Category: chlorides-buliding-blocks

Application of 39226-96-5, A common heterocyclic compound, 39226-96-5, name is (2-Chloro-3-(trifluoromethyl)phenyl)methanamine, molecular formula is C8H7ClF3N, 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 59 N-{[2-Chloro-3-(trifluoromethyl)phenyl]methyl}-3-methyl-1-(1-methyl- 1 H-imidazol-2-yl)-2-oxo-4-imidazolidinecarboxamide (E59) (in a form obtainable or prepared from (4S)-2-oxo-3-{[(phenylmethyl)oxy]carbonyl}-4-imidazolidinecarboxylic acid); A solution of 3-methyl-1-(1-methyl-1 H-imidazol-2-yl)-2-oxo-4-imidazolidinecarboxylic acid (166 mg, 0.517 mmol) and N-ethyl morpholine (0.397 ml, 3.10 mmol) in dichloromethane (5 ml) was treated with 1-hydroxybenzotriazole hydrate (95 mg, 0.620 mmol) and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (99 mg, 0.517 mmol) and stirred at room temperature for 10 minutes. 1-[2-Chloro-3- (trifluoromethyl)phenyl]methanamine (108 mg, 0.517 mmol) was then added and the reaction stirred overnight at room temperature. The reaction mixture was diluted with dichloromethane and washed with saturated sodium hydrogen carbonate solution, water and brine, separated through a hydrophobic frit and the organic layer was reduced under vacuum. The residue was purified by mass-directed automated HPLC to give N-{[2-chloro-3-(trifluoromethyl)phenyl]methyl}-3-methyl-1-(1-methyl-1 H- imidazol-2-yl)-2-oxo-4-imidazolidinecarboxamide (67 mg, 29.6 % yield). LC/MS [M+H]+ = 416, retention time = 1.89 minutes.

The synthetic route of 39226-96-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXO GROUP LIMITED; WO2008/119825; (2008); A2;,
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. 60811-18-9, name is 4-Bromo-1-chloro-2-fluorobenzene, This compound has unique chemical properties. The synthetic route is as follows., Formula: C6H3BrClF

EXAMPLE 219 (+)-(4aR)-(10bR)-4-methyl-8-(4-chloro-3-fluorophenyl)-10b-methyl-1,2,3,4,4a,5,6,10b-octahydrobenzo[f]quinolin-3-one STR237 A 15 mL round bottom flask was charged with (+)-(4aR)-(10bR)-4-methyl-10b-methyl-1,2,3,4,4a,5,6,10b-octahydrobenzo[f]quinolin-3-one-8-boronic acid (178 mg, 0.65 mmol), tetrakis(triphenylphosphine)palladium(0) (23 mg, 0.02 mmol), 1-bromo-4-chloro-3-fluorobenzene (136 mg, 0.65 mmol), 0.65 mL of 2M sodium carbonate and 2 mL of THF, fitted with a reflux condenser, and the stirred mixture was heated at 80, under nitrogen, for 24 h. The mixture was cooled, diluted with ethyl acetate (75 mL) and washed with brine (2*25 mL). The combined organic extracts were dried over sodium sulfate, concentrated, and purified by silica gel chromatography (ethyl acetate eluent) to give 125 mg (56%) of the title compound as an amorphous foam. FDMS: m/e=357. alpha[D]589 =+74.28 (c=0.35, chloroform).

According to the analysis of related databases, 60811-18-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Eli Lilly and Company; US5578724; (1996); A;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Electric Literature of 59681-66-2,Some common heterocyclic compound, 59681-66-2, name is 4-Chloro-N1-methylbenzene-1,2-diamine, molecular formula is C7H9ClN2, 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.

[000316] To a solution of Compound 10B (2.5 g, 16 mmol) in methanol (50 mL) was added triethoxymethane (2.8 g, 19 mmol) and sulfamic acid (155 mg, 1.6 mmol). The mixture was stirred at rt for 5 h. After removal of solvents, the mixture was diluted with water (30 mL) and extracted with ethyl acetate (50 mL x 3). The organic layer was dried over Na2S04. Filtration and evaporation of solvents gave a crude product Compound IOC (2.3 g, crude) as a red solid, which was used to next step without purification. LC-MS (m/z): 167 [M+l]+; 1H-NMR (CDC13, 400 MHz) major characteristic peaks: delta (ppm) 3.84 (s, 3H), 7.30 (d, J= 8.4 Hz, 1H), 7.61 (d, J= 8.8 Hz, 1H), 7.70 (s, 1H), 8.25 (s, 1H).

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-N1-methylbenzene-1,2-diamine, its application will become more common.

Reference:
Patent; BIOMARIN PHARMACEUTICAL INC.; WANG, Bing; CHU, Daniel; BRIDGES, Alexander, James; WO2015/42397; (2015); A1;,
Chloride – Wikipedia,
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Application of 6940-78-9, 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. 6940-78-9, name is 1-Bromo-4-chlorobutane, This compound has unique chemical properties. The synthetic route is as follows.

Step 1: Synthesis of 1-(4-Chlorobutyl)-1,5,6,7-tetrahydroindol-4-one To a solution of 1,5,6,7-tetrahydroindol-4-one (10.0 g, 74.0 mmol) in acetone (300 mL) was added powdered sodium hydroxide (3.26 g, 81.4 mmol) and the mixture stirred at ambient temperature for 0.25 hours. 1-Bromo-4-chlorobutane (9.38 mL, 81.4 mmol) was then added and the resulting mixture stirred at ambient temperature for 7 hours after which time TLC (ethyl acetate:dichloromethane 1:1) showed complete reaction. The reaction was gravity filtered to remove salts, and the filtrate concentrated to dryness under vacuum. The resulting residue was dissolved in dichloromethane (200 mL) and gravity filtered again to remove more salts. The filtrate was then washed with water, dried with sodium sulfate, filtered and the solvent removed under vacuum to yield an oil. Flash chromatography using 6 in. of silica gel in a 5.5 cm column eluding with 1:1 followed by 2:1 ethyl acetate:hexane on half of the residue yielded 9.0 g of an oil which contained ~6.0 g of pure product (72%) and ~3.0 g of acetone aldol condensation product (4-hydroxy-4-methyl-2-pentanone). The oil was taken to the next step without further purification.

The chemical industry reduces the impact on the environment during synthesis 1-Bromo-4-chlorobutane. I believe this compound will play a more active role in future production and life.

Reference:
Patent; HELTON, David; FICK, David; US2009/264443; (2009); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Some common heterocyclic compound, 33863-76-2, name is 1-Bromo-3-chloro-5-fluorobenzene, molecular formula is C6H3BrClF, 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

(First step) Preparation of 2-(3-chloro-5-fluorophenyl)-5-pentylpyrimidine A solution of 3-chloro-5-fluorophenylmagnesium bromide [prepared from 22.7 g (108.3 mmol) of 3-chloro-5-fluoro-bromobenzene and 2.7 g (111.0 mmol) of magnesium, and 100 ml of diethyl ether] in diethyl ether was added by drops to a mixture of 10 g (54.1 mmol) of 2-chloro-5-pentylpyrimidine, 0.4 g (0.5 mmol) of dichloro[1,1′-bis(diphenylphosphino) ferrrocene]palladium, and 300 ml of diethyl ether while being maintained at a temperature lower than -60 C., stirred at the same temperature for 1 hour, and then stirred at 10 C. for 10 hours. A diluted hydrochloric acid in an amount of 300 ml was added to the reaction mixture and extracted with 250 ml of heptane. The organic layer thus obtained was washed with a diluted aqueous sodium bicarbonate solution thrice and water thrice, and then dried over anhydrous magnesium sulfate. The solvent was distilled off under a reduced pressure and the residue was subjected to silica gel column chromatography (eluent: heptane/toluene=1/1) to obtain 11.0 g of a crude 2-(3-chloro-5-fluorophenyl)-5-pentylpyrimidine. (Yield: 72.8%) This product was used for the subsequent reaction without further purification.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 33863-76-2, its application will become more common.

Reference:
Patent; Chisso Corporation; US6329027; (2001); B1;,
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. 38762-41-3, name is 4-Bromo-2-chloroaniline, This compound has unique chemical properties. The synthetic route is as follows., SDS of cas: 38762-41-3

General procedure: Method A: To a solution of 3a (150 mg, 0.47 mmol) in a mixture of dry DME (3 mL) and dry EtOH (3 mL), bis(triphenylphosphine)palladium(II) dichloride (17 mg, 0.02 mmol) was added. After 30 min, a solution of sodium carbonate (299 mg, 2.82 mmol) in H2O(2 mL) and a solution of 5-formyl-2-furanylboronic acid 4 (93 mg,0.66 mmol) in dry EtOH (1.5 mL) were added in this order. The reaction was heated under reflux for 12 h. After this time, H2O (4 mL)was added at 25 C and the organic phase was extracted with EtOAc(3 5 mL), dried over sodium sulfate, filtered and evaporated in vacuo. The crude product was purified by flash chromatography on silica gel (2% EtOAc in petroleum ether) to give 5a as orange solid(79 mg, 60%). Method B: To a suspension of 16a (1.0 g, 4.8 mmol) in H2O (20 mL), HCl (37%, 2 mL) was added. The resulting solution was cooled at 0 C and a solution of sodium nitrite (397 mg, 5.76 mmol) in H2O (2 mL) was added dropwise. After 1 h, a solution of 17(400 mL, 4.8 mmol) in acetone (2 mL) and solid copper(II) chloride(128 mg, 0.96 mmol) were added. The mixture kept at 25 C for 12 h. EtOAc was added (3 10 mL) and the organic phase was separated, dried over sodium sulfate, filtered and evaporated in vacuo. The crude product was purified by flash chromatography on silica gel (2% EtOAc in petroleum ether) to give 5a as orange solid (1.23 g, 90%).

According to the analysis of related databases, 38762-41-3, the application of this compound in the production field has become more and more popular.

Reference:
Article; Vallone, Alessandra; D’Alessandro, Sarah; Brogi, Simone; Brindisi, Margherita; Chemi, Giulia; Alfano, Gloria; Lamponi, Stefania; Lee, Soon Goo; Jez, Joseph M.; Koolen, Karin J.M.; Dechering, Koen J.; Saponara, Simona; Fusi, Fabio; Gorelli, Beatrice; Taramelli, Donatella; Parapini, Silvia; Caldelari, Reto; Campiani, Giuseppe; Gemma, Sandra; Butini, Stefania; European Journal of Medicinal Chemistry; vol. 150; (2018); p. 698 – 718;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 19752-55-7, name is 1-Bromo-3,5-dichlorobenzene, 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 19752-55-7, SDS of cas: 19752-55-7

EXAMPLE 2 27 Grams of powdery magnesium (purity 99.5percent) was dispersed in 200 ml of diethyl ether. A solution obtained by dissolving 226 g of 1-bromo-3,5-dichlorobenzene in 800 ml of diethyl ether was added dropwise to the dispersion heated at about 40° C., and after the addition, the mixture was stirred at the same temperature for 2 hours to react them whereby 3,5-dichlorophenylmagnesium bromide was produced.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1-Bromo-3,5-dichlorobenzene, and friends who are interested can also refer to it.

Reference:
Patent; Ishihara Sangyo Kaisha Limited; US4230642; (1980); A;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Electric Literature of 139512-70-2, The chemical industry reduces the impact on the environment during synthesis 139512-70-2, name is 4-Chloro-5-fluorobenzene-1,2-diamine, I believe this compound will play a more active role in future production and life.

General procedure: Intermediate compound 5 (0.2 g, 1.24 mmol) and benzil 6d (0.26 g, 1.24 mmol) were weighed and dissolved in 20 mL glacial acetic acid. This mixture was refluxed for 2.5hr. The completion of reaction was monitored by TLC. The reaction mixture was cooled and poured into crushed ice. The precipitated product was filtered off and washed with cold water. The product was then purified by column chromatography using hexane: ethyl acetate as mobile phase. The pure fractions obtained were dried and concentrated to obtain white solids of product 7d. (yield 82%, m.p. 110-112 C).

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, 4-Chloro-5-fluorobenzene-1,2-diamine, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Patel, Saloni B.; Patel, Bhumika D.; Pannecouque, Christophe; Bhatt, Hardik G.; European Journal of Medicinal Chemistry; vol. 117; (2016); p. 230 – 240;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Some common heterocyclic compound, 7006-52-2, name is N-Methyl-3-chloroaniline, molecular formula is C7H8ClN, 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 N-Methyl-3-chloroaniline

The suitable omega-bromoalkanoyl chloride (0.7 mmol) was added dropwise to a stirred ice-cooled solution of the suitable aniline (0.33 mmol) and NaHCO3 (0.10 g, 1.22 mmol) in EtOAc (0.4 mL) and water (0.4 mL), and the resulting mixture was stirred at room temperature for 20 min. Water was added and the aqueous phase was extracted three times with EtOAc. The combined organic phases were washed with brine, dried (Na2SO4) and concentrated under reduced pressure to afford a crude residue that was used for the next step, without further purification.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 7006-52-2, its application will become more common.

Reference:
Article; Spadoni, Gilberto; Bedini, Annalida; Bartolucci, Silvia; Pala, Daniele; Mor, Marco; Riccioni, Teresa; Borsini, Franco; Cabri, Walter; Celona, Diana; Marzi, Mauro; Tarzia, Giorgio; Rivara, Silvia; Minetti, Patrizia; European Journal of Medicinal Chemistry; vol. 80; (2014); p. 8 – 35;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Application of 13918-92-8, In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 13918-92-8 as follows.

General procedure: To a mixture of 3-amino-2-methyl-thieno[2,3-d]pyrimidin-4(6H)-one (1.0 mmol) (8 and 9) and benzenesulfonyl chloride (1.1 mmol) in DCM (10 mL) was added dropwise pyridine (1.2 mmol) in dichloromethane (2 mL). The resulting mixture was stirred at room temperature for 12 hrs. The mixture was concentrated under reduced pressure, and theresidue was treated with water (30 mL). The aqueous mixture was neutralized by the addition of aqueous 10% HCl solution and extracted with DCM (230 mL). The organicphase was washed with aqueous saturated NH4Cl solution and brine. The organic layer was separated and dried over anhydrous MgSO4, filtered, and concentrated under reducedpressure to give the crude product, which was purified by silica gel chromatography to produce the pure corresponding compounds.

According to the analysis of related databases, 13918-92-8, the application of this compound in the production field has become more and more popular.

Reference:
Article; Nie, Li Fei; Bozorov, Khurshed; Huang, Guozheng; Zhao, Jiangyu; Niu, Chao; Aisa, Haji Akber; Phosphorus, Sulfur and Silicon and the Related Elements; vol. 193; 10; (2018); p. 656 – 667;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics