There will be a HazMat fee per item when shipping a dangerous goods. The HazMat fee will be charged to your UPS/DHL/FedEx collect account or added to the invoice unless the package is shipped via Ground service. Ship by air in Excepted Quantity (each bottle), which is up to 1g/1mL for class 6.1 packing group I or II, and up to 25g/25ml for all other HazMat items.
Type
HazMat fee for 500 gram (Estimated)
Excepted Quantity
USD 0.00
Limited Quantity
USD 15-60
Inaccessible (Haz class 6.1), Domestic
USD 80+
Inaccessible (Haz class 6.1), International
USD 150+
Accessible (Haz class 3, 4, 5 or 8), Domestic
USD 100+
Accessible (Haz class 3, 4, 5 or 8), International
USD 200+
Structure of 109-08-0 * Storage: {[proInfo.prStorage]}
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Reference：
[1] Chemistry of Heterocyclic Compounds (New York, NY, United States), 1993, vol. 29, # 11, p. 1308 - 1315[2] Khimiya Geterotsiklicheskikh Soedinenii, 1993, # 11, p. 1516 - 1525
6
[ 110-85-0 ]
[ 290-37-9 ]
[ 109-08-0 ]
[ 13925-00-3 ]
[ 109-97-7 ]
Reference：
[1] Chemistry of Heterocyclic Compounds (New York, NY, United States), 1993, vol. 29, # 11, p. 1308 - 1315[2] Khimiya Geterotsiklicheskikh Soedinenii, 1993, # 11, p. 1516 - 1525
[3] Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation), 1990, vol. 39, # 7.1, p. 1340 - 1345[4] Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, 1990, # 7, p. 1483 - 1488
[5] Chemistry of Heterocyclic Compounds (New York, NY, United States), 1993, vol. 29, # 11, p. 1308 - 1315[6] Khimiya Geterotsiklicheskikh Soedinenii, 1993, # 11, p. 1516 - 1525
7
[ 107-15-3 ]
[ 290-37-9 ]
[ 109-08-0 ]
[ 13925-00-3 ]
Reference：
[1] Chemistry of Heterocyclic Compounds (New York, NY, United States), 1993, vol. 29, # 11, p. 1308 - 1315[2] Khimiya Geterotsiklicheskikh Soedinenii, 1993, # 11, p. 1516 - 1525
[3] Chemistry of Heterocyclic Compounds (New York, NY, United States), 1993, vol. 29, # 11, p. 1308 - 1315[4] Khimiya Geterotsiklicheskikh Soedinenii, 1993, # 11, p. 1516 - 1525
8
[ 56-41-7 ]
[ 56-87-1 ]
[ 131543-46-9 ]
[ 290-37-9 ]
[ 109-08-0 ]
[ 13925-00-3 ]
Reference：
[1] Journal of Agricultural and Food Chemistry, 2010, vol. 58, # 4, p. 2470 - 2478
9
[ 56-87-1 ]
[ 50-99-7 ]
[ 109-08-0 ]
[ 5910-89-4 ]
[ 13925-00-3 ]
[ 13360-65-1 ]
[ 15707-23-0 ]
Reference：
[1] Journal of Agricultural and Food Chemistry, 2015, vol. 63, # 22, p. 5364 - 5372
10
[ 110-85-0 ]
[ 288-32-4 ]
[ 290-37-9 ]
[ 616-47-7 ]
[ 109-08-0 ]
[ 13925-00-3 ]
[ 693-98-1 ]
Reference：
[1] Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation), 1990, vol. 39, # 7.1, p. 1340 - 1345[2] Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, 1990, # 7, p. 1483 - 1488
Reference：
[1] Chemistry of Heterocyclic Compounds (New York, NY, United States), 1993, vol. 29, # 11, p. 1308 - 1315[2] Khimiya Geterotsiklicheskikh Soedinenii, 1993, # 11, p. 1516 - 1525
16
[ 56-45-1 ]
[ 290-37-9 ]
[ 109-08-0 ]
[ 13925-00-3 ]
[ 13925-03-6 ]
Reference：
[1] Journal of Agricultural and Food Chemistry, 1999, vol. 47, # 10, p. 4332 - 4335
17
[ 56-87-1 ]
[ 50-99-7 ]
[ 290-37-9 ]
[ 109-08-0 ]
[ 123-32-0 ]
[ 5910-89-4 ]
[ 22047-25-2 ]
[ 13360-65-1 ]
[ 108-50-9 ]
[ 14667-55-1 ]
[ 13925-07-0 ]
[ 13360-64-0 ]
Reference：
[1] Journal of Agricultural and Food Chemistry, 2010, vol. 58, # 4, p. 2470 - 2478
18
[ 56-45-1 ]
[ 56-87-1 ]
[ 50-99-7 ]
[ 290-37-9 ]
[ 109-08-0 ]
[ 123-32-0 ]
[ 5910-89-4 ]
[ 22047-25-2 ]
[ 13360-65-1 ]
[ 108-50-9 ]
[ 14667-55-1 ]
[ 13925-03-6 ]
[ 13360-64-0 ]
Reference：
[1] Journal of Agricultural and Food Chemistry, 2010, vol. 58, # 4, p. 2470 - 2478
19
[ 109-08-0 ]
[ 95-58-9 ]
Yield
Reaction Conditions
Operation in experiment
53%
With pyridine In tetrachloromethane
(i) Gaseous chlorine was passed into carbon tetrachloride (67 ml) for 30 minutes. The resulting yellow solution was added dropwise, over 30 minutes, to a stirred solution of pyridine (4.8 ml) and 2-methylpyrazine (5 g) in carbon tetrachloride (125 ml). The reaction was purged with nitrogen and volatile material was removed by evaporation. The resultant brown oil was purified by chromatography on silica gel, eluding with dichloromethane, to give 2-chloro-3-methylpyrazine as a brown oil (3.62 g, 53percent); 1 H NMR (d6 -DMSO): 6.59 (s,2H), 7.67 (d,1H), 7.94(d,1H); mass spectrum (+ve CI): 129 (M+H)+.
8.36 g
With hydrogenchloride; dihydrogen peroxide In water at 0 - 15℃;
(1) Dissolve 9.41 g (0.1 mol) of 2-methylpyrazine in 30.0percent of 182.30 g of hydrochloric acid (containing 1.5 mol of hydrogen chloride).Under stirring, the temperature was controlled at 0-15°C, and 25.32 g of a 25.0percent hydrogen peroxide solution was added dropwise.The reaction temperature was controlled at 0-15°C to make the reaction system chlorinated. The reaction was sampled at regular intervals and detected by high performance liquid chromatography.When it was detected that the mass of 2-methyl-3-chloropyrazine in the reaction system accounted for 73.5percent of the total organic matter mass in the reaction system,The reaction was terminated by adding 17.21 g (0.12 mol) of cuprous bromide to obtain a 2-methyl-3-chloropyrazine-containing solution; (2) Add 63.78 g of methylene chloride to the feed solution, stir and extract for 2 hours, and let stand for 1 hour.Take the organic phase and allow it to cool down to -15°C to -5°C to allow solids to be analyzed from the organic phase.8.36 g of the resulting fixative is 2-methyl-3-chloropyrazine,After calculation, the yield was 65.5percent, and the main containment was 97.8percent.
Reference：
[1] Patent: US5861401, 1999, A,
[2] Patent: CN107954913, 2018, A, . Location in patent: Paragraph 0021
20
[ 109-08-0 ]
[ 19847-12-2 ]
Reference：
[1] Patent: US4496729, 1985, A,
[2] Applied Catalysis A: General, 2012, vol. 443-444, p. 111 - 118
[3] Journal of the Chemical Society, Faraday Transactions 1: Physical Chemistry in Condensed Phases, 1988, vol. 84, # 7, p. 2397 - 2408
[4] Chemical Communications, 2001, # 20, p. 2088 - 2089
[5] Patent: US4778890, 1988, A,
[6] Patent: US4778890, 1988, A,
[7] Journal of Chemical Sciences, 2014, vol. 126, # 2, p. 487 - 498
[8] Catalysis Science and Technology, 2014, vol. 4, # 9, p. 3306 - 3316
[9] Catalysis Communications, 2018, vol. 108, p. 17 - 22
21
[ 109-08-0 ]
[ 290-37-9 ]
[ 19847-12-2 ]
[ 98-96-4 ]
Reference：
[1] Chemical Communications, 2011, vol. 47, # 29, p. 8394 - 8396
22
[ 107-15-3 ]
[ 56-81-5 ]
[ 290-37-9 ]
[ 109-08-0 ]
[ 123-32-0 ]
[ 5910-89-4 ]
[ 6705-33-5 ]
[ 108-50-9 ]
[ 5780-66-5 ]
Reference：
[1] Kinetics and Catalysis, 2016, vol. 57, # 5, p. 602 - 609[2] Kinet. Katal., 2016, vol. 57, # 5, p. 607 - 614,8
23
[ 109-08-0 ]
[ 6705-33-5 ]
Reference：
[1] Journal of Organic Chemistry, 1958, vol. 23, p. 1603,1605
[2] Yakugaku Zasshi, 1959, vol. 79, p. 1273,1276[3] Chem.Abstr., 1960, p. 4607
24
[ 107-15-3 ]
[ 56-81-5 ]
[ 109-08-0 ]
[ 6705-33-5 ]
Reference：
[1] Applied Catalysis A: General, 2014, vol. 469, p. 398 - 409
[2] Journal of Chemical Sciences, 2014, vol. 126, # 2, p. 387 - 393
25
[ 109-08-0 ]
[ 98-97-5 ]
Reference：
[1] Chemistry of Heterocyclic Compounds (New York, NY, United States), 1991, vol. 27, # 7, p. 768 - 771[2] Khimiya Geterotsiklicheskikh Soedinenii, 1991, # 7, p. 959 - 962
[3] Chemistry of Heterocyclic Compounds (New York, NY, United States), 1995, vol. 31, # 1, p. 80 - 85[4] Khimiya Geterotsiklicheskikh Soedinenii, 1995, # 1, p. 90 - 96
[5] Synthetic Communications, 2003, vol. 33, # 3, p. 475 - 480
[6] Bioorganic and Medicinal Chemistry Letters, 2000, vol. 10, # 15, p. 1723 - 1727
[7] Journal fuer Praktische Chemie (Leipzig), 1895, vol. <2>51, p. 464
[8] Journal of Organic Chemistry, 1959, vol. 24, p. 691
[9] J. Appl. Chem. USSR (Engl. Transl.), 1992, vol. 65, # 9.2, p. 1696 - 1699[10] Zhurnal Prikladnoi Khimii (Sankt-Peterburg, Russian Federation), 1992, vol. 65, # 9, p. 2075 - 2078
[11] Organic Process Research and Development, 1999, vol. 3, # 6, p. 455 - 459
[12] Organic Process Research and Development, 1999, vol. 3, # 2, p. 109 - 113
[13] International Journal of Molecular Sciences, 2018, vol. 19, # 10,
26
[ 109-08-0 ]
[ 25594-37-0 ]
[ 31396-35-7 ]
[ 98-97-5 ]
[ 5780-66-5 ]
[ 874-54-4 ]
[ 32046-09-6 ]
Reference：
[1] Chemistry - A European Journal, 2008, vol. 14, # 8, p. 2340 - 2348
[2] Chemistry - A European Journal, 2008, vol. 14, # 8, p. 2340 - 2348
27
[ 109-08-0 ]
[ 25594-37-0 ]
[ 31396-35-7 ]
[ 98-97-5 ]
[ 874-54-4 ]
[ 32046-09-6 ]
Reference：
[1] Chemistry - A European Journal, 2008, vol. 14, # 8, p. 2340 - 2348
Reference：
[1] Chemistry - A European Journal, 2008, vol. 14, # 8, p. 2340 - 2348
[2] Chemistry - A European Journal, 2008, vol. 14, # 8, p. 2340 - 2348
41
[ 56-87-1 ]
[ 78-98-8 ]
[ 109-08-0 ]
[ 123-32-0 ]
[ 5910-89-4 ]
[ 13360-65-1 ]
[ 108-50-9 ]
[ 55138-72-2 ]
[ 55138-74-4 ]
[ 14667-55-1 ]
[ 13925-07-0 ]
Reference：
[1] Journal of Agricultural and Food Chemistry, 2010, vol. 58, # 4, p. 2470 - 2478
42
[ 134276-45-2 ]
[ 78-98-8 ]
[ 109-08-0 ]
[ 123-32-0 ]
[ 5910-89-4 ]
[ 13360-65-1 ]
[ 108-50-9 ]
[ 55138-74-4 ]
[ 14667-55-1 ]
[ 80935-98-4 ]
[ 13925-07-0 ]
[ 15707-34-3 ]
Reference：
[1] Journal of Agricultural and Food Chemistry, 2010, vol. 58, # 4, p. 2470 - 2478
43
[ 410538-35-1 ]
[ 78-98-8 ]
[ 109-08-0 ]
[ 123-32-0 ]
[ 5910-89-4 ]
[ 1124-11-4 ]
[ 13360-65-1 ]
[ 108-50-9 ]
[ 14667-55-1 ]
[ 80935-98-4 ]
[ 13925-07-0 ]
[ 15707-34-3 ]
Reference：
[1] Journal of Agricultural and Food Chemistry, 2010, vol. 58, # 4, p. 2470 - 2478
44
[ 50-99-7 ]
[ 103404-72-4 ]
[ 290-37-9 ]
[ 109-08-0 ]
[ 123-32-0 ]
[ 5910-89-4 ]
[ 13360-65-1 ]
[ 108-50-9 ]
[ 14667-55-1 ]
[ 13925-03-6 ]
[ 13925-07-0 ]
[ 13360-64-0 ]
Reference：
[1] Journal of Agricultural and Food Chemistry, 2010, vol. 58, # 4, p. 2470 - 2478
45
[ 103404-72-4 ]
[ 78-98-8 ]
[ 109-08-0 ]
[ 123-32-0 ]
[ 5910-89-4 ]
[ 13360-65-1 ]
[ 108-50-9 ]
[ 14667-55-1 ]
[ 17398-16-2 ]
[ 13925-07-0 ]
[ 15707-34-3 ]
[ 18433-97-1 ]
Reference：
[1] Journal of Agricultural and Food Chemistry, 2010, vol. 58, # 4, p. 2470 - 2478
46
[ 50-99-7 ]
[ 275366-32-0 ]
[ 290-37-9 ]
[ 109-08-0 ]
[ 123-32-0 ]
[ 5910-89-4 ]
[ 13360-65-1 ]
[ 108-50-9 ]
[ 14667-55-1 ]
[ 13925-03-6 ]
[ 13925-07-0 ]
[ 13360-64-0 ]
Reference：
[1] Journal of Agricultural and Food Chemistry, 2010, vol. 58, # 4, p. 2470 - 2478
47
[ 275366-32-0 ]
[ 78-98-8 ]
[ 109-08-0 ]
[ 123-32-0 ]
[ 5910-89-4 ]
[ 13360-65-1 ]
[ 108-50-9 ]
[ 14667-55-1 ]
[ 80935-98-4 ]
[ 13925-07-0 ]
[ 22047-27-4 ]
[ 15707-34-3 ]
Reference：
[1] Journal of Agricultural and Food Chemistry, 2010, vol. 58, # 4, p. 2470 - 2478
48
[ 61-90-5 ]
[ 56-87-1 ]
[ 78-98-8 ]
[ 109-08-0 ]
[ 123-32-0 ]
[ 5910-89-4 ]
[ 1124-11-4 ]
[ 13360-65-1 ]
[ 108-50-9 ]
[ 55138-72-2 ]
[ 14667-55-1 ]
[ 13925-07-0 ]
Reference：
[1] Journal of Agricultural and Food Chemistry, 2010, vol. 58, # 4, p. 2470 - 2478
49
[ 56-87-1 ]
[ 50-99-7 ]
[ 290-37-9 ]
[ 109-08-0 ]
[ 123-32-0 ]
[ 5910-89-4 ]
[ 22047-25-2 ]
[ 13360-65-1 ]
[ 108-50-9 ]
[ 14667-55-1 ]
[ 13925-07-0 ]
[ 13360-64-0 ]
Reference：
[1] Journal of Agricultural and Food Chemistry, 2010, vol. 58, # 4, p. 2470 - 2478
50
[ 50-99-7 ]
[ 45234-02-4 ]
[ 290-37-9 ]
[ 109-08-0 ]
[ 123-32-0 ]
[ 5910-89-4 ]
[ 13360-65-1 ]
[ 108-50-9 ]
[ 14667-55-1 ]
[ 13925-07-0 ]
[ 13360-64-0 ]
[ 15707-34-3 ]
Reference：
[1] Journal of Agricultural and Food Chemistry, 2010, vol. 58, # 4, p. 2470 - 2478
51
[ 50-99-7 ]
[ 40719-58-2 ]
[ 290-37-9 ]
[ 109-08-0 ]
[ 123-32-0 ]
[ 5910-89-4 ]
[ 13360-65-1 ]
[ 108-50-9 ]
[ 14667-55-1 ]
[ 13925-03-6 ]
[ 13925-07-0 ]
[ 13360-64-0 ]
Reference：
[1] Journal of Agricultural and Food Chemistry, 2010, vol. 58, # 4, p. 2470 - 2478
52
[ 40719-58-2 ]
[ 78-98-8 ]
[ 109-08-0 ]
[ 123-32-0 ]
[ 5910-89-4 ]
[ 13360-65-1 ]
[ 108-50-9 ]
[ 14667-55-1 ]
[ 80935-98-4 ]
[ 13925-07-0 ]
[ 22047-26-3 ]
[ 15707-34-3 ]
Reference：
[1] Journal of Agricultural and Food Chemistry, 2010, vol. 58, # 4, p. 2470 - 2478
53
[ 78-98-8 ]
[ 109-08-0 ]
[ 123-32-0 ]
[ 5910-89-4 ]
[ 1124-11-4 ]
[ 13360-65-1 ]
[ 108-50-9 ]
[ 14667-55-1 ]
[ 80935-98-4 ]
[ 13925-07-0 ]
[ 15707-34-3 ]
Reference：
[1] Journal of Agricultural and Food Chemistry, 2010, vol. 58, # 4, p. 2470 - 2478
54
[ 56-41-7 ]
[ 56-87-1 ]
[ 78-98-8 ]
[ 109-08-0 ]
[ 123-32-0 ]
[ 5910-89-4 ]
[ 13360-65-1 ]
[ 108-50-9 ]
[ 14667-55-1 ]
[ 80935-98-4 ]
[ 13925-07-0 ]
[ 22047-26-3 ]
[ 15707-34-3 ]
Reference