Tag: M.W=100-200

Some common heterocyclic compound, 6609-56-9, name is 2-Methoxybenzonitrile, molecular formula is C8H7NO, 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. SDS of cas: 6609-56-9

General procedure: To a reaction tube charged with NBS (1.5 equiv, 0.3 mmol), catalyst (10 mol%, 0.02 mmol) and CH3CN (1.0 mL),was added para-chloroanisole 1a (0.2 mmol). After being stirred at room temperature for 12 h in dark, the reaction was quenched by saturated aq. solution of Na2S2O3 (2 mL). The resulting mixture was extracted by ethyl acetate (3 5 mL). The combined organic extracts were washed by brine (10 mL), dried over Na2SO4 and filtered through a pad of Celite. The filtrate was concentrated under reduced pressure and the residuewas purified by flash chromatography on a silica gel column with petroleum ether/dichloromethane (5:1) as the eluent to give 4.3.1. 2-Bromo-4-chloroanisole (2a)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 6609-56-9, its application will become more common.

Reference:
Article; Pramanick, Pranab Kumar; Hou, Zhen-Lin; Yao, Bo; Tetrahedron; vol. 73; 50; (2017); p. 7105 – 7114;,
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Application of 6629-04-5, These common heterocyclic compound, 6629-04-5, name is N-Cyanoacetylurethane, 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.

A mixture of 6-(4-amino-2,6-dichloro-phenoxy)-4-isopropyl-2-methyl-2H-pyridazin-3-one (67) (1O g, 30.47 mmol) in glacial acetic acid (60 mL) and concentrated hydrochloric acid (9.06 mL) cooled to 5-100C was treated dropwise with a solution of sodium nitrite (2.3 g, 32.3 mmol) in water (6 mL). The reaction was stirred at 5-100C for 30 min. At this time, EPO the reaction was treated with N-cyanoacetylurethane (5.34 g, 33.52 mmol) followed by a solution of sodium acetate (7.5 g, 91.41 mmol) in water (22.5 mL). The reaction was stirred at 5-100C for 30 min and then was diluted with water (50 mL). The resulting solids were collected by filtration, washed with a 1:1 mixture of glacial acetic acid:water (40 mL) followed by water (2 x 60 mL), dried under house vacuum, and then dried under vacuum at 500C to afford (2-cyano-2-{ [3,5-dichloro-4-(5-isopropyl-l-methyl-6-oxo-l,6-dihydro- pyridazin-3-yloxy)-phenyl]-hydrazono}-acetyl)-carbamic acid ethyl ester (68) (15.04 g, 95%) as an orange solid; ES(+)-LRMS for C20H20Cl2N6O5 (M+H)+ at m/z = 495. Exact Mass = 494.0872; Molecular Weight = 495.33.

Statistics shows that N-Cyanoacetylurethane is playing an increasingly important role. we look forward to future research findings about 6629-04-5.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; WO2007/9913; (2007); A1;,
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Adding a certain compound to certain chemical reactions, such as: 555-21-5, name is 4-Nitrophenylacetonitrile, belongs to nitriles-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 555-21-5, HPLC of Formula: C8H6N2O2

Step 1: 2-Methyl-2-(4-nitrophenyl)propanenitrile 4-Nitrophenyl acetonitrile (20 g, 123.45 mmol), tetrabutylammonium bromide (2.15 g, 6.6 mmol) and methyl iodide (58 g, 475.41 mmol) in CH2Cl2 (150 mL) were added to NaOH (13.5 g, 337.5 mmol) in water (130 mL). The reaction mixture was stirred for 20 hours at RT. The organic layer was separated, was dried over Na2SO4, and was evaporated to dryness. The residue was dissolved in diethylether, was filtered over celite and solvent was evaporated to obtain the title compound. Yield: 18 g (76%); 1H NMR (CDCl3, 300 MHz): delta 8.220-8.250 (d, 2H, J=9 Hz), 7.627-7.657 (d, 2H, J=9 Hz), 1.750 (s, 6H).

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-Nitrophenylacetonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Kumar, Sanjay; Vishwakarma, Ram; Mundada, Ramswaroop; Deore, Vijaykumar; Kumar, Pramod; Sharma, Somesh; US2012/108627; (2012); A1;,
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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. 64248-64-2, name is 2,5-Difluorobenzonitrile, A new synthetic method of this compound is introduced below., name: 2,5-Difluorobenzonitrile

A suspension of 2,5-diflurobenzonitrile (4.5 g, 32.35 mmol) and 1,2,4-triazole sodium salt (3.6 g, 40 mmol) in dimethylformamide (40 mL) was heated at 80 C. for 15 h. The reaction mixture was then cooled, diluted with CH2Cl2 (200 mL), washed with water (3×30 mL) and brine (30 mL), then dried (Na2SO4), filtered and concentrated to give a white solid which was purified by flash column chromatography (SiO2) using 1:1 to 3:1 ethyl acetate/Hexanes to afford the title compound (2.98 g, 49% yield) as a white powder. 1H NMR (500 MHz, CDCl3) ?: 8.70 (1H, s), 8.18 (1H, s), 7.76 (1H, dd, J=9.0, 4.8 Hz), 7.55 (1H, dd, J=7.3, 2.8 Hz), 7.51-7.47 (1H, m). LCMS (M+H) calcd for C9H6FN4: 189.17; found: 189.10.

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; Naidu, B. Narasimhulu; Banville, Jacques; Beaulieu, Francis; Connolly, Timothy P.; Krystal, Mark R.; Matiskella, John D.; Ouellet, Carl; Plamondon, Serge; Remillard, Roger; Sorenson, Margaret E.; Ueda, Yasutsugu; Walker, Michael A.; US2005/267105; (2005); A1;,
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Electric Literature of 622-75-3, A common heterocyclic compound, 622-75-3, name is 2,2′-(1,4-Phenylene)diacetonitrile, molecular formula is C10H8N2, 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.

Ag(CF3SO3) (0.0231g, 0.090mmol) and p-phda (0.0281g, 0.180mmol) were dissolved in 10mL benzene. After stirring for 30min, the resultant solution were transformed to a Teflon-lined stainless steel vessel (25mL) and heated at 120C for 2h, and then cooled to room temperature naturally. The resulting colorless crystals of 2 were isolated by slow evaporation the solution in air. Yield: 69.80% (based on Ag). Anal. Calc. for C21H16AgF3N4O3S C, 44.30; N, 9.84; H, 2.83; Found: C, 44.03; N, 9.74; H, 2.70%. IR:(KBr, nu/cm-1): 2960(w), 2918(w), 2258(w), 1521(m), 1427(m), 1410(m), 1288(s), 1255(s), 1224(m), 1174(s), 1031(s), 933(m), 785(m), 761(m), 629(s), 519(m).

The synthetic route of 622-75-3 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Han, Jing; Yang, Jian; Yu, Zhong; Wang, Quan-jiu; Inorganica Chimica Acta; vol. 469; (2018); p. 318 – 324;,
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Electric Literature of 7251-09-4,Some common heterocyclic compound, 7251-09-4, name is 4-Amino-2-methoxybenzonitrile, molecular formula is C8H8N2O, 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: To an ice-cold suspension of nicotinoyl chloride hydrochloride(I) (1.78 g, 10 mmol) and appropriate 4-aminobenzonitrile (IIa-g) (10 mmol, 1.0 equiv) in acetonitrile(50 ml) under nitrogen was added triethylamine (8.1 g, 11.15 ml,40 mmol, 4.0 equiv) dropwise over 30 min. The resulting suspensionwas stirred at 0 C for 1 h then at room temperatureovernight. The reaction mixture was evaporated, diluted withEtOAc, washed with 10% HCl, brine, dried over anhydrousNa2SO4 and concentrated in vacuo. The resulting solid waswashed with diethyl ether and dried to yield the desired compounds(IIIa-g) in 50-90% yield.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4-Amino-2-methoxybenzonitrile, its application will become more common.

Reference:
Article; Dokla, Eman M.E.; Fang, Chun-Sheng; Abouzid, Khaled A.M.; Chen, Ching S.; European Journal of Medicinal Chemistry; vol. 182; (2019);,
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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. 7357-70-2, name is 2-Cyanothioacetamide, A new synthetic method of this compound is introduced below., Safety of 2-Cyanothioacetamide

To a solution of [CC-CYANOTHIOACETAMIDE] (0.5 g, 5 mmol) in DMF (3 mL) [A-BROMOACETOPHENONE] (1 g, [5] mmol, dissolved in 3 mL of DMF) was slowly added (dropping funnel). Approximately 30min after the addition the mixture was heated to [70C] for 30min, after which the reaction was complete as judged by TLC (SiO2; hexane/AcOEt 8: 2, [RF=0.] 3) The dark solution was poured onto water (50 mL) and extracted with AcOEt (3 x 30 mL). The combined organic phases were dried over [NA2SO4] and concentrated under vacuum. The resultant oily residue was dissolved in EtOH (2 mL) and poured in water (30 mL). After 1 hour stirring at room temperature the formed solid was filtered off, washed with [H20] and dried under vacuum (2 h, [50C] ; 48 h, [25C).] Pure [4-phenylthiazol-2-yl] acetonitrile (3,0. 87 g, 87%) was obtained. Analytical data [‘H-NMR] [(DMSO-D6,] [8)] : 7.9 (bd, 2H); 7.26-7. 5 [(M,] 4H); 4.2 (s, 2H) M. P. = [60C]

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; NOVUSPHARMA S.P.A.; WO2003/105842; (2003); A1;,
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Adding a certain compound to certain chemical reactions, such as: 2182-39-0, name is 2-(Phenylamino)propanenitrile, belongs to nitriles-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 2182-39-0, Application In Synthesis of 2-(Phenylamino)propanenitrile

d) 5-[1-Ethyl-4-(2-trimethylsilanyl-ethoxymethoxy)-1H-indol-6-ylmethyl]-pyrimidine-2,4-diamine. This compound was produced from 1-ethyl-4-(2-trimethylsilanyl-ethoxymethoxy)-1H-indole-6-carbaldehyde (630 mg, 1.97 mmol), 2-anilinopropionitrile (324 mg, 2.17 mmol), and guanidine hydrochloride (634 mg, 6.60 mmol), following the procedure detailed in Example 4, step f. Yield: 425 mg (53%). Yellow solid. MS (ISP): 414.4 ([M+H]+)

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:
Patent; Mattei, Patrizio; Pflieger, Philippe; US2003/119857; (2003); A1;,
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Related Products of 57381-51-8, 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. 57381-51-8, name is 4-Chloro-2-fluorobenzonitrile, This compound has unique chemical properties. The synthetic route is as follows.

EXAMPLE 14 2-(4-Chloro-2-ethoxy-phenyl)-4,5-bis-(4-chloro-phenyl)-4,5-dihydro-1H-imidazole To a solution of 4-chloro-2-fluoro-benzonitrile (1 g, 6.428 mmol) in ethanol (10 mL) were added sodium ethoxide solution (4.8 mL, 12.86 mmol, 21% wt in ethanol). The reaction mixture was heated at gently reflux for 12 h. The solvent was removed and the residue was partitioned between water (10 mL) and diethyl ether (20 mL). The layers were separated and the product was extracted with diethyl ether (20 mL). The organic layers were washed with brine (5 mL) and dried over anhydrous sodium sulfate. The solid was filtered off, and the filtrate was concentrated in vacuo. Purification of the residue by flash chromatography (Biotage system, KP-Sil 32-63 mum, 60 A silica gel) eluding with 5% ethyl acetate in hexanes yielded 4-chloro-2-ethoxy-benzonitrile (670 mg, 57%). Hydrogen chloride gas was passed through a solution of 4-chloro-2-ethoxy-benzonitrile (670 mg, 3.689 mmol) in anhydrous ethanol (25 mL) cooled to 0 C. After 45 min, the hydrogen chloride gas was stopped and the reaction vessel was sealed with a Teflon stopper. It was stirred at room temperature for 5 d. The reaction vessel was cooled to 0 C. and the stopper was removed. The solvent was removed and the residue was triturated in diethyl ether to afford ethyl 4-chloro-2-ethoxy-benzimidate hydrochloride (913 mg, 94%). It was used without further purification. To a solution of meso-1,2-bis-(4-chloro-phenyl)-ethane-1,2-diamine (810 mg, 2.879 mmol) and ethyl 4-chloro-2-ethoxy-benzimidate hydrochloride (913 mg, 3.455 mmol) in ethanol (10 mL) was added triethylamine (605 muL, 4.319 mmol). The reaction mixture was heated at gentle reflux for 4 h. The solvent was evaporated to dryness and the residue was purified by flash chromatography (Biotage system, KP-Sil 32-63 mum, 60 A silica gel) eluding with 70% ethyl acetate in hexanes to afford 2-(4-chloro-2-ethoxy-phenyl)-4,5-bis-(4-chloro-phenyl)-4,5-dihydro-1H-imidazole (1.045 g, 81%). HR-MS (ES, m/z) calculated for C23H20N2OCl3 [(M+H)+]445.0636, observed 445.0644.

The chemical industry reduces the impact on the environment during synthesis 4-Chloro-2-fluorobenzonitrile. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Hoffmann-La Roche Inc.; US6617346; (2003); B1;,
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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. 2338-75-2, name is 4-(Trifluoromethyl)phenylacetonitrile, A new synthetic method of this compound is introduced below., Quality Control of 4-(Trifluoromethyl)phenylacetonitrile

Step 1: Preparation of Intermediate 2-(4-Trifluoromethyl-phenyl)-ethylamine (I-16a) (4-Trifluoromethyl-phenyl)-acetonitrile (2 g, 10.81 mmol) in methanolic ammonia (50 mL) was added to Raney nickel (400 mg) in methanol taken in a parr hydrogenator. The flask was stirred at 50 PSI overnight. The reaction was monitored by TLC (10% methanol in CHCl3). The reaction mixture was filtered through celite bed and the filtrate was dried under reduced pressure to afford 2 g of the product (97.89% yield). LCMS purity: 98.73%, m/z=190.0 (M+1)

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; NOVARTIS AG; Bock, Mark Gary; Gaul, Christoph; Gummadi, Venkateshwar Rao; Moebitz, Henrik; Sengupta, Saumitra; US2014/45872; (2014); A1;,
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