Category: 15760-35-7

Application of 15760-35-7, A common heterocyclic compound, 15760-35-7, name is 3-Methylenecyclobutanecarbonitrile, molecular formula is C6H7N, 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.

Step 1 (0730) To a solution of compound 21-1 (5 g, 62 mmol) and RuCl3 (0.25 g, 1.4 mmol) in CH3CN/DCM/H2O (100 mL/100 mL/150 mL) at 0 C. was added NaIO4 (47.3 g, 250 mmol). The mixture was stirred at RT overnight, quenched with water, and extracted with DCM. The combined extracts were washed with brine, dried over Na2SO4, concentrated and purified by silica gel chromatography (PE: EA=5:1) to give 4.5 g of compound 21-2. 1H NMR (400 MHz, CDCl3): delta 3.53-3.55 (m, 4H), 3.23-3.29 (m, 1H).

The synthetic route of 15760-35-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Merck Sharp & Dohme Corp.; Wu, Wen-Lian; Burnett, Duane A.; Stamford, Andrew W.; Cumming, Jared N.; Asberom, Theodros; Bennett, Chad; Sasiskumar, Thavalakulamgara K.; Scott, Jack D.; US9181236; (2015); B2;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Synthetic Route of 15760-35-7,Some common heterocyclic compound, 15760-35-7, name is 3-Methylenecyclobutanecarbonitrile, molecular formula is C6H7N, 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.

into a 500-mL 3-necked round-bottomflask, was placed a solution of 3-methylidenecyclobutane-1-carbonitrile (1.5 g, 16.11 mmol,1.00 eq.) and RuC13.H20 (360 mg, 1.60 mmol, 0.10 eq.) in DCMIACN/H20 (60/60/90 mL). This was followed by the addition of sodium periodate (5.2 g, 24.31 mmol, 1.50 eq.), in portions at 10C in 15 mm. The resulting solution was stirred for 2 hours at 25 C. The solids were filtered out. The resulting solution was extracted with dichloromethane (3×100 mL) andthe organic layers combined. The resulting mixture was washed with brine (2×200 mL), dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (1:1). This resulted in 1.1 g (72%) of 3- oxocyclobutane-1-carbonitrile as a yellow solid.

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

Reference:
Patent; BASTOS Cecilia M.; MUNOZ Benito; TAIT Bradley; WO2015/196071; A1; (2015);,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Related Products of 15760-35-7, A common heterocyclic compound, 15760-35-7, name is 3-Methylenecyclobutanecarbonitrile, molecular formula is C6H7N, 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.

Step 1 (0730) To a solution of compound 21-1 (5 g, 62 mmol) and RuCl3 (0.25 g, 1.4 mmol) in CH3CN/DCM/H2O (100 mL/100 mL/150 mL) at 0 C. was added NaIO4 (47.3 g, 250 mmol). The mixture was stirred at RT overnight, quenched with water, and extracted with DCM. The combined extracts were washed with brine, dried over Na2SO4, concentrated and purified by silica gel chromatography (PE: EA=5:1) to give 4.5 g of compound 21-2. 1H NMR (400 MHz, CDCl3): delta 3.53-3.55 (m, 4H), 3.23-3.29 (m, 1H).

The synthetic route of 15760-35-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Merck Sharp & Dohme Corp.; Wu, Wen-Lian; Burnett, Duane A.; Stamford, Andrew W.; Cumming, Jared N.; Asberom, Theodros; Bennett, Chad; Sasiskumar, Thavalakulamgara K.; Scott, Jack D.; US9181236; (2015); B2;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Reference of 15760-35-7,Some common heterocyclic compound, 15760-35-7, name is 3-Methylenecyclobutanecarbonitrile, molecular formula is C6H7N, 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.

into a 500-mL 3-necked round-bottomflask, was placed a solution of 3-methylidenecyclobutane-1-carbonitrile (1.5 g, 16.11 mmol,1.00 eq.) and RuC13.H20 (360 mg, 1.60 mmol, 0.10 eq.) in DCMIACN/H20 (60/60/90 mL). This was followed by the addition of sodium periodate (5.2 g, 24.31 mmol, 1.50 eq.), in portions at 10C in 15 mm. The resulting solution was stirred for 2 hours at 25 C. The solids were filtered out. The resulting solution was extracted with dichloromethane (3×100 mL) andthe organic layers combined. The resulting mixture was washed with brine (2×200 mL), dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (1:1). This resulted in 1.1 g (72%) of 3- oxocyclobutane-1-carbonitrile as a yellow solid.

