Category: 21667-62-9

Yadav, Maruti B.; Jeong, Yeon Tae published the artcile< A one-pot ring-closure and ring-opening sequence for the cascade synthesis of dihydrofurofurans and functionalized furans>, Application of C9H6ClNO, the main research area is dihydrofurofuran furan preparation triethylamine catalyst; aromatic aliphatic glyoxal cyanoacetophenone three component ring closure opening.

Authors have developed a simple novel ring-closure and ring-opening pathway using an organo-base system for the synthesis of highly substituted dihydrofurofuran and furan frameworks via a triethylamine-catalyzed one-pot three-component reaction. The protocol involved a Knoevenagel and Michael adduct via Paal-Knorr cyclization with aromatic/aliphatic glyoxal and 2-cyanoacetophenone under mild and heating conditions with excellent yields through a simple filtration method. The merits of this methodol., including the use of easily available feedstocks and an inexpensive catalyst, Gram-scale synthesis, wide functional group tolerance, an open-air reaction setup, and no need for workup and column-chromatog. procedures, make the developed methodol. a practical way to access dihydrofurofurans and functionalized furans.

Organic & Biomolecular Chemistry published new progress about Acetophenones Role: RCT (Reactant), RACT (Reactant or Reagent) (cyano). 21667-62-9 belongs to class nitriles-buliding-blocks, and the molecular formula is C9H6ClNO, Application of C9H6ClNO.

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Jia, Qianfa; Yin, Guoliang; Lan, Yunfei; Lin, Yinhe; Ren, Qiao published the artcile< Base-mediated Benzannulation Reactions for the Synthesis of Densely Functionalized Aryl α-Keto Esters>, Computed Properties of 21667-62-9 , the main research area is phenyl keto ester preparation; cyano phenyl methanone ynedione regioselective cycloaddition.

A novel and straightforward strategy for the construction of versatile densely functionalized aryl α-keto esters were disclosed through a one-pot and efficient [4+2] benzannulation reaction of α-cyano-β-methylenones and ynediones, which were synthesized easily from the corresponding starting materials. This protocol featured high yield, mild metal-free reaction condition, high atom economy, high functional-group tolerance, easy handing and gram-scale synthesis.

Asian Journal of Organic Chemistry published new progress about [4+2] Cycloaddition reaction (regioselective). 21667-62-9 belongs to class nitriles-buliding-blocks, and the molecular formula is C9H6ClNO, Computed Properties of 21667-62-9 .

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Some common heterocyclic compound, 21667-62-9, name is 3-(3-Chlorophenyl)-3-oxopropanenitrile, molecular formula is C9H6ClNO, 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. Computed Properties of C9H6ClNO

EXAMPLE 41 Preparation OF 3- [5-AMINO-4- (3-CHLOROBENZOYL)-PYRAZOL-1-YL]-N-CYCLOPROPYL-4- methyl-benzamide A. 2- (3-Chlorobenzoyl)-3-phenylaminoacrylonitrile A solution of 3-chlorobenzoylacetonitrile (476 mg, 2.66 mmol, 1.0 eq) and diphenylformamidine (522 mg, 2.66 mmol, 1.0 eq) in 25 mL of toluene was stirred at room temperature for 2h then heated to 100 C overnight. The solution was cooled and diluted with hexanes. The resulting solid was filtered and dried to provide the desired product (566 mg, 75%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 21667-62-9, its application will become more common.

Reference:
Patent; TRIAD THERAPEUCTICS, INC.; WO2005/9973; (2005); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Related Products of 21667-62-9, 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. 21667-62-9 name is 3-(3-Chlorophenyl)-3-oxopropanenitrile, 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.

Step A; 3-Amino-l-(3-chloro-phenyl)-propan-l-ol; To a stirred suspension of LAH (16 g, 90 mmol) in dry THF (200 mL) was added a solution of 3-(3-chlorophenyl)-3-oxopropanenitrile (10.4 g, 270 mmol) in dry THF (200 mL) dropwise at 0 C under nitrogen atmosphere. The mixture was warmed to 25 C and then heated at 60 C for 3 hours. After cooling to 0 C, a saturated solution of sodium hydroxide was added dropwise and extracted with ethyl acetate (200 mL). The solution was dried over anhydrous sodium sulfate and concentrated to dryness. The crude 3-amino-l-(3-chloro-phenyl)-propan-l-ol obtained was used in the next step without further purification. (Yield 14.5 g, crude).LC-MS: [M+H]+ 186.

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

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; LIU, Wenjian; LUK, Kin-Chun Thomas; ZHANG, Xiaohu; WO2012/98068; (2012); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

These common heterocyclic compound, 21667-62-9, name is 3-(3-Chlorophenyl)-3-oxopropanenitrile, 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. name: 3-(3-Chlorophenyl)-3-oxopropanenitrile

To 3-chlorobenzoylacetonitrile (24,360 mg, 2 mmol) and sulfur (76 mg) in DMF (4 [N-IL),] triethylamine (0.25mL) is added under stirring. To this solution tetrahydro-4H-pyran-4-one (1,200 mg, 2 mmol) is added dropwise. The mixture is stirred for 16 hours and it is poured into water (30 [ML),] which is extracted with diethyl ether (30 [ML).] The ethereal solution is dried with sodium sulfate and concentrated to give the desired compound as an orange solid (253 mg, 43%). Physical characteristics: MS [(ES+)] for [M/Z] 294,296 (M+H).

The synthetic route of 3-(3-Chlorophenyl)-3-oxopropanenitrile has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PHARMACIA & UPJOHN COMPANY; WO2004/35591; (2004); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Some common heterocyclic compound, 21667-62-9, name is 3-(3-Chlorophenyl)-3-oxopropanenitrile, molecular formula is C9H6ClNO, 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. name: 3-(3-Chlorophenyl)-3-oxopropanenitrile

EXAMPLE 41 Preparation OF 3- [5-AMINO-4- (3-CHLOROBENZOYL)-PYRAZOL-1-YL]-N-CYCLOPROPYL-4- methyl-benzamide A. 2- (3-Chlorobenzoyl)-3-phenylaminoacrylonitrile A solution of 3-chlorobenzoylacetonitrile (476 mg, 2.66 mmol, 1.0 eq) and diphenylformamidine (522 mg, 2.66 mmol, 1.0 eq) in 25 mL of toluene was stirred at room temperature for 2h then heated to 100 C overnight. The solution was cooled and diluted with hexanes. The resulting solid was filtered and dried to provide the desired product (566 mg, 75%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 21667-62-9, its application will become more common.

Reference:
Patent; TRIAD THERAPEUCTICS, INC.; WO2005/9973; (2005); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Application of 21667-62-9, 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. 21667-62-9 name is 3-(3-Chlorophenyl)-3-oxopropanenitrile, 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.

General procedure: A mixture of ethyl 3-oxo-3-phenylpropanoate (2a) (1.73 mL,10.00 mmol) and allylamine [(3.75 mL, 50.00 mmol) neutralized with acetic acid (2.86 mL, 50.00 mmol)] in ethanol (10 mL) was heated to reflux for 3 h. The resulting mixture was concentrated and the residue was taken up in CH2Cl2. The organic layer was washed with 5% HCl and water, dried over MgSO4 and concentrated. Purification of the crude product by flash column chromatography (silica gel; petroleum ether/ethyl acetate95:5) afforded 3a (2.08 g, 9.00 mmol) in 90% yield as a colourless liquid. When treated with 2c, it afforded 3c instead of 3-(allylamino)-3-(2-fluorophenyl) acrylonitrile.

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

Reference:
Article; Zhai, Sheng-Xian; Dong, Hong-Ru; Chen, Zi-Bao; Hu, Yi-Ming; Dong, Heng-Shan; Tetrahedron; vol. 70; 44; (2014); p. 8405 – 8412;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Synthetic Route of 21667-62-9,Some common heterocyclic compound, 21667-62-9, name is 3-(3-Chlorophenyl)-3-oxopropanenitrile, molecular formula is C9H6ClNO, 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 stirred suspension of LAH (16 g, 90 mmol) in dry THF (200 mL) was added a solution of 3-(3-chlorophenyl)-3-oxopropanenitrile (10.4 g, 270 mmol) in dry THF (200 mL) dropwise at 0 C. under nitrogen atmosphere. The mixture was warmed to 25 C. and then heated at 60 C. for 3 hours. After cooling to 0 C., a saturated solution of sodium hydroxide was added dropwise and extracted with ethyl acetate (200 mL). The solution was dried over anhydrous sodium sulfate and concentrated to dryness. The crude 3-amino-1-(3-chloro-phenyl)-propan-1-ol obtained was used in the next step without further purification. (Yield 14.5 g, crude). LC-MS: [M+H]+ 186.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3-(3-Chlorophenyl)-3-oxopropanenitrile, its application will become more common.

Reference:
Patent; Luk, Kin-Chun; US2012/184562; (2012); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Adding a certain compound to certain chemical reactions, such as: 21667-62-9, name is 3-(3-Chlorophenyl)-3-oxopropanenitrile, 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 21667-62-9, category: nitriles-buliding-blocks

To 3-chlorobenzoylacetonitrile (24,360 mg, 2 mmol) and sulfur (76 mg) in [DUT] [(4] mL), triethylamine (0. [25ML)] is added under stirring. To this solution [TETRAHYDROTHIOPYRAN-4-ONE] (11,232 mg, 2 mmol) is added dropwise. The mixture is stirred for 16 hours and it is poured into water (30 [ML),] which is extracted with diethyl ether (30 mL). The ethereal solution is dried with sodium sulfate and concentrated to give the desired compound as an orange solid (373 mg, [78%).] Physical characteristics: MS [(ES+)] for [M/Z] 294,296 (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; PHARMACIA & UPJOHN COMPANY; WO2004/35591; (2004); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

21667-62-9, 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. 21667-62-9 name is 3-(3-Chlorophenyl)-3-oxopropanenitrile, 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.

General procedure: To a stirred solution of carboxylic acid (1.0 eq.) in ethanol (2 M) was added thionyl chloride (2.0 eq.) dropwise at room temperature, and then refluxed for 2 hours. After it was cooled to room temperature, the reaction mixture was concentrated under reduced pressure to give crude product, which was chromatographed on silica gel column using 1:30 (v/v) EtOAc-petroleum ether solution as eluent to afford isolated product esters in 80% – 95% yields. Esters (1.0 eq.) were added dropwise to a stirred solution of acetonitrile (2.0 eq.) and NaH (3.0 eq.) in THF (2 M) at room temperature, and then refluxed for 1h . After it was cooled to room temperature, Water was added dropwise to the reaction mixture under ice bath until no gas bubbles generated, and employing dilute hydrochloric acid neutralization to neutral, extracted with ethyl acetate, dried over magnesium sulfate and concentrated in vacuo to give crude product which was chromatographed on silica gel column using 1:4 to 1:2 (v/v) EtOAc-petroleum ether solution as eluent to afford isolated product beta-ketonitriles, white or light yellow solid compounds in 50% – 85% yields. Finally, stirred in concentrated sulfuric acid (3 M) at room temperature for 5 to 10 hours. The reaction mixture was neutralized to neutral by ammonia water, extracted with ethyl acetate, dried over magnesium sulfate and concentrated in vacuo to give crude product which was chromatographed on silica gel column using 1:1 to 2:1 (v/v) EtOAc-petroleum ether solution as eluent to afford isolated product beta-ketoamides 1a-p, white solid compounds in 45% – 85% yields.

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

Reference:
Article; Zheng, Congke; Zhang, Xiaohui; Ijaz Hussain, Muhammad; Huang, Mingming; Liu, Qing; Xiong, Yan; Zhu, Xiangming; Tetrahedron Letters; vol. 58; 6; (2017); p. 574 – 577;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts