Tag: M.W=100-200

53297-70-4, 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. 53297-70-4, name is 4-Amino-3-methylbenzenesulfonamide, A new synthetic method of this compound is introduced below.

A cooled (0 0C) solution of e-chloropyhmidine^-carbonyl chloride (4.56 g; 25.8 mmol) in DCM (80 ml) was treated dropwise over 30 minutes with a solution of 4-amino-3-methyl-benzenesulfonamide (4.00 g; 21.5 mmol) and DIEA (7.40 ml; 43.0 mmol) in anhydrous DMF (10 ml_). At the end of addition the reaction mixture was concentrated under vacuum and the residue was taken up in EtOAc (200 mL). The organic phase was washed with water/brine (80 mL). A precipitate was formed, which was filtered and dried under vacuum to afford the crude product which was recrystallized from EtOH. The title product was obtained as a white solid. 1H NMR (300MHz, DMSO-d6) delta 10.65 (1 H, br s), 9.31 (1 H, d, J= 1.1 Hz), 8.24 (1 H, d, J= 1.1 Hz), 7.85-7.68 (3H, m), 7.33 (2H, br s), 2.36 (3H, s). MS (ESI-): 325.1. HPLC (Condition A): Rt 2.73 min (HPLC purity 100.0%).

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; LABORATOIRES SERONO SA; WO2009/19167; (2009); A1;,
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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 107017-73-2 as follows. 107017-73-2

Step 1 To a solution of tert-butyl (1-(hydroxymethyl)cyclopropyl)carbamate (Bioorg. Med. Chem. Lett., 2008, 18(6), 2188) (135 mg, 0.72 mmoles) in DCM (8 mL) was added Dess-Martin periodinane (277 mg, 0.65 mmole). After stirring 1 hr, the reaction was filtered through celite and concentrated to a yellow oil which was further purified by Isolera (7%-70% ethyl acetate/hexanes) to provide 84 mg (87%) of tert-butyl (l-formylcyclopropyl)-carbamate as a white solid.

According to the analysis of related databases, 107017-73-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Principia Biopharma Inc.; Goldstein, David Michael; US8673925; (2014); B1;,
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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. 57561-39-4, name is tert-Butyl (2-hydroxyethyl)(methyl)carbamate, This compound has unique chemical properties. The synthetic route is as follows., 57561-39-4