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

Reference:
Patent; BASTOS Cecilia M.; MUNOZ Benito; TAIT Bradley; WO2015/196071; A1; (2015);,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Application of 15760-35-7, A common heterocyclic compound, 15760-35-7, name is 3-Methylenecyclobutanecarbonitrile, molecular formula is C6H7N, 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) 50 g (0.54 mol) of 3-methylenecyclobutanecarbonitrile are dissolved in 600 ml of water and 50 ml of ether, cooled to 5 C., and 100 mg (0.4 mmol) of osmium(IV) oxide are added. 260 g (1.2 mol) of sodium periodate are then added in portions at the temperature indicated, and the mixture is allowed to warm to RT. The organic phase is extracted with dichloromethane and, after drying and evaporation, chromatographed over silica gel, giving 25 g (49%) of 3-oxocyclobutanecarbonitrile as colourless crystals (m.p. 51 C.).

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.

15760-35-7, name is 3-Methylenecyclobutanecarbonitrile, belongs to nitriles-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. Recommanded Product: 15760-35-7

3 -oxocyclobutanecarbonitrile [1266] A mixture of 3-methylenecyclobutanecarbonitrile (9.39 g, 101 mmol), dichloromethane (200 mL), water (300 mL), acetonitrile (200 mL), and ruthenium(III) chloride hydrate (0.500 g, 2.218 mmol) was cooled to <5 C, followed by portionwise addition of sodium periodate (88 g, 413 mmol) at <20 C, and stirred for 10 minutes. The mixture was diluted with dichloromethane and partitioned. The organic phase was filtered through a silica pad, dried ( a2S04), filtered, concentrated, and passed through a silica plug again, eluting with 200 mL dichloromethane to provide Example 125A (8.21 g, 86 mmol, 86 % yield) as a white solid. XH NMR (300 MHz, CDC13) ? 3.60 - 3.22 (m, 5H). The synthetic route of 15760-35-7 has been constantly updated, and we look forward to future research findings. Reference:
Patent; ABBVIE INC.; BAYBURT, Erol K.; CLAPHAM, Bruce; COX, Phil B.; DAANEN, Jerome F.; GOMTSYAN, Arthur; KORT, Michael E.; KYM, Philip R.; VOIGHT, Eric A.; SCHMIDT, Robert G.; DART, Michael J.; GFESSER, Gregory; WO2013/62964; (2013); A2;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

15760-35-7, The chemical industry reduces the impact on the environment during synthesis 15760-35-7, name is 3-Methylenecyclobutanecarbonitrile, I believe this compound will play a more active role in future production and life.

Sodium periodate (43.0 mmol, 9.20 g) was added portion-wise to a solution of 3- methylenecyclobutanecarbonitrile (21.5 mmol, 2.00 g) and ruthenium trichloride (0.47 mmol, 98 mg) in (0880) dichloromethane : acetonitrile : water (1:1:1.5; 175 mL) . The resulting suspension was vigorously stirred (0881) overnight. The organic phase was separated then the aqueous phase was further extracted with dichloromethane (3 x 50 mL) . The combined organic extracts were dried (MgSOi) then passed through a silica plug. The solvents were removed under reduced pressure to give the title compound as a dark solid (1.58 g, 74%).

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

Reference:
Patent; ONO PHARMACEUTICAL CO., LTD.; SAITO, Tetsuji; HIGASHINO, Masato; KAWAHARADA, Soichi; LEWIS, Arwel; CHAMBERS, Mark Stuart; RAE, Alastair; HIRST, Kim Louise; HARTLEY, Charles David; WO2015/115673; (2015); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts