Month: July 2021

Synthetic Route of 16452-01-0, 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. 16452-01-0 name is 3-Methoxy-4-methylaniline, 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.

A mixture of 0.339 g (2 mmol) 2-Chlorobenzthiazole (commercially available) and 0.275 g (2 mmol) 3-methoxy-4-methylaniline (commercially available) in 4 ml acetic acid was heated to 115 C. for 4 h. After cooling to room temperature the mixture was subjected to preparative HPLC separation on reversed phase eluting with an acetonitrile/water gradient. The product fractions of Benzothiazol-2-yl-(3-methoxy-4-methyl-phenyl)-amine were evaporated to dryness and reacted according to the procedure described for Example 2 with 2-chlorobenzoyl chloride to yield the title compound. MS (m/e): 409.3 (MH+, 100%).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3-Methoxy-4-methylaniline, and friends who are interested can also refer to it.

Reference:
Patent; Nettekoven, Matthias Heinrich; Roever, Stephan; US2004/266845; (2004); A1;,
Ether – Wikipedia,
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Adding a certain compound to certain chemical reactions, such as: 60876-70-2, name is 1-Bromo-4-(tert-butoxy)benzene, belongs to ethers-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 60876-70-2, HPLC of Formula: C10H13BrO

[3-(4-Benzyloxy)phenoxy]benzo[b]thiophene-2-boronic acid was reacted with 4-(-tertbutoxy)bromobenzene according to the conditions described above for ?2-iodo-3-(4-benzyloxy)[phenoxy]-benzo[b]thiophene and 4-(tertbutoxy)phenyl boronic acid to give [2-(4-tertbutyloxyphenyl)-3-(4-benzyloxy)phenoxy]benzo[b] thiophene in 81% yield.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1-Bromo-4-(tert-butoxy)benzene, and friends who are interested can also refer to it.

Reference:
Patent; Eli Lilly and Company; US5856339; (1999); A;,
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Reference of 93919-56-3, 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. 93919-56-3 name is (4-(Trifluoromethoxy)phenyl)methanamine, 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.

(i) N-[4-(Trifluoromethoxy)benzyl]acetamide To a solution of 4-(trifluoromethoxy)benzylamine (3.46 g, 57.6 mmol) in DMF (75 mL) and acetic acid (10.0 g, 52.3 mmol) at -10 C. were added O-(benzotriazol-1-yl)-N,N,N’,N’-tetramethyluronium tetrafluoroborate (20.2 g, 62.8 mmol) and N,N-diisopropylethylamine (20.0 mL, 115 mmol) and the reaction mixture was stirred at room temperature overnight. Ethyl acetate (200 mL) was added and the organic phase was washed with water (100 mL), 0.25 M NaOH (100 mL), saturated aqueous NaHCO3 (100 mL), water (100 mL), 0.5 M HCl (100 mL), and water (100 mL), dried over MgSO4, and concentrated in vacuo to afford 11.2 g (92%) of a colourless oil. 1H NMR (600 MHz, CDCl3): delta 2.03 (s, 3H), 4.43 (d, 2H), 5.83 (bs, 1H), 7.17 (d, 2H), 7.31 (d, 2H). 13C NMR (125 MHz, CDCl3): delta 22.9, 42.8, 120.5 (q), 121.1, 129.0, 137.3, 148.4, 170.6.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, (4-(Trifluoromethoxy)phenyl)methanamine, and friends who are interested can also refer to it.

Reference:
Patent; Alstermark, Eva-Lotte Lindstedt; Olsson, Anna Christina; Li, Lanna; US2005/282822; (2005); A1;,
Ether – Wikipedia,
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Reference of 41789-95-1, These common heterocyclic compound, 41789-95-1, name is 1-(3-Methoxyphenyl)-N-methylmethanamine, 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: Catalytic acetic acid was added to a stirred solution of the appropriate formyl pyrimidine (1 eq) (ex: tert-butyl (tert-butoxycarbonyl)(4-((tert-butoxycarbonyl)(p- tolyl)amino)-6-formylpyrimidin-2-yl)carbamate) and the appropriate benzyl amine (1.5 eq) (ex: l-(3-methoxyphenyl)-N-methylmethanamine) in 1 ,2-dichloroethane at 0C then followed by sodium cyanoborohydride (2 eq) was added then the reaction mixture was stirred at room temperature for 16h. After completion of the reaction, the reaction mixture was quenched with minimum amount of saturated sodium bicarbonate solution, the organic product was extracted with dichloromethane (3x). The combined organic extracts were dried over anhydrous sodium sulfate. Solvent was distilled under reduced pressure to give the crude compound. The crude was purified by flash column chromatography (10-20% ethyl acetate/petroleum ether or 2-5% methanol/dichloromethane) to get the desired BOC protected product (ex: tert-butyl (tert-butoxycarbonyl)(4-((tert-butoxycarbonyl)(p- tolyl)amino)-6-(((3-methoxybenzyl)(methyl)amino)methyl)pyrimidin-2-yl)carbamate). (0942) In some examples, the reaction was carried out with trimethyl orthoformate (10 eq) and sodium triacetoxyborohydride (2.5 eq).

The synthetic route of 41789-95-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MINORYX THERAPEUTICS S.L.; GARCIA COLLAZO, Ana Maria; BARRIL ALONSO, Xavier; CUBERO JORDA, Elena; REVES VILAPLANA, Marc; ROBERTS, Richard Spurring; (213 pag.)WO2018/122775; (2018); A1;,
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Related Products of 14542-71-3, A common heterocyclic compound, 14542-71-3, name is 3,5-Dibromo-4-methylanisole, molecular formula is C8H8Br2O, 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.

Stage 2-9 – Intermediate A1 in Scheme 1 was synthesised in eight steps using processes described in patent WO 02/058695 ;

The synthetic route of 14542-71-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CHROMA THERAPEUTICS LTD.; WO2008/53158; (2008); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

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. 101-55-3, name is 1-Bromo-4-phenoxybenzene, This compound has unique chemical properties. The synthetic route is as follows., COA of Formula: C12H9BrO

A mixture of compound (III) (Pgi = Pg2 = Cbz) (973 mg, 2.00 mmol), Pd(OAc)2 (44 mg, 0.20 mmol), 1,10-phenanthroline (36 mg, 0.20 mmol), Cs2CO3 (716 mg, 2.20 mmol), 1-bromo-4- phenoxybenzene (548 mg, 2.20 mmol) and xylene (10 ml) was heated in a sealed tube under argon atmosphere at 140C for 16 h with intensive stirring. After completion of the reaction the tube was cooled to room temperature, carefully opened, and the reaction mass was poured into EtOAc (40 ml). After intensive stirring for 5 mm the obtained suspension was filtered through celite un evaporated in vacuum. The product was purified by column chromatography (eluent EtOAc-hexane 1:2, Rf 0.4). Yield 995 mg (76%), white amorphous powder.

According to the analysis of related databases, 101-55-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; LATVIAN INSTITUTE OF ORGANIC SYNTHESIS; LEBEDEVS, Antons; PONOMARJOVS, Jurijs; VARACEVA, Larisa; CERNAKS, Dmitrijs; CERNOBROVIJS, Aleksandrs; LAVRINOVICS, Edvards; (15 pag.)WO2017/39425; (2017); A1;,
Ether – Wikipedia,
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Reference of 2944-49-2,Some common heterocyclic compound, 2944-49-2, name is 1-Methoxy-2,3-dimethylbenzene, molecular formula is C9H12O, 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 2,3-dimethylanisole (10.00 g, 73.4 mmol) in acetonitrile (500 ml) was added to a mixture of copper(II) sulphate pentahydrate (18.14 g, 72.7 mmol) and potassium peroxodisulphate (59.81 g, 0.22 mol) in water (700 ml) and heated for 30 min at reflux. After cooling, water (100 ml) and dichloromethane (150 ml) were added and the phases were separated. The aqueous phase was extracted with dichloromethane (2×200 ml). The combined organic phases were dried over anhydrous sodium sulphate, filtered and concentrated on a rotary evaporator. 4:1 n-heptane/ ethyl acetate (200 ml) was added to the brown oil and this was filtered over silica gel. The filtrate was concentrated on a rotary evaporator. 4.63 g (30.8 mmol; 42%) of a gradually crystallizing yellowish oil was obtained.1H-NMR (CDCl3, 400 MHz): delta=10.63 (s, 1H; HC?O), 7.37 (t, 1H; J=8.0 Hz; Ar-H), 6.80 (m, 2H; Ar-H), 3.88 (s, 3H; O-CH3), 2.56 (s, 3H; Ar-CH3).13C-NMR (CDCl3, 100.6 MHz): delta=192.2 (C?O), 163.0 (Ar-C), 141.9 (Ar-C), 134.4 (Ar-CH), 123.9 (Ar-CH), 123.1 (Ar-C), 108.9 (Ar-CH), 55.6 (O-CH3), 21.4 (CH3).

The synthetic route of 2944-49-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Ivoclar Vivadent AG; Moszner, Norbert; Hendrik, John; Lamparth, Iris; Barner-Kowollik, Christopher; Krappitz, Tim; Feist, Fiorian; (14 pag.)US2020/79888; (2020); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Related Products of 93-04-9, 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. 93-04-9, name is 2-Methoxynaphthalene belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

A solution of bromine (first raw material storage tank 1) and 2-methoxynaphthalene in acetic acid (2-methoxynaphthalene in acetic acid solution(Second raw material storage tank 2) was successively passed through a microstructured mixer according to a molar ratio of 2-methoxynaphthalene and bromine of 1: 33,A heat exchanger 4,A tubular temperature control module 5 and a first microstructure reactor 6,In the first microstructure reactor 6Pressure and 55 C to stay 8. 5min reaction.at the same time,The first microstructure reactor 6 discharges the second microstructure reactor 7,In a second microstructure reactor 7 at atmospheric pressure and 85 C for 8 min,The second microstructure reactor 7 is discharged through a length of polytetrafluoroethylene capillary into the product collecting bottle 8,The polytetrafluoroethylene capillary was immersed in an ice-water bath to terminate the reaction.The second microstructure reactor is introduced into the ice water,A large number of solid precipitation,Filtration,Washed,The filter cake was dissolved in chloroform, washed with 10wt% Na0H aqueous solution, washed with water, dried over anhydrous sodium sulfate and evaporated to chloroform. The residue was recrystallized from anhydrous ethanol to give white needle crystals in a yield of 90.2% .

The synthetic route of 2-Methoxynaphthalene has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Nanjing University of Technology; GUO, KAI; FANG, ZHENG; HE, WEI; OUYANG, PINGKAI; (7 pag.)CN103664542; (2016); B;,
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35822-58-3, name is 2-Bromobenzaldehyde diethyl acetal, belongs to ethers-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. Computed Properties of C11H15BrO2

General procedure: In a 200 mL three necked flask equipped with a dropping funnel, a THF solution of S2 (1.0 equiv.)was slowly added to a mixture of Mg (1.1 equiv., pre-activated by stirring for several hours in vacuo)and THF. A THF solution of alkyne (1.1 equiv.) was subsequently added, and the reaction mixturewas stirred at room temperature. Then, HCl aq. (1M) was added, and the resultant solution wasextracted with Et2O. The organic layer was washed with Brine, dried over anhydrous Na2SO4,filtered, and concentrated in vacuo to yield a crude product including S3. If needed, the purificationwas performed by a column chromatography on a silica gel (eluted with 510% EtOAc/hexane).

The synthetic route of 35822-58-3 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Hoshimoto, Yoichi; Kumar, Ravindra; Nishimura, Chika; Ogoshi, Sensuke; Sasaoka, Yukari; Bulletin of the Chemical Society of Japan; vol. 93; 2; (2020); p. 182 – 186;,
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57478-19-0, name is 4-(4-(Trifluoromethyl)phenoxy)aniline, belongs to ethers-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. Computed Properties of C13H10F3NO

N-[4-(4-trifluoromethylphenoxy)phenyl]methanesulfonamide. (1b-1) To a solution of 4-(4-trifluoromethylphenoxy)aniline (15.18 g, 60 mmol) and pyridine (7.2 mL, 90 mmol) in dried CH2Cl2 (100 mL) under N2 at 0 C. was added methanesulfonyl chloride (5.22 mL, 66 mmol) dropwise. The mixture was stirred at 0 C. for 1 h and was then poured into CH2Cl2/H2O (100 mL/100 mL). 2N HCl(aq) (30 mL) was added into additional funnel. The organic layer was then washed with H2O (100 mL), brine (100 mL), dried (Na2SO4), and filtered. After removal of solvent, the crude product can be resolidified from Et2O/hexane to give 18.2 g of N-[4-(4-trifluoromethylphenoxy)phenyl]methanesulfonamide (92%) as a pale brown solid. 1H NMR (300 MHz, CDCl3) delta 7.58 (d, J=9.0 Hz, 2H), 7.30 (d, J=9.0 Hz, 2H), 7.04 (d, J=9.0 Hz, 4H), 6.93 (s, 1H, NH), 3.04 (s, 3H); MS (EI, m/z): 331 (M+), 330 (M+-1, 100).

The synthetic route of 57478-19-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; YANG, Shyh-Ming; Wang, Bingbing; Scannevin, Robert; Rhodes, Kenneth; Lagu, Bharat; Wilson, Lawrence J.; Karnachi, Prabha; Murray, William V.; US2008/85893; (2008); A1;,
Ether – Wikipedia,
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