A 100 mL round-bottomed flask (rbf) equipped with a magnetic stirbar was charged withTHF (15 mL), water (15 mL) and 2-(methylamino)ethanol (2.00 mL, 25.0 mmol). To thestirred solution exposed to air Boc2O (5.9 g, 27 mmol) was added in 4 portions within 10min resulting in gas evolution. Several drops of sat. aq. NaHCO3 were added 40 min laterto keep the pH around 8. Most of THF was removed on a rotary evaporator 4.5 h after theBoc2O addition. The residue was transferred into a separatory funnel using EtOAc,washed with aq. 2.5 M NH4Cl (20 mL) and brine. The organic phase was dried overMgSO4, filtered into a 500 mL rbf and stripped of volatiles on the rotary evaporator.Using hexane transferred the crude product into a pre-weighed 100 mL rbf, removedvolatiles on the rotary evaporator (20 mm Hg). N-Methyl-N-Boc-aminoethanol wasobtained as colorless oil: 4.26 g (97%). A 3-neck rbf equipped with a magnetic stirbar, arubber septum, a glass stopcock (Teflon tape, central neck) and connected to a vacuumline was charged with 4.26 g of the protected amine (24.3 mmol). After evacuation andrefill with nitrogen 90 mL of THF freshly distilled from sodium-benzophenone ketyl wasadded. The flask was placed in an ice-water bath. Approx. 25 min later quickly added1.09 g of 60% NaH (27.2 mmol) in paraffin via the central neck. Approx. 20 min lateradded allyl bromide (2.15 mL, 24.8 mmol) with a syringe via the rubber septum followedby 0.4487 g of tetrabutylammonium iodide (1.21 mmol, 5 mol%) via the central neck.Approx. 2.5 h later removed the cold bath and let the reaction mixture stirring for 16 hunder nitrogen. The flask was immersed in ice-water bath followed by careful addition ofwater (20 mL, audible sound). The mixture was transferred into a 250 mL separatoryfunnel followed by addition of EtOAc (50 mL) and extraction. The organic phase was setaside and the aqueous phase was extracted with fresh portion of EtOAc (40 mL). Theorganic phases were combined, washed with aq. 2.5 M NH4Cl (50 mL) and brine, driedover MgSO4, filtered into a 500 mL rbf and stripped of volatiles on the rotary evaporatorleaving behind yellow oil, which was chromatographed on silica (normal phase, EtOAchexane,1:3) furnishing 3.7916 g of N-Methyl-N-Boc-aminoethanol O-allyl ether ascolorless oil (72% yield). N-Boc deprotection was achieved according to the method ofStrazzolini et al.1 To a 200 mL rbf charged with a magnetic stirbar and CH2Cl2 (22 mL)and immersed in an ice-water bath added 1.48 mL of conc. H2SO4 (assumed to be 17.9 M,26.5 mmol) with stirring. The central neck was plugged with a glass stopcock while adropping funnel was attached to the side-neck. A solution of 3.79 g of N-Methyl-N-BocaminoethanolO-allyl ether (17.6 mmol) in 65 mL CH2Cl2 was added to the solution ofacid dropwise from the addition funnel within 45 min followed by removal of cold bathand stirring at rt for 6 h. The dark purple mixture was transferred into a separatory funneland extracted with water (40 mL). The organic phase was extracted with additional 40mL of water, after which the aqueous extracts were combined in a 200 mL Erlenmeyerflask and basified by addition of NaOH (3.245 g in 15 mL water) with stirring. Theresulting solution was saturated with NaCl and extracted with three 50 mL portions ofCH2Cl2. Combined extracts were dried over Na2SO4, filtered into a 500 mL rbf andstripped of the solvent on the rotary evaporator (200 mm Hg). The resulting yellowish oilwas fractionated in vacuo using a one-piece distillation head and a receiving flask held at-50 C. The title compound was obtained as colorless oil (1.2208 g, 60% yield).

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; Kultyshev, Roman G.; Miyazawa, Akira; Tetrahedron; vol. 67; 11; (2011); p. 2139 – 2148;,
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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. 121492-06-6, name is N-Boc-(2-Aminoethyl)-N-methylamine belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. 121492-06-6

To a solution of 3-[8-(2,6-difluorophenyl)-2-(methylsulfinyl)-7-oxo-5, 6,7,8- tetrahydropyrimido[4,5-Patent; GLAXO GROUP LIMITED; WO2007/147109; (2007); A2;,
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A common heterocyclic compound, 57561-39-4, name is tert-Butyl (2-hydroxyethyl)(methyl)carbamate, molecular formula is C8H17NO3, 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. 57561-39-4.

A solution of tert-butyl (2-hydroxyethyl)(methyl)carbamate (6.0 g, 34.24 mmol) and triethylamine (6.92 g, 68.48 mmol) in dichloromethane (100 mL) was added dropwise methanesulfonyl chloride (4.68 g, 41.09 mmol) at 0 oC under nitrogen. The reaction was stirred for 1 h at 0 oC. The resulting solution was washed with water (3×20 mL). The organic phase was dried with anhydrous sodium sulfate. After filtration, the filtrate was concentrated under vacuum to afford 2-[tert-butoxycarbonyl(methyl)amino]ethyl methanesulfonate (8 g, 31.58 mmol, 92.2% yield) as a colorless oil. LCMS (ESI) [M+H]+ =254.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route tert-Butyl (2-hydroxyethyl)(methyl)carbamate, its application will become more common.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; GENENTECH, INC.; LIANG, Jun; MALHOTRA, Sushant; MENDONCA, Rohan V.; RAJAPAKSA, Naomi; SIU, Michael; STIVALA, Craig; TELLIS, John C.; WEI, BinQing; CHAN, Bryan K.; DROBNICK, Joy Alison; GAZZARD, Lewis J.; HEFFRON, Timothy; JONES, Graham; LAINCHBURY, Michael; MADIN, Andrew; SEWARD, Eileen; CARTWRIGHT, Matthew W.; GANCIA, Emanuela; FAVOR, David; FONG, Kin-Chiu; GOOD, Andrew; HU, Yonghan; (298 pag.)WO2020/23560; (2020); A1;,
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The chemical industry reduces the impact on the environment during synthesis 67442-07-3, name is 2-Chloro-N-methoxy-N-methylacetamide, I believe this compound will play a more active role in future production and life. 67442-07-3

C. Synthesis of Intermediate 22 [0210] A 3-neck flask was charged with 21 (100 g) and THF (800 mL). The solution was degassed three times by slowly applying vacuum, followed by breaking vacuum with nitrogen. The solution was cooled to -10 C. internal temperature. A solution of 2N i-PrMgCl solution in THF (125 g, 1.04 mole equiv) was added slowly while maintaining internal temperature at -10 C. to 0 C. The resulting mixture was then stirred for 30 minutes at -10 C. until reaction was complete. 2-Chloro-N-methoxy-N-methylacetamide (40.6 g, 1.20 mole equiv) was dissolved in MTBE (122 g, 1.22 wt equiv) and filtered through a 1 mum filter. The MTBE solution of the acetamide was then added slowly to the flask maintaining internal temperature at -10 C. to 0 C. Upon completion of the addition, the internal temperature was adjusted to 0 C. and agitated for 2 hours. After the reaction is complete, 1N HCl (750 g) was added slowly so that the internal temperature did not exceed 20 C. If necessary, the internal temperature was adjusted to 20 C. The layers were separated and the aqueous layer was extracted with MTBE (410 g). The organic layers were combined and dried over MgSO4. The MgSO4 was filtered off and rinsed with THF (200 g). The filtrate and rinse were concentrated under vacuum 10 volumes (1000 mL). Isopropanol (785 g) was added and small amounts of crystals began to form. This slurry was again concentrated under vacuum to 10 volumes (1000 mL). Isopropanol (785 g) was once again added and the slurry was concentrated under vacuum to 10 volumes (1000 mL). The internal temperature was adjusted to 20-25 C. and agitated for ca. 30 minutes. The slurry was filtered and rinsed with isopropanol (100 g) then dried under vacuum to provide 62.28 g (70.8%, 98% purity by HPLC) of the product 22 as an off-white to pale yellow solid. 1H NMR (400 MHz, CDCl3, delta): 8.19 (s, 1H), 8.12 (d, J=7.8 Hz, 1H), 7.82 (s, 1H), 7.67 (d, J=8.0 Hz, 2H), 7.52 (d, J=7.8 Hz, 1H), 4.71 (s, 2H). 19F NMR (376 MHz, CDCl3) delta -111.4 (s, 2F).

The chemical industry reduces the impact on the environment during synthesis 67442-07-3. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Gilead Sciences, Inc.; Scott, Robert William; Vitale, Justin Philip; Matthews, Kenneth Stanley; Teresk, Martin Gerald; Formella, Alexandra; Evans, Jared Wayne; US2013/324740; (2013); A1;,
Amide – Wikipedia,
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A common compound: 1943-79-9, name is Phenyl methylcarbamate, belongs to amides-buliding-blocks compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below. 1943-79-9

(2) A mixture of t-butyl 2-{[(3-fluoroalinino)carbothioyl]amino}ethylcarbamate (1.81g) prepared in above (1), alpha-bromo-4′-morpholinoacetophenone (1.56g) and ethanol (20ml) was stirred at 45C under nitrogen atmosphere. One hour later, resulted crystals were filtered to give tert-butyl {2-[2-[(3-fluorophenyl)imino]-4-(4-mnorpholinophenyl)thiazol-3(2H)-yl]ethyl}carbamate (1.76g). A mixture of thus obtained compound (1.76g), methanol (5ml) and 4N-HCl dioxane (50ml) was stirred at room temperature. Three hours later, the reaction mixture was concentrated in vacuo, and the insoluble materials were filtered off to give N-[3-(2-aminoethyl)-4-(4-morpholinophenyl)thiazol-2(3H)-idene]-3-fluoroaniline (1.57g). To a mixture of thus obtained compound (1.57g), aqueous 2N-sodium hydroxide solution (10ml) and tetrahydrofuran (20ml) was added phenyl N-methylcarbamate (907mg), and the mixture was stirred at 55C. Three hours later to the reaction mixture was added water, and the mixture was extracted with ethyl acetate. An organic layer was washed with brine and dried over sodium sulfate. After removal of the solvent in vacuo, the residue was crystallized from methanol to give the titled compound (810mg) as needles. mp:190-191C IR (KBr, cm-1): 3328, 2949, 2852, 1618, 1595, 1577. 1H-NMR (CDCl3): delta2.69 (3H, d, J=4.8), 3.26 (4H, t, J=4.8), 3.45 (2H, m), 3.89-3.93 (6H, m), 5.10-5.60(2H, m), 5.80 (1H, s), 6.80-6.93 (3H, m), 6.97 (2H, d, J=8.8), 7.28-54 (3H, m).

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, 1943-79-9, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Dainippon Sumitomo Pharma Co., Ltd.; EP2016945; (2009); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

34801-09-7, Name is N-(2-Aminophenyl)acetamide, 34801-09-7, belongs to amides-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.

General procedure (Method A): To a solution of aniline (32.25 mmol) in 30 ml of benzene was added p-TSA (12.25 g, 64.5 mmol), TEOF (4.7 g, 32.25 mmol), CuCl (10 mol %) at rt, mixture was heated to 50 C. Maintaining 50 C, powdered NaNO2 (2.09 g, 32.25 mmol) was added portion wise over 15 min, frothing was observed during the addition which subsided. The reaction mixture was maintained at the same temperature for 30 min to complete the reaction, monitored by TLC. The reaction mixture was cooled to rt, filtered to remove the solid precipitated, washed with EtOAc and organic layer was evaporated to dryness to get sticky residue, which was extracted with petroleum ether (60-80) followed by evaporation of solvent to yield the crude biaryl. It was purified by recrystallization from methanol/column chromatography ethyl acetate/petroleum ether (0.5:10) as eluent.

Statistics shows that N-(2-Aminophenyl)acetamide is playing an increasingly important role. we look forward to future research findings about 34801-09-7.

Reference:
Article; Chaturbhuj, Ganesh U.; Akamanchi, Krishnacharya G.; Tetrahedron Letters; vol. 52; 38; (2011); p. 4950 – 4953;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

53297-70-4, 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 53297-70-4 as follows.

General procedure: The chlorides 9a-j was dissolved in CH2Cl2 (20 mL) andadded dropwise to a stirred solution of 4-anilinesulfonamide(10.0 mmol) and NaHCO3 (1.26 g, 15.0 mmol) in CH3CN(80 mL). The mixture was heated at 70 C for 2h. The solution solutionwas evaporated, and poured to water, filtered to give asolid. This was purified by chromatography on silica gelusing CH2C12-MeOH (30: l) to give the title molecules 10a-t.The typical compound 10c was characterized with NMR andMS techniques. The detailed data is below.

According to the analysis of related databases, 4-Amino-3-methylbenzenesulfonamide, the application of this compound in the production field has become more and more popular.

Reference:
Article; Song, Zhendong; Wang, Ping; Huang, Shanshan; Wang, Changyuan; Wang, Rui-Rui; Yang, Liu-Meng; Zhen, Yuhong; Liu, Kexin; Zheng, Yong-Tang; Ma, Xiaodong; Medicinal Chemistry; vol. 13; 4; (2017); p. 398 – 405;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

1114-51-8, A common heterocyclic compound, 1114-51-8, name is N,N-Diethylpropionamide, molecular formula is C7H15NO, 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.

(1.43) from DAQ and N-diethylpropionamide the 2,6-bis-(diethylamino-1-propylene-imino)-anthraquinone having a melting point of 78 C.

The synthetic route of 1114-51-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Hoechst Aktiengesellschaft; US4078086; (1978); A;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics