Tag: M.W=200-300

Synthetic Route of 72505-21-6, A common heterocyclic compound, 72505-21-6, name is 4-(Trifluoromethyl)thiobenzamide, molecular formula is C8H6F3NS, 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.

To a solution of intermediate 15 (530.3 g, 2.59 mol) in EtOH (2.6 l) was added 2- chloro-3-oxo-butyric acid ethyl ester (465 ml, 1.3 eq) and the mixture was stirred at rt for 7 hours and at 70C for 14 hours. After cooling at 0C the precipitate was filtered and washed with cold EtOH (500 ml) to give the title compound (573.0 g, 1.89 mol) as a beige powder in a 73% yield; 1H NMR (CDCI3, 300 MHz) delta 7.9 (d, 2H), 7.6 (d, 2H), 4.3 (q, 2H), 2.65 (s, 3H), 1.25 (t, 3H).

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:
Patent; GLAXO GROUP LIMITED; WO2004/6924; (2004); A1;,
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Synthetic Route of 138-41-0,Some common heterocyclic compound, 138-41-0, name is Carzenide, molecular formula is C7H7NO4S, 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 4-(aminosulfonyl)benzoic acid (500 mg, 2.5 mmol) in MeOH (2 ml) at O0C is added thionylchloride (0.2 ml, 7.4 mmol). The reaction mixture is stirred at rt overnight. When TLC confirms the total consumption of the starting acid, the solvent and excess thionyl chloride are removed under reduced pressure to afford 400 mg (75 %) of the title compound, which was used in the next step without any further purification. LC/MS: (ES+):215.9, (ES-):214.1.

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

Reference:
Patent; APPLIED RESEARCH SYSTEMS ARS HOLDING N.V.; WO2007/23186; (2007); A1;,
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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. 144-80-9, name is N-((4-Aminophenyl)sulfonyl)acetamide belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Product Details of 144-80-9

2 mmol compound 1a or 1b and 0.194 g (2 mmol) potassiumthiocyanate in about 25 mL acetone were refluxed for 30 min. Theresulting solid (KCl) was removed by filtration. Then to this solutioncorresponding sulfonamides (2 mmol) in about 10 mL acetone wasadded dropwise, the mixture was stirred under reflux for 2 h. The resulting solution was evaporated under reduced pressure. Then,the residue was treated with the water to give crude product as awhite solid. The resulting crude product was stirred with diethyletherat room temperature for 1 h and then filtered. After theseexperimental procedures, the white colored substance was obtainedas pure.

The synthetic route of 144-80-9 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Koca, ?rfan; Yi?itcan, Serhat; Guemue?, Mehmet; Goekce, Halil; Sert, Yusuf; Journal of Molecular Structure; vol. 1204; (2020);,
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Related Products of 22117-85-7, 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 22117-85-7 as follows.

EXAMPLE 9 Preparation of the compound of formula STR15 Benzyl-piperazine, PCl3 and 2-methoxy-5-sulphamoyl-benzoic acid were reacted in a reactor in accordance with the method described in Example 1. The product of formula STR16 was separated, and debenzylated by catalytic reduction with 5% Pd on C in ethyl alcohol. The 2-methoxy-5-sulphamoyl-benzoylpiperazine obtained in this manner was reacted with acetyl chloride in a molar ratio of 1:1, in benzene in the presence of pyridine, was filtered off, washed and crystallized from a mixture of methanol and ethyl acetate.

According to the analysis of related databases, 22117-85-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Ravizza S.p.a.; US4940793; (1990); A;,
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Application of 621-38-5, A common heterocyclic compound, 621-38-5, name is 3-Bromoacetanilide, molecular formula is C8H8BrNO, 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: A dry argon-flushed Schlenk flask, equipped with a magnetic stirrer and a septum was charged with asolution of 1-iodo-1-(3′,4′,5′-trimethoxyphenyl)ethylene (48 mg, 0.15 mmol) in 1.5 mL of dry THF.The solution of i-PrMgCl¡¤LiCl (0.17 ml of 0.97 M solution in THF, 0.165 mmol) was added slowly at -20 C, and the reaction mixture was stirred at this temperature for 20 min to complete I/Mg exchange. 1 M solution of ZnCl2 (0.15 ml of 1 M solution in THF, 0.15 mmol) was added dropwise for 1 min at -20 C and the reaction mixture was warmed to room temperature. 3-(Methoxymethoxy)-4-methoxyphenyl iodide (44 mg, 0.15 mmol) was placed in a round bottom flask under argon. Solution of Pd(OAc)2 (1.35 mg, 0.006 mmol) and S-Phos (3.7 mg, 0.009 mmol) in 1 mlof THF was added, followed by dropwise addition of prepared solution of organo zinc reagent (0.15mmol) over a period of 1 min at room temperature. The reaction mixture was stirred at room temperature for 5 h, poured into saturated aq. NH4Cl solution and extracted with EtOAc. The organiclayer was washed with brine, dried over Na2SO4 and concentrated in vacuo and the residue was purified by flash chromatography on silica gel (petroleum ether/EtOAc, 5:1) to give 5a-OMOM (44mg, 0.122 mmol, 81%) as brown oil.

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; Malysheva, Yulia B.; Buchvalova, Svetlana Y.; Svirshchevskaya, Elena V.; Fokin, Valery V.; Fedorov, Alexey Y.; Synlett; vol. 24; 14; (2013); p. 1772 – 1776;,
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Related Products of 885-70-1, 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. 885-70-1, name is 5,11-Dihydropyrido[2,3-b][1,4]benzodiazepin-6-one, This compound has unique chemical properties. The synthetic route is as follows.

EXAMPLE 20 L-5,11-Dihydro-11-[[6-methyl-2,6-diazabicyclo[3.3.0]oct-2-yl]carbonyl]-6H-pyrido[2,3-b][1,4]benzodiazepin-6-one 2.6 g (0.021 mole) of L-2-methyl-2,6-diazabicyclo [3.3.0]octane were added dropwise to a mixture consisting of 11.2 ml of a 20% strength solution of phosgene in toluene, 50 ml of acetonitrile and 2.4 g (0.023 mole) of anhydrous sodium carbonate while externally cooling with ice. After 60 minutes, 4.5 g (0.021 mole) of 5,11-dihydro-6H-pyrido[2,3-b][1,4]benzodiazepin-6-one were added and the mixture was heated under reflux for 4 hours. The hot mixture was filtered, the precipitate was washed three times using 10 ml of hot acetonitrile each time and the combined filtrates were concentrated in vacuo to a total volume of 15 ml. The solution was cooled in an ice bath and the resulting crystal paste was filtered under suction. Recrystallisation from acetonitrile produced 2.1 g (27% of theory) of colourless crystals of m.p. 220-222 C., identical to the preparation made as in Example 6c according to mixed melting point and spectroscopic data. 5,11-Dihydro-11-[[7-methyl-3,7-diazabicyclo[3.3.0]oct-3-yl]carbonyl]-6H-pyrido[2,3-b][1,4]benzodiazepin-6-one of m.p. 157-159 C. (acetonitrile) 5,11-dihydro-11-[[10-methyl-4,10-diazatricyclo[5.2.1.02,6 ]dec-4- yl]carbonyl]-6H-pyrido[2,3-b][1,4]benzodiazepin-6-one of m.p. 218-220 C. (ethyl acetate) were obtained in corresponding manner.

The chemical industry reduces the impact on the environment during synthesis 5,11-Dihydropyrido[2,3-b][1,4]benzodiazepin-6-one. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Rudolf; Klaus; Engel; Wolfhard; Eberlein; Wolfgang; Trummlitz; Gunter; Mihm; Gerhard; Doods; Henri; Mayer; Norbert; US5179090; (1993); A;,
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Application of 112101-81-2, A common heterocyclic compound, 112101-81-2, name is R-5-(2-Aminopropyl)-2-methoxybenzenesulfonamide, molecular formula is C10H16N2O3S, 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 4:Preparation of By-Product (5-((R)-2-{Bis-[2-(2-ethoxy phenoxy)ethyI]amino}-propyl)-2-methoxy benzene sulfonamide)This example demonstrates how by-product 5-((R)-2-{Bis-[2-(2-ethoxyphenoxy) ethyl]amino}-propyl)-2-methoxybenzenesulfonamide is prepared by reacting the (R)- enantiomer of reactant-V according to prior processes. A round-bottomed flask is charged with 4.0 g (16.37 mmol) of (R)-reactant-V, 3.47 g (32.74 mmol) OfNa2CO4, 8.01 g (32.65 mmol) of the bromide form of reactant-VI, and 24 mL of N,N-dimethylformamide. Notably, alkyl phosphite solvent was not used in this example. The mixture is heated up to 80 C, and is stirred overnight at 80 C, and then the mixture is cooled down to about 20-25 C. EPO At this point, 40 mL of water and 40 mL of AcOEt are charged into the flask and the resulting mixture is then stirred for 30 minutes and left to decant. The organic phase is separated and then charged again into the flask, is reintroduced in the flask and washed with slightly acidic water (pH 5). The mixture is let to decant and the organic phase is dried with Na2SO4 and the solvent evaporated to obtain 8.96 g of crude 5-((R)-2-{Bis-[2-(2- ethoxyphenoxy)ethyl]amino}-propyl)-2-methoxybenzene sulfonamide. The crude product was purified by silica gel column chromatography (AcOEt as eluent) to obtain 6.29 g of 5- ((R)-2- {Bis-2-(2-ethoxyphenoxy)ethyl]amino } -propyl)-2-methoxybenzenesulfonamide, which still was unpurified and contained unused reactant-VI. A second silica gel column chromatography (CHCI3 as eluent) was performed to obtain 6.00 g of purified 5-((R)-2-{Bis- [2-(2-ethoxyphenoxy)ethyl]amino}-propyl)-2-methoxybenzenesulfonamide (yield 64%).Prior to purification by gel column chromotography, the crude product has approximately 9% (area) tamsulosin free base and approximately 73.3% (area) of the byproduct. Following purification by gel column chromotography, tamsulosin free base is not detected according to HPLC method 1 analysis.The 1H-NMR pMSO-d6, 300 MHz), delta (ppm) of the byproduct is characterized as follows: 0.94 (d, 3H, NCHCH3); 1.24 (t, 6H, OCH2CH3); 2.49 (m (overlapped with DMSO-d5), IH, Ar- CHA); 2.84 (dd, IH, Ar-CHB); 2.89-3.05 (complex signal , 5H, N(CH2-)2 and NH-CHCH3); 3.83 (s, 3H, OCH3); 3.78-4.01 (complex signal, 8H52 OCH2CH3 and 2 NHCH2CH2O); 6.79-6.94 (complex signal, 8H, Ar-H of Ar-OEt); 6.97 (broad s, 2H SO2NH2); 7.00, (d, IH, 3-H (Ar- SO2NH2)); 7.41 (dd, IH, 4-H (Ar-SO2NH2); 7.57 (d, IH, 6-H (Ar-SO2NH2));The 13C NMR (DMSO-d6, 300 MHz), delta (ppm) of the byproduct is characterized as follows: 14.9 (2CH3, 2 OCH2CH3); 15.3 (CH3, CHCH3); 38.3 (CH2 , ArCH2); 50.1 (2 CH2, 2 OCH2CH2N); 56.1 (CH3, OCH3); 59.2 (CH, CHCH3); 63.9 (2 CH2, 2OCH2CH3); 68.6 (2 CH2, 2 OCH2CH2N); 112.4 (CH, C3 (Ar-SO2NH2)); 113.6 , 113.7 and 120.9 (2 x 4CH (Ar-OEt)); 128.1 (CH, C6 (Ar-SO2NH2); 130.9 and 132.3 (2 x C, Ci and C5 (Ar-SO2NH2)); 134.3 (CH, C4 (Ar-SO2NH2); 148.4 and 148.5 2 X 2C (Ar-OEt); 154.2 (C, C2 (Ar-SO2NH2).

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:
Patent; MEDICHEM, S.A.; WO2007/4077; (2007); A2;,
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Related Products of 14437-03-7, A common heterocyclic compound, 14437-03-7, name is Methyl tosylcarbamate, molecular formula is C9H11NO4S, 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: The 4-substituted methyl (phenylsulfonyl)carbamate was dissolved in the chosen alcohol (2 mL) in a microwave vial, which was closed using an aluminum open-top seal with PTFE-faced septum. The reaction mixture was heated under microwave irradiation at 100-120 oC for 20-60 min. The crude reaction mixture was concentrated under reduced pressure and the residue was purified using silica gel column chromatography to yield the desired (aryl)carbamate.

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; Isaksson, Rebecka; Kumpi?a, Ilze; Larhed, Mats; Wannberg, Johan; Tetrahedron Letters; vol. 57; 13; (2016); p. 1476 – 1478;,
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Application of 21440-97-1, The chemical industry reduces the impact on the environment during synthesis 21440-97-1, name is 6-Bromo-4,4-dimethyl-1,4-dihydrobenzo[d][1,3]oxazin-2-one, I believe this compound will play a more active role in future production and life.

With a thermometer,Add 40g compound 17, to the 1L three-neck bottle of the condenser28.7 g carbazole, 32.3 g K2CO3, 0.62 g 1,10-Phenanthroline,Then 450 ml of DMF was added.Replace the air in the reaction system with nitrogen,Add 0.45 g of CuBr under nitrogen protection.Heat to 120 C for 10 h,After the TLC was monitored, the starting material was completely reacted and the stirring was stopped and lowered to room temperature.The reaction system is added to 3 volumes of water,The product was precipitated by stirring and filtered.The filter cake was completely dissolved in 500 ml of dichloromethane (DCM) and washed 3 times with water.150ml each time. The organic phase is dried and concentrated.The crude product was passed through a silica gel column to give compound 18 as a white solid, 43.1 g, yield 80.6%.

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, 6-Bromo-4,4-dimethyl-1,4-dihydrobenzo[d][1,3]oxazin-2-one, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Xi’an Ruilian New Materials Co., Ltd.; Sun Jun; Zhang Hongke; Liu Kaipeng; Yang Yan; Yang Dandan; Gao Renxiao; (34 pag.)CN108912138; (2018); A;,
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Electric Literature of 85006-25-3, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 85006-25-3 name is tert-Butyl (tert-butoxycarbonyl)oxycarbamate, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

To an ice cooled (0 C) solution of tert-butyl N-(tert-butoxycarbonyloxy)carbamate (4.90 g, 21.01 mmol) in anhydrous DMF (30 mL) under nitrogen was added portion-wise 60% sodium hydride in mineral oil (540 mg, 22.5 mmol) and stirred for 30 min. The reaction mixture was treated with dropwise addition of a solution of [N-3-(3-fluoro -4-morpholinylphenyl)-2-oxo-5-oxazolidinyl] methyl methane sulfonate (5.90 g, 15.8 mmol) in DMF (70 mL). The reaction mixture was stirred to room temperature for 64 h. The reaction mixture was diluted with water (210 mL) and extracted with ethyl acetate (3 * 100 mL) and the EtOAc extract was diluted with hexane (60 mL) and washed with water, brine, dried (Na2SO4), filtered and concentrated to give the crude as a brown oil. Silica gel column chromatography eluted with EtOAc-Hexane 2:1 gave the titled compound 24 [17] as a pale yellow viscous oil (6.27 g, yield, 77.8%). 1H-NMR (DMSO-d6, 600 MHZ): delta 7.51 (dd, 1H, J = 15.0 Hz, 2.5 Hz, phenyl H), 7.19 (dd, 1H, J = 8.8 Hz, 2.5 Hz, phenyl H), 7.09 (t, 1H J = 9.6 Hz, phenyl H), 4.87 (m, 1H, oxazolidinone H), 4.15 (t, 1H, J = 4.6 Hz, oxazolidinone H), 3.97 (m, 1H, oxazolidinone H), 3.82 (m, 1H, methylene H), 3.72-3.76 (br t, 5H, morpholine H and methylene H), 2.97 (br t, 4H, morpholine H), 1.41-1.48 (br, 18H). MS 511.2 (M+).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, tert-Butyl (tert-butoxycarbonyl)oxycarbamate, and friends who are interested can also refer to it.

Reference:
Article; Phillips, Oludotun A.; D’Silva, Roselyn; Bahta, Teklu O.; Sharaf, Leyla H.; Udo, Edet E.; Benov, Ludmil; Eric Walters; European Journal of Medicinal Chemistry; vol. 106; (2015); p. 120 – 131;,
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