Tag: M.W=100-200

Electric Literature of 93-50-5,Some common heterocyclic compound, 93-50-5, name is 4-Chloro-2-methoxyaniline, molecular formula is C7H8ClNO, 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.

A solution of 4-chloro-2-methoxyaniline (4.93 g, 31.3 mmol) in THF (70 ml) was treated with BOC-anhydride (11.00 ml, 47.4 mmol) and heated at 70 overnight. LCMS showed that most of starting materials were converted to product. The solution was treated with silica gel and evaporated under reduced pressure. The material was divided into two batches, each of which was chromatographed by Biotage MPLC (50 g silica gel column, 0 to 1% EtOAc in hexanes). Like fractions from the two columns were combined and evaporated under reduced pressure to provide a clear colorless liquid. Heptane (-80 mL) was added, then evaporated under reduced pressure to provide a clear, very viscous liquid. LCMS and NMR are consistent with tert-butyl 4-chloro-2-methoxyphenylcarbamate (7.66 g, 29.7 mmol, 95 % yield). 1H NMR (300 MHz, CHLOROFORM-d): delta ppm 8.08-7.96 (m, 1 H), 7.01 (br s, 1 H), 6.92 (dd, J=8.65, 2.20 Hz, 1 H), 6.83 (d, J=2.34 Hz, 1 H), 3.87 (s, 3 H), 1.53 (s, 9 H). LCMS: m/z 202 (loss of t-Bu).

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-2-methoxyaniline, its application will become more common.

Reference:
Patent; FORMA THERAPEUTICS, INC.; ASHWELL, Susan; CAMPBELL, Ann-Marie; CARAVELLA, Justin Andrew; DIEBOLD, R. Bruce; ERICSSON, Anna; GUSTAFSON, Gary; LANCIA, David R.; LIN, Jian; LU, Wei; WANG, Zhongguo; (141 pag.)WO2016/44782; (2016); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Related Products of 51114-68-2, 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 51114-68-2 as follows.

A solution of a (15 76 g, 100 mmol, 1.0 eq) in 3M HCI (100 mL) at 0 C was added dropwise a solution ofNaNC (7.59 g, 110 mmol, 1.1 eq) in water (20 mL). The mixture was stirred at 0 C for 30 min, then added to a solution of KI (49.8 g, 300 mmol, 3.0 eq) in water (40 mL). The resulting mixture was stirred at r.t. for 1 h, poured into water (100 mL), and extracted with EtOAc (150 mL x 2). The combined organic layers were washed with sat. NarSCb solution (50 mL x 2) and brine (50 ml, x 2) successively, and then dried with anhydrous NaiSOy filtered, and concentrated. The residue was purified by chromatography on silica gel (PE) to give b (26.0 g, 97%) as red liquid. LCMS: 2.68.9 i M · H | .

According to the analysis of related databases, 51114-68-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SILICON SWAT, INC.; CHAMBERLAIN, Brian T.; RICE, James M.; JERNIGAN, Finith E., III; SHERMAN, Woody; KULKARNI, Meghana M.; SHECHTER, Sharon; ALLEN, Bryce K.; TAN, Dazhi; MARINO, Kristen A.; LIN, Zhixiong; (292 pag.)WO2019/100061; (2019); 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. 2106-04-9, name is 3-Chloro-2-fluoroaniline, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 3-Chloro-2-fluoroaniline

4. 0M HCI in Dioxane (4.0 ml) was added to a stirred suspension of 7- (benzyloxy)-4- chloro-6-methoxyquinazoline (CAS Registry NOL62364-72-9, prepared as described in W098/13354, Example 1) (60 g, 0.2 mol) and 3-CHLORO-2-FLUOROANILINE (31.96 g, 0.22 mol) in acetonitrile (1200 ml). The reaction mixture was heated at 80C for 1 hour then left to stand overnight. Acetonitrile (500 ml) was added and the resulting precipitate filtered, washed with acetonitrile (3 x 500 ml) and dried under vacuum to give 7- (BENZYLOXY)-N- (3-CHLORO-2- fluorophenyl) -6-methoxyquinazolin-4-amine hydrochloride as a beige solid (85.45 g, 96%);

According to the analysis of related databases, 2106-04-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2005/26150; (2005); 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. 870-24-6, name is 2-Chloroethanamine hydrochloride, A new synthetic method of this compound is introduced below., Formula: C2H7Cl2N

Step-I: 2-(2-Methyl-1H-pyrrol-1-yl)ethanamineSodium hydroxide anhydrous (9.87 g, 0.246 mol, 4.0 eq.) and TBAHS (0.838 g, 0.002 mol, 0.04 eq.) were added to a solution of 2-methyl-1 H-pyrrole (5.0 g, 0.061 mol, 1.0 eq.) in acetonitrile (180 ml) at 0 C and the mixture was stirred at RT for 1 h. 2-Chloroethylamine hydrochloride (8.59 g, 0.074 mol, 1.2 eq.) was added to the reaction mixture and it was then heated at reflux for 16 h. The reaction mixture was cooled to RT, filtered through celite and washed with 10% MeOH/DCM (200 ml). The filtrate was concentrated under reduced pressure to give the crude product which was used in the next step without further purification.Yield: 100 %, crude (7.6 g, 0.061 mol)

The synthetic route of 870-24-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GRUeNENTHAL GMBH; REICH, Melanie; SCHUNK, Stefan; OBERBOeRSCH, Stefan; JOSTOCK, Ruth; GERMANN, Tieno; ENGELS, Michael; WO2012/28331; (2012); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

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 1939-99-7 as follows. HPLC of Formula: C7H7ClO2S

A stirred solution of ethyl(3-amino-2-oxo-1,2-dihydropyridyl)acetate (40.0 g, 0.204 mole) and 2,4,6-collidine (54 ML, 0.408 mole) in tetrahydrofuran (200 ML) was cooled in an ice bath.. A solution of benzylsulfonyl chloride (38.9 g, 0.204 mmole) in tetrahydrofuran (200 ML) was added over a 50-minute period.. After addition was complete, the solution was stirred for 30 minutes at 0 C. The reaction mixture was diluted with ethyl acetate (1.2 L), washed with 1.0N HCl (until aqueous layer is PH 1), water (50 ML), saturated sodium bicarbonate (100 ML), and brine (2*50 ML).. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was removed.. The residue was recrystallized from chloroform. 39 g of the title compound was isolated.. To the mother liquor was added silica gel.. The solution was swirled, then filtered through a sintered glass funnel, washing with 50% ethyl acetate in dichloromethane.. The solvent was removed from the filtrate, and the residue was recrystallized from chloroform.. An additional 13 g of the title compound was isolated to afford a total of 52.00 g (75% yield) of the title compound as a tan solid. Rf=0.32 (silica gel, 20% ethyl acetate in dichloromethane); m.p. 48-49 C.

According to the analysis of related databases, 1939-99-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Corvas International, Inc.; US6342504; (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. 106-39-8, name is 1-Bromo-4-chlorobenzene, A new synthetic method of this compound is introduced below., COA of Formula: C6H4BrCl

General procedure: To a mixture of aryl halide (0.3 mmol), NiCl2(H2O)1.5 [1] (0.0075 mmol, 2.5 mol percent), was charged dry THF (1 mL). The mixture was pumped and refilled with nitrogen for three times. The resulting mixture was stirred at -10 under nitrogen for 30 min. The reaction mixture was quenched through the addition of ice MeOH, then poured into a separatory funnel containing saturated aqueous NH4Cl (ca. 5 mL) and extracted with EtOAc (3 x 5 mL). The combined organic layers were washed with brine and dried over Na2SO4. The crude product was purified by column chromatography. Extent of isomerization can be easily determined via 1H NMR spectroscopy by comparison of the intergral of the singlet from the t-butyl group (1.3-1.4 ppm, 9H) to the integral of the doublet from the benzylic S3 protons of the i-butyl group (2.4-2.5 ppm, 2H). The doublet from the methyls of the i-butyl group could additionally be used (ca. 0.8 ppm, 6H).

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; Wu, Zhenghan; Si, Tengda; Xu, Guangqing; Xu, Bin; Tang, Wenjun; Chinese Chemical Letters; vol. 30; 3; (2019); p. 597 – 600;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 29671-92-9, name is Carbamimidic chloride 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 29671-92-9, COA of Formula: CH4Cl2N2

(1) Add methyl 3-amino-5-bromopyrimidinecarboxylate (6.2 g, 27 mmol) to a 250 mL sealed tube.Chloroformamidine hydrochloride (3.4 g, 30 mmol) and dimethyl sulfone (50.8 g, 20 mmol) were heated to 140oC and stirred for 6 hours. After cooling to room temperature, 50 mL of water was added to the reaction solution, followed by ultrasonication for 30 minutes. The residue was filtered. Water, acetone washing, vacuum drying to obtain a tan solid 1 (yield = 65%),

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

Reference:
Patent; Tsinghua University; Liao Xuebin; He Lei; Wang Zhisong; Gao Yan; (59 pag.)CN108069963; (2018); A;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 94-97-3, name is 5-Chloro-1H-benzo[d][1,2,3]triazole, 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 94-97-3, SDS of cas: 94-97-3

General procedure: A mixture of azole (0.2 mmol), ketone (0.3 mmol, 1.5equiv.), NaHCO3 (33.6 mg, 2.0 equiv.), I2 (101.6 mg, 2.0 equiv.), and 1,2-dichloroethane (2 mL) was stirred at 80 C for 24 h. After cooling to room temperature, the reaction mixture was quenched with a saturated solution of Na2S2O3 (5 mL) and extracted with ethyl acetate (3×5 mL). The combined organic phases were washed with brine (10 mL), dried over anhydrous magnesium sulfate, filtered, and concentrated. The residue was purified by flash column chromatograph, using a mixture of petroleum ether and ethyl acetate (5:1-2:1) as eluent to afford the corresponding products. The identity and purity of the products was confirmed by 1H and 13C NMR spectroscopic analysis.

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:
Article; Chen, Wenlin; Yan, Rulong; Tang, Dong; Guo, Shuaibo; Meng, Xu; Chen, Baohua; Tetrahedron; vol. 68; 38; (2012); p. 7956 – 7959;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

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 1005-56-7 as follows. Recommanded Product: 1005-56-7

Methyl-5-Jf-acetamido-3 , 5-dideoxy-3- f luoro- 8 , 9- 0-isopropylidene-4- O- (phenoxy) thiocarbonyl-D- eryt+/-ro-/?- L-manno-2 -nonulopyranosonate 19 :19To a solution of 18 (1.949 g, 5.1 mmol) in 70 mL dry DCM and 35 mL pyridine, phenylchlorothionoformate (761 muL, 5.6 mmol) was added at -400C and stirred for 30 minutes at this temperature. The mixture was then brought to room temperature and stirred for further 4 hours. MeOH (5 mL) was then added and after 10 minutes the -crude mixture was concentrated in .vacuo. and purified by column chromatography (EtOAc/MeOH 100:1) to give 19. Colorless solid (2.065 g, 76%) . 1H-NMR (400 MHz, CDCl3) delta 1.35 (s, 3H, Me2C), 1.40 (s, 3H, Me2C), 2.35 (s, 3H, NHAc), 3.49 (m, IH, H-5), 3.86 (s, 3H, OMe), 4.07 (dd, J = 21.5, 10.5 Hz, IH, H-9) , 4.37 (m, IH, H-9′), 4.45 (d, J = 4.9 Hz, IH, H-8), 4.58 (q, J = 2.7 Hz, IH, H-6), 5.16 (dd, J = 25.4, 1.7 Hz, IH, H-3), 5.69 (d, J = 3.6 Hz, IH, H-7), 6.11 (ddd, J = 8.7, 23.1 Hz, IH, H-4) , 6.25 (d, J = 8.2 Hz, IH, NHAc), 7.06 – 7.45 (m, 5H, OPh)

According to the analysis of related databases, 1005-56-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; THE UNIVERSITY OF BATH; WATTS, Andrew, Graham; WO2010/29302; (2010); 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. 3972-56-3, name is 1-tert-Butyl-4-chlorobenzene, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 1-tert-Butyl-4-chlorobenzene

20 parts of water,40 parts of acetone,And 20 parts of potassium carbonate were mixed,Three parts of raw material A are added. After stirring for 1 hour,10 parts of raw material B was charged, the temperature was raised to 50 ° C. while stirring,Stir for an additional 1 hour. after that,Concentrate using a rotary evaporator,And dried to obtain a dispersant.N – (4 – aminophenyl) acetamide was used as the raw material A of the dispersant preparation example,Using 1-tert-butyl-4-chlorobenzene as the raw material B,Dispersant 1 was obtained.

According to the analysis of related databases, 3972-56-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Dispersed materials Institute; Umemura, Kazuyuki; Ito, Shiho; Suzuki, Junji; Nishida, Atsushi; (15 pag.)JP2016/108519; (2016); A;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics