Tag: M.W=100-200

Related Products of 39065-95-7,Some common heterocyclic compound, 39065-95-7, name is 4-(Chlorodifluoromethoxy)aniline, molecular formula is C7H6ClF2NO, 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 solution of 1-methyl-7-(pyrimidin-5-yl)-1H-benzo[d]imidazole-5-carboxylic acid (1g, 0.04 g, 0.157 mmol, 1 eq) and 4-(chlorodifluoromethoxy)aniline (33.50 mg, 0.173 mmol, 1.1 eq), HATU (71.79 mg, 0.189 mmol, 1.2 eq) in DMF (1 mL) at 15 C. was added DIEA (61.00 mg, 0.472 mmol, 82.21 uL, 3 eq). The mixture was stirred at 15 C. for 12 hours. LCMS showed ig was consumed completely and desired mass was detected. The mixture was concentrated, and the resulting residue was purified by prep-HPLC (FA condition, column: Luna C18 100*30 5u; mobile phase: [water (0.225% FA)-ACN]; B %: 35%-50%, 14 min) to afford the title compound 1 as a yellow solid. 1H NMR (400 MHz, MeOD-d4) delta 1N NMR (400 MHz, MeOD-d4) delta 9.31 (s, 1H), 9.06 (s, 2H), 8.45 (d, J=1.5 Hz, 1H), 8.39 (s, 1H), 7.91 (d, J=1.5 Hz, 1H), 7.84 (d, J=9.0 Hz, 2H), 7.31 (d, J=9.0 Hz, 2H), 3.60 (s, 3H).

The synthetic route of 39065-95-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Terns, Inc.; ROMERO, F. Anthony; KIRSCHBERG, Thorsten A.; HALCOMB, Randall; XU, Yingzi; (144 pag.)US2020/87283; (2020); A1;,
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,
Chlorides – an overview | ScienceDirect Topics

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

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 104-77-8,Some common heterocyclic compound, 104-77-8, name is 3-Chloro-N,N-diethylpropan-1-amine, molecular formula is C7H16ClN, 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 IV Bis[3-(diethylamino)propyl]6-oxo-6H-dibenzo[b,d] pyran-3,8-dicarboxylate dihydrochloride A mixture of 11.0 g (0.04 mole) of 6-oxo-6H-dibenzo [b,d]pyran-3,8-dicarboxylic acid, 18.0 g (0.12 mole) of gamma-diethylaminopropyl chloride and 400 ml of isopropyl alcohol are stirred and heated to its reflux temperature. A catalytic amount of benzyltrimethylammonium chloride. 0.3 ml of a 60% aqueous solution, is added and the reaction mixture heated to reflux for an additional 24 hours. On cooling, the reaction mixture is filtered, and the residue washed with isopropyl alcohol. This product is dissolved in boiling ethanol, treated with charcoal, filtered and cooled to room temperature. After standing for 1 hour, the gelatinous precipitate which appears is filtered and the filtrate cooled to -20C. The product which forms is filtered, washed with ethanol and again recrystallized from ethanol to yield the desired bis[3-(diethylamino)propyl] 6-oxo-6H-dibenzo[b,d]pyran-3,8-dicarboxylate dihydrochloride as a tan-colored solid, soluble in water and having a m.p. of 250-1C. (dec.) (placed in m.p. bath previously heated at 240 C.), lambdamax 294, and E1cm 1% 464.

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-N,N-diethylpropan-1-amine, its application will become more common.

Reference:
Patent; Richardson-Merrell Inc.; US3933893; (1976); A;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Electric Literature of 2687-12-9,Some common heterocyclic compound, 2687-12-9, name is Cinnamyl chloride, molecular formula is C9H9Cl, 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 mixture of cinnamyl chloride (905 ml, 6.5 mol), diisopropylamine (1.37 1, 9.75 mol), potassium carbonate (0.90 kg, 6.5 mol), potassium iodide (54 g, 0.325 mol), toluene (2.1 l) and methanol (0.50 1) is stirred at reflux temperature for 20 hours. The mixture is cooled to 25 C and water (5.2 1) is added. Phases are separated and the organic phase is extracted with brine. Organic phase is concentrated under reduced pressure (50 C) and then water (10.4 1) and toluene (2.6 l) are added and the pH is adjusted to 2 by addition of concentrated hydrochloric acid (-500 ml). The resulting mixture is stirred for 15 minutes and the phases are separated. The aqueous phase is re-extracted twice with toluene (2 x 2.6 l). Then the pH of the aqueous phase is adjusted to 12 by addition of 8 M aqueous sodium hydroxide solution (750 ml). To the resulting white suspension is added heptane (5.2 l) and the mixture is stirred for 15 minutes. Phases are separated and aqueous phase is re-extracted twice with heptane (2 x 2.6 l). Combined organic phases are dried over Na2SO4 and concentrated to give 1.32 kg (93 % yield) of DIPCA.

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

Reference:
Patent; LEK Pharmaceuticals d.d.; EP2364966; (2011); 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. 106131-61-7, name is 3,6-Dichloro-1,2,4,5-tetrazine, This compound has unique chemical properties. The synthetic route is as follows., Safety of 3,6-Dichloro-1,2,4,5-tetrazine

General procedure: In a 100 mL round bottom flask, was introduced the diol(0.66 mmol), s-collidine (0.79 mmol) and 20 mL of dry dichloromethane and the mixture was stirred at room temperature. 3,6-dichloro-s-tetrazine 1 (0.66 mmol) was dissolved in dry dichloromethane and added dropwise in the flask. After 2 h the reaction is complete (TLC) and the solvent was removed under reduced pressure. The crude residue was purified by column chromatography on silica gel (eluent from petroleum ether/ethyl acetate 7/3 to pure ethyl acetate). Compound 2a was isolated as pink solid in 58 % yield(0.22 g). M. p.: 131 C.1HNMR (400MHz, Acetone-d6): delta (ppm) 5.49 (t, 2H, 3JHF= 13.19Hz, (CF2)8CH2 – O); 4.18 (t, 2H, 3JH-F = 14.79 Hz,(CF2)8CH2 – OH). 13CNMR (100MHz, Acetone-d6): delta (ppm) 167.1 (CTz-O);166 (CTz-Cl); 100-120 ((CF2)8); 65.3 (t, 2JC-F = 26.83 Hz,(CF2)8CH2 – O); 60.4 (t, 2JC-F = 24.93Hz, (CF2)8CH2 – OH).19F NMR (376 MHz, Acetone-d6): delta (ppm) -119.93 (m,2F); -122.33 (m, 10F); -123.49 (m, 2F); -123.87 (m, 2F).

According to the analysis of related databases, 106131-61-7, the application of this compound in the production field has become more and more popular.

Reference:
Article; Guermazi, Refka; Royer, Lorna; Galmiche, Laurent; Clavier, Gilles; Audebert, Pierre; Hedhli, Ahmed; Journal of Fluorescence; vol. 26; 4; (2016); p. 1349 – 1356;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Related Products of 14752-66-0, A common heterocyclic compound, 14752-66-0, name is Sodium 4-chlorobenzenesulfinate, molecular formula is C6H4ClNaO2S, 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: In a typical experiment, 1,3-dicarbonyl compounds (1 mmol), sodium sulfinates (1.2 mmol), DMSO (8 mL) and NH4I (4 mmol) were added to the undivided cell. The electrosynthesis was carried out in the undivided cell fitted with a Ni sheet cathode (2 cmx2.5 cmx0.02 cm) and a graphite rod anode at a constantcurrent (50 mA) at room temperature under magnetic stirring for 2 h and then continuously stirring for 5 h. After the reaction was finished, the electrolyte solution was decolorized with Na2S2O3, and then washed with distilled water (50 mL) and extracted withethyl acetate (10 mLx3). The solvent was removed under reduced pressure, and the crude product was purified by column chromatography on silica gel using petroleum ether-ethyl acetate (5:1) as eluent.

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; Pan, Xiao-Jun; Gao, Jian; Yuan, Gao-Qing; Tetrahedron; vol. 71; 34; (2015); p. 5525 – 5530;,
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 39885-50-2 as follows. Quality Control of 2-Chloro-4-(trifluoromethyl)aniline

EXAMPLE 59 8-Chloro-N-((4-chlorophenyl)methyl)-4-hydroxy-5-trifluoromethyl-3-quinolinecarboxamide [] A mixture of 2-chloro-5-trifluoromethylaniline (3.91 g) and diethyl ethoxymethylenemalonate (4.0 mL) is heated at 190°C for 2 h and is then diluted with diphenyl ether (30 mL). The mixture is allowed to cool to rt, filtered, and the white solid is washed with hexane (2 x 10 mL) to afford 1.632 g of the diethyl aminomethylenemalonate. The resulting intermediate (2.63 g) is suspended in diphenyl ether (30 mL) and heated to reflux with a Dean-Stark trap for 3 h. The mixture is allowed to cool to rt and is then poured into hexane (50 mL). The solid is filtered and then washed with hexane (20 mL) and hexane/diethyl ether (1/1, 20 mL) to afford 1.273 g of the quinolinecarboxylate ethyl ester. The ester (400 mg) and 4-chlorobenzylamine (1.52 mL) are heated at 190 °C for 1 h. The resulting mixture is diluted with toluene (4 mL), allowed to cool to rt, and then poured into hexane (50 mL). The solvent is decanted and the remaining oil is crystallized (acetic acid, water) to afford 285 mg of the title compound as a brown solid. Physical characteristics are as follows: Mp 270-1 °C.1H NMR (300 MHz, DMSO) delta 12.33, 10.06, 8.68, 8.10, 7.86, 7.36, 4.52.13C NMR (100 MHz, DMSO) delta 175.05, 164.07, 144.36, 139.12, 138.20, 132.42, 131.85, 129.84, 128.77, 128.44, 126.70 (q), 125.84, 125.20, 122.22, 113.75, 42.00.IR (mull) 3187, 3091, 2925, 2855, 1657, 1604, 1567, 1531, 1462, 1417, 1377, 1366, 1348, 1307, 1272, 1210, 1158, 1139, 1128, 1106, 854, 841, 802, 726 cm-1.Anal. Found: C, 52.12; H, 2.78; N, 6.70; Cl, 16.85.MS (ESI-) for C18H11Cl2F3N2O2m/z 412 (M-H)-.

According to the analysis of related databases, 39885-50-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Pharmacia & Upjohn Company LLC; EP1042295; (2005); B1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics