Author: Jessica.F

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. name: 3-Phenylpropyl Chloride

General procedure: To a suspension of alkyl halide (1 mmol) and nucleophilic reagents(NaOAc or KSCN) (2 mmol) in water (5 mL), Fe3O4SiO2/DABCO(0.225 g) was added and the mixture was stirred at 90 C for the lengths of time shown in Table 1. After completion of the reaction as indicated by TLC [using n-hexane/ethyl acetate (5:1)], the reaction was allowed to cool to room temperature and the magnetic catalyst was concentrated on the side wall of the reaction vessel using an external magnet. The reaction mixture residue was poured into water (10 mL)and extracted with EtOAc (3 × 10 mL). The combined organic layers were dried over anhydrous Na2SO4, filtered and evaporated in vacuo to give the product in 74% to 91% isolated yields.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 104-52-9, its application will become more common.

Reference:
Article; Davarpanah, Jamal; Kiasat, Ali Reza; Catalysis Communications; vol. 42; (2013); p. 98 – 103;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 33786-89-9, name is 5-Chloro-m-phenylenediamine, 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 33786-89-9, Formula: C6H7ClN2

4-Chloro-6,7-dimethoxyquinazoline (200 mg, 0.89 mmol) and 5-amino-3-chloroaniline (253 mg, 1.78 mmol)were combined in isopropanol (3 mL) and heated to reflux for 16 hours under an atmosphere of dry nitrogen. After coolingto 20C the mixture was diluted with methanol (5 mL) and the resulting precipitate was filtered and dried, in vacuo, toafford 252 mg (77%) of (3-amino-5-chlorophenyl)-(6,7-dimethoxyquinazolin-4-yl)amine hydrochloride (mp. 298-301 C;LC-MS: 331 (MH+)). A portion of this product (175 mg, 0.476 mmol) was dissolved in 80% acetic acid/H2O (12 mL),cooled to 0C, and a solution of NaNO2 (36 mg, 0.516 mmol) in H2O (300 mL) was added. The solution was stirred for10 minutes at 0C and NaN3 (33 mg, 0.50 mmol) in H2O (300 mL) was added. The reaction mixture was allowed to warmto 20C and stirred 16 hours. The resulting precipitate was filtered and dissolved in 10% methanol in CHCl3 and thesolution was washed with saturated aqueous NaHCO3, and brine, dried over Na2SO4, filtered and concentrated in vacuoto yield 59 mg (35%) of the title product as a yellow solid; mp 205-206C.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 5-Chloro-m-phenylenediamine, and friends who are interested can also refer to it.

Reference:
Patent; Pfizer Products Inc.; OSI Pharmaceuticals, LLC; Schnur, Rodney Caughren; Arnold, Lee Daniel; (28 pag.)EP2163546; (2016); B1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Synthetic Route of 39989-43-0, A common heterocyclic compound, 39989-43-0, name is 3,5-Dichlorobenzylamine, molecular formula is C7H7Cl2N, 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 45 Synthesis of Compound 46 (S)-9-fluorenylmethyl 10-(3,5-dichlorobenzyl)-2,2-dimethyl-4,9,13,16-tetraoxo-3,17-dioxa-5,10,15-triazaiscos-19-en-8-ylcarbamate To 3,5-dichlorobenzylamine (0.49 g, 2.8 mmol) in DCM (5 mL) was added the alpha,beta-unsaturated ketone 45 (2.12 mmol) in DCM (10 mL). After stirring at room temperature for 15 mins, Fmoc-diaminobutyric acid(Boc)-OH (1.35 g, 3.1 mmol) and DIC (0.5 mL, 3.2 mmol) was added. The reaction was stirred at room temperature overnight. The DCM was removed by rotary evaporation and the residue was subjected to column chromatography on silica gel using petroleum ether:EtOAc (1:1 to 0:1), providing compound 46 (0.48 g, 22%).

The synthetic route of 39989-43-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Blaskovich, Mark Arnold Thomas; Cassidy, Peter Joseph; US2009/221557; (2009); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Synthetic Route of 74483-46-8,Some common heterocyclic compound, 74483-46-8, name is 2-Chloro-4-methyl-1-(trifluoromethyl)benzene, molecular formula is C8H6ClF3, 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.

Intermediate 4: 4-(Bromomethyl)-2-chloro-1-(trifluoromethyl)benzene; To a solution of 2-chloro-4-methyl-1-(trifluoromethyl)benzene (0.5g, 2.57 mmol) in dry carbone tetrachloride (5OmL), N-bromo succinimide (0.412g, 2.313mmol) and benzoyl peroxide (12mg, 0.05 mmol) were added. The reaction was stirred to reflux for 40 hours. After cooling at 00C, the reaction mixture was filtered and the solvent evaporated. The title compound was obtained (0.7g) and the crude compound was used in the next reaction without purification. GC/MS: m/z, 273 Rt: 5.5 min

The synthetic route of 74483-46-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SMITHKLINE BEECHAM CORPORATION; WO2009/16216; (2009); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Synthetic Route of 933190-51-3, These common heterocyclic compound, 933190-51-3, name is 8-Bromo-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.

General procedure: To a solution of 6a-6c (1 mmol) in THF (5 mL) was addedmorpholine (or (S)-3-methylmorpholine, or 8-oxa-3-azabicyclo[3.2.1]octane) (1.2 mmol) and Et3N (2.2 mmol). The mixture washeated under reflux for 12 h. The crude product was extracted with CH2Cl2, dried over Na2SO4, purified over silica gel chromatographyeluting with PE and EtOAc to give 7a-7g [43].

Statistics shows that 8-Bromo-6-chloroimidazo[1,2-b]pyridazine is playing an increasingly important role. we look forward to future research findings about 933190-51-3.

Reference:
Article; Mao, Beibei; Gao, Shanyun; Weng, Yiran; Zhang, Liangren; Zhang, Lihe; European Journal of Medicinal Chemistry; vol. 129; (2017); p. 135 – 150;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Electric Literature of 627-42-9, These common heterocyclic compound, 627-42-9, name is 2-Methoxyethyl 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.

An excess of n-BuLi (2.5 M in n-hexane; 1.0 mL, correct stoichiometric amount corresponding to 0.50 mL, 1.24 mmol) was added via cannula through a rubber septum to a flask containing N,N-bis(2-phosphinoethyl)methoxyethylamine (5′) (60 mg, 0.31 mmol) in freshly distilled THF (10 mL) at 0 C. The solution became dark (black-violet coloured). Still at 0 C., under stirring, 2-chloroethyl methylether (236 mg, 2.48 mmol) dissolved in distilled THF (5 mL) was added dropwise. The mixture was left to reach room temperature overnight becoming yellow-gold coloured. It was then reduced to one third of the initial volume by a gentle stream of dinitrogen. Distilled diethylether (20 mL) was added. The flask was cooled again with an ice bath and degassed water (5 mL) was added dropwise. Two phases were formed: the upper organic phase was yellow-gold coloured, whereas the aqueous phase was almost colourless. Degassed diethylether (20 mL) was added, and the mixture was transferred in a separatory funnel (previously fluxed with dinitrogen) via cannula to avoid the contact with the atmosphere. Always under a dinitrogen atmosphere the lower aqueous phase was recovered in another separatory funnel and treated with additional diethylether (2×10 mL). Then the aqueous phase was discharged and the combined ethereal phases were placed in a 100 mL round bottom flask containing anhydrous Na2SO4 (ca. 500 mg). The solid was filtered off under dinitrogen and washed with additional anhydrous diethylether (2×10 ml). The combined ethereal phases were concentrated under dinitrogen and then under vacuum (yield ca. 60%).1H NMR (CDCl3): delta(ppm)=3.57-3.47 (10H); 3.33 (s, 12H); 3.32 (s, 3H); 2.66 (m, 6H); 1.78 (t, 8H); 1.65 (m, 4H).13C NMR (CDCl3): delta(ppm)=71.02 (s); 70.39 (d); 58.86 (s); 52.48 (s); 52.52 (s); 50.83 (d); 27.96 (d); 24.75 (d).31P{1H} (CDCl3): delta(ppm)=-39.0.

The synthetic route of 627-42-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NIHON MED-PHYSICS CO., LTD.; US2010/160615; (2010); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Synthetic Route of 2687-12-9, 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. 2687-12-9, name is Cinnamyl chloride belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

General procedure: To a well-stirred solution of 6a-e (1 mmol) in 4 mL of dry DMF was added the suitable organic halides (5.0-6.0 mmol) followed by K2CO3 (5.0-8.0 mmol) and the reaction mixture was heated at 70-80 C with stirring until the reaction was completed. The progress of the reaction was checked by TLC, which showed the appearance of new spots with higher Rf value than the starting compound. After the completion of the reaction, water was added to it and extracted with dichloromethane, washed successively with water and brine and then dried over anhydrous Na2SO4. The residue after solvent evaporation in vacuo, was purified by silica gel column chromatography (10% EtOAc : hexane). cis-3-pentyl-1,4-diphenyl-3-phenylsulfonyl-beta-lactam 7d

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, Cinnamyl chloride, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Bhalla, Aman; Modi, Garima; Yadav, Pooja; Kumar, Pankaj; Bari; Hundal, Geeta; Tetrahedron Letters; vol. 61; 29; (2020);,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Electric Literature of 6276-54-6, 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. 6276-54-6, name is 3-Chloropropan-1-amine hydrochloride, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: 2-Chlorobenzylamine (14.2 g, 0.10 mol), 4-chlorobenzylamine (14.2 g, 0.10 mol), and2,4-dichlorobenzylamine (17.6 g, 0.10 mol) were each dissolved in water (100 cm3),together with phosphorous acid (16.5 g, 0.20 mol), and concentrated hydrochloric acid (d1.18) (100 cm3) was added. The mixture was heated under reflux on a water bath (100C)and formalin (37% aqueous formaldehyde) (0.20 mol) was added portionwise. After 1 hwater was removed by evaporation until crystals appeared. The solution was then cooledand the product was filtered off and recrystallized three times from water to give theproduct as a white crystalline solid, as follows.

The chemical industry reduces the impact on the environment during synthesis 3-Chloropropan-1-amine hydrochloride. I believe this compound will play a more active role in future production and life.

Reference:
Article; Hudson, Harry R.; Koroma, Sia N.; Ojo, Isaac A. O.; Phosphorus, Sulfur and Silicon and the Related Elements; vol. 190; 12; (2015); p. 2187 – 2193;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Related Products of 10061-02-6, These common heterocyclic compound, 10061-02-6, name is trans-1,3-Dichloropropene, 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.

Potassium hydroxide (32.2 g) and toluene (250 mL) were taken into a round bottom flask and stirred for about 10 minutes. Dimethylisopropyl malonate (50 g) and tetrabutylammonium bromide (10 g) were then added to it and again stirred for about 10 minutes, trans-lambda ,3-Dichloropropene (35 g) was added to the reaction mixture and maintained at about 30-35 C for about 4 hours. After the reaction was completed, the reaction mass was quenched with water (500 ml_) and stirred for about 10 minutes. The reaction mixture was extracted into toluene (250 ml_), and the toluene layer was washed with water and then evaporated under reduced pressure to afford 51 g (82% yield) of (£)-dimethyl 2- (3-chloroallyl)-2-isopropylmalonate as a dark brown viscous liquid. Purity by GC: 96.84%

Statistics shows that trans-1,3-Dichloropropene is playing an increasingly important role. we look forward to future research findings about 10061-02-6.

Reference:
Patent; DR. REDDY’S LABORATORIES LTD.; DR. REDDY’S LABORATORIES, INC.; KOLLA, Naveen Kumar; APPAYE, Kaliyaperumal Srinivasan; GANGULA, Srinivas; GOVINDAPUR, Rajeshwar Reddy; MANNE, Nagaraju; NIKUMBH, Satish Pandurang; NEELAM, Uday Kumar; JOSEPH, Suju Chuttippari; BADDAM, Sudhakar Reddy; KUNHIMON, Shyam Kumar Unniaranpurakkal; MOOVENDAN, Mohan; DAHANUKAR, Vilas; DONIPARTHI, Kiran Kumar; WO2012/21446; (2012); A2;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics