min, then slowly heat up to 70 C and incubate for 1 ~ 2h, then slowly heat up to 110 C, 110 ± 2 CHeat 3 ~ 4h, cooling, add 500g 5% hydrochloric acid, hydrolysis at 80 ~ 90 C 2 ~ 3h, after washing to neutral, there areThe phase of the product was recrystallized from the second distillation to obtain 168 g of 2,4-dichloro-5-fluoroacetophenone in an amount of 99.8%. The yield was 89.3%

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1435-48-9, its application will become more common.

Reference:
Patent; Binhai Yongtai Medical Chemical Co Ltd; He, Renbao; Shao, Hongming; (8 pag.)CN102249881; (2016); B;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Synthetic Route of 501-29-1, These common heterocyclic compound, 501-29-1, name is 1-Chloro-2-fluoro-4-methoxybenzene, 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.

Tetrahydrofuran (8.35 L) into a 3-L four-neck flask equipped with a mechanical stirrer, an addition funnel and a temperature probe under N2 atmosphere. Charged 4-Chloro-3-fluoroanisole (1000 g) to a 3-L four-neck flask equipped with a mechanical stirrer, an addition funnel and a temperature probe. Cooled the reaction mass to -60 C. to -70 C. Added n-Butyl Lithium in hexanes (30%, 1.42 kg) in to reaction mass through canula under nitrogen atmosphere slowly, while maintaining the temperature of the reaction mass below -60 C. Maintained the reaction at below -60 C. for 2 h. Meanwhile Iodine solution prepared by dissolving Iodine (2.405 kg) in Tetrahydrofuran (2.4 L) at 25-28 C. Transferred the Iodine solution in step 6 into a clean addition funnel with THF (500 mL) rinse. Added Iodine solution from the addition funnel to the reaction over 120 min while maintaining the internal temperature at <-60 C. Removed cooling bath and allowed to attain -5 C. to 0 C. Submitted the IPC sample when it reaches -5 C. to 0 C.1. A sample was removed at -2 h and checked by HPLC-97.06 AP; Int-01-0.59 AP. Work Up: Quenched the reaction with 20% Na2SO2O3 solution (1.015 kg of sodium thiosulphate dissolved in 5.1 L of DM water) while maintaining the internal temperature at <10 C. Allowed RM to warm to RT. Transfer resulting biphasic mixture into separating funnel, rinse the flask with THF (1.2 L; 1.0-1.5 Vol wrt Int-1), and transfer to separating flask. Removed and retain bottom aqueous phase for further extraction. Concentrated the organic layer. Dissolved concentrated mass in EtOAc (8.0 L; 8.0-8.5 Vol wrt Int-1) Extract the retained aqueous phase with EtOAc (7.1 L: 7.0-7.5 Vol wrt Int-1). Combined all organic phases, Rinse the flask with EtOAc (1.0 L; 1.0-1.5 Vol wrt Int-1). Washed organic phases with DM water (5.7 L; 5.0-6.0 Vol wrt Int-1). Concentrated the organic layer2 on rotovap at 45-50 C. completely. Purification: Added Acetonitrile (5.1 L; 5.0-5.5 vol wrt Int-01). Warmed to 55 C. to dissolve all solid. Rotate the above mass in rotavapor flask at 55 C. for 10 min. Cooled to ambient temperature. Transferred the mass into a clean reactor, rinse the flask with Acetonitrile (1.0 L; 1.0-1.2 vol wrt Int 01) and add rinse into reactor. Added water (1 L; 1.0-1.2 vol wrt Int-01) in to reactor with stirring. Stirred the resulting slurry for 15 min. Added water (5.3 L; 5.0-5.5 Vol wrt Int-01) over 15 min. Stirred the above mass at ambient temperature for 15 min. Unload the mass into a container, rinsed the reactor with water (1 L; 1.0-1.2 vol wrt Int-01), and collected the rinse in same container. Filtered the solid. Rinsed the container with water (1 L; 1.0-1.2 vol wrt Int-01), filtered the rinse. Washed filter cake with water (3.3 L; 3.0-3.5 Vol wrt Int-01). Suck dried for 2 h, then dried at 55 C. in VTD for 15 h. Unload the material. (LOD should be less than 1%). Wt: 1533 g (85.9% yield). Description (color and appearance): Off White crystalline solid. HPLC RT Time 4.897 min Under following conditions: Detector: 210 nm; Injection volume 5.00 muL; Run Time 15 min; Column. YMC UltraHT Pro C18 (50 mm×3.0 mm), 2.0mu; Mobile Phase A-0.05% TFA in MillQ Water; Mobile Phase B-0.05% TFA in Acetonitrile; Flow: 1.0 mL/min; Column Oven-40 C.; Time (min)-0 05 10 12 15; B Conc.-10 90 90 10 10. NMR: (1H NMR, 400 MHz, dmso-d6) delta 7.58 (t, 8.8 Hz, 1H), 6.89 (m, 1H), 3.87 (s, 3H). The synthetic route of 501-29-1 has been constantly updated, and we look forward to future research findings. Reference:
Patent; Bristol-Myers Squibb Company; Yeung, Kap-Sun; Kadow, John F.; US2013/203775; (2013); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Synthetic Route of 14752-66-0, The chemical industry reduces the impact on the environment during synthesis 14752-66-0, name is Sodium 4-chlorobenzenesulfinate, I believe this compound will play a more active role in future production and life.

A mixture of 8-fluoro-3-iodoquinoline (750 mg, 2.75 mmol), sodium 4- chlorobenzenesulfinate (1.1 g, 5.5 mmol), copper (I) iodide ( 52 mg, 0.275 mmol) and potassium carbonate (380 mg, 2.75 mmol) was treated with lambda^, lambda^-dimethyl-l,2-ethanediamine (49 mg, 0.55 mmol) and anhydrous dimethylsulphoxide (4 ml). The mixture was stirred at 1000C under argon for 8 hr, and cooled to 200C. The reaction mixture was diluted with water (60 ml) and extracted with ethyl acetate (3 x 40 ml). The organic extracts were combined, washed with water (60 ml) and brine (60 ml), dried over magnesium sulphate, and evaporated to dryness. The residue was dissolved in a 1 :1 mixture of dimethylsulphoxide and acetonitrile and purified by mass-directed auto -preparative chromatography using 10 minute gradients containing water and between 50% and 99% acetonitrile with 0.1% formic acid. Product fractions were collected and evaporated to yield the title compound as a white solid (295 mg,deltaH (CDCl3, 400MHz) 7.51-7.69 (4H, m), 7.79 (IH, d, J = 8 Hz), 7.96-7.99 (2H, m), 8.84 (IH, d, J = 2 Hz), 9.30 (IH, d, J = 2 Hz)Mass spectrum: C15H9ClFNO2S requires 321; found 322 (MH+)

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

Reference:
Patent; GLAXO GROUP LIMITED; WO2008/116816; (2008); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Application of 363-51-9, 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. 363-51-9, name is 2-Chloro-6-fluoroaniline belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

To a solution of 2-chloro-6-fluorobenzenamine (5.0 g, 34 mmol) in chlorobenzene (52 mL) was added carbonothioic dichloride (thiophosgene) (5.1 g, 45 mmol) and DMF (0.27 mL). The reaction mixture was refluxed for 2 h and then concentrated to leave the title compound as a brown oil (6.15 g), which was used in Step C without further purification. ¾ NMR delta 7.18 (m, 2H), 7.07 (m, 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, 2-Chloro-6-fluoroaniline, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; E. I. DU PONT DE NEMOURS AND COMPANY; LONG, Jeffrey, Keith; GREGORY, Vann; GUTTERIDGE, Steven; TAGGI, Andrew, Edmund; BEREZNAK, James, Francis; WO2012/31061; (2012); A2;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

These common heterocyclic compound, 106131-61-7, name is 3,6-Dichloro-1,2,4,5-tetrazine, 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. category: chlorides-buliding-blocks

To a solution of 3, 6-dichloro- 1,2,4,5 -tetrazine (2.67 g, 17.7 mmol) in methyl ter/-butyl ether (125 mL) at -25 C under nitrogen was added but-3-yn-l -amine hydrochloride (1.87 g, 17.7 mmol), followed by the addition of N,N-diisopropylethylamine (12.4 mL, 70.7 mmol) and the reaction mixture was stirred at -25 C under nitrogen for 26 h. Silica gel (-5 g) was added to the reaction and all solvents were removed in vacuo. The silica gel mesh was loaded on an ISCO silica gel cartridge (220 g) eluting with 25% (0558) EtOAc/hexanes over 2592 mL to afford the title compound (853.3 mg) as a deep red/orange viscous oil,. NMR (400 MHz, CDCh) delta 6.12 (br s, 1H), 3.80 (q, J=6.3 Hz, 2H), 2.63 (td, J=6.3, 2.6 Hz, 2H), 2.10 (t, J=2.6 Hz, 1H).

The synthetic route of 3,6-Dichloro-1,2,4,5-tetrazine has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; BENDER, John A.; GENTLES, Robert G.; PENDRI, Annapurna; WANG, Alan Xiangdong; MEANWELL, Nicholas A.; BENO, Brett R.; FRIDELL, Robert A.; BELEMA, Makonen; NGUYEN, Van N.; YANG, Zhong; WANG, Gan; KUMARAVEL, Selvakumar; THANGATHIRUPATHY, Srinivasan; BORA, Rajesh Onkardas; HOLEHATTI, Shilpa Maheshwarappa; METTU, Mallikarjuna Rao; PANDA, Manoranjan; (319 pag.)WO2016/172424; (2016); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

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. 1435-44-5, name is 1-Chloro-2,4-difluorobenzene, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of 1-Chloro-2,4-difluorobenzene

(a) 3-Chloro-2,6-difluorobenzaldehyde n-Butyllithium (1.43M in hexane, 20.2 mmol, 14.1 ml) was added dropwise at 0 C. to a solution of diisopropylamine (2.91 ml, 22.2 mmol) in THF (80 ml). After 30 min. at 0 C., the solution was cooled to -78 C. and 1-chloro-2,4-difluorobenzene (3 g, 20.2 mmol) in THF (10 ml) added dropwise. After 30 min., 4-formylmorpholine (4.1 ml) was added and the mixture warmed to room temperature over 1 h, diluted with 1N HCl, extracted twice with ethyl acetate, the extracts washed with brine, dried over sodium sulphate and evaporated to give a mobile yellow oil (2.2 g), MS (+EI) 178/177/176/175 (M+), 1H NMR (CDCl3) 10.34 (1H, s), 7.66-7.60 (1H, m), 7.00 (1H, dt, J6.9 Hz, 1.2 Hz).

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 1435-44-5.

Reference:
Patent; Astra Pharmaceuticals Limited; US5883102; (1999); A;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

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. 10061-02-6, name is trans-1,3-Dichloropropene, This compound has unique chemical properties. The synthetic route is as follows., Formula: C3H4Cl2

To a 500 ml round bottom flask was charged 7-fluoro-6-nitrobenzoxazin-3-one (12.73 g, 0.060 mol) and potassium carbonate (9.95 g, 0.072 mol)Dissolved in 60 ml of N,N-dimethylformamide to form a suspension,Heating to 80 C,After the reaction was kept at this temperature for 30 minutes,(E)-1,3-dichloropropene (8.00 g, 0.072 mol) was added dropwise thereto.The reaction was maintained at 80 C for an additional 4 hours. After stopping the reaction,Cool naturally to room temperature and pour into 200 ml of water.After extraction with ethyl acetate (100 ml × 3), the combined organic phases were washed with saturated aqueous sodium chloride (50 ml × 3), dried over anhydrous magnesium sulfate Ester: petroleum ether = 1:3) 12.20 g of (E)-4-(3-chloroallyl)-7-fluoro-6-nitrobenzoxazin-3-one as a yellow solid, yield 71 %.

According to the analysis of related databases, 10061-02-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Shenyang Sinochem Pesticide Chemical Research And Development Co., Ltd.; Li Bin; Chen Lin; Cui Dongliang; Guo Zhengfeng; Ma Hongjuan; Lian Weixiang; (23 pag.)CN109836393; (2019); A;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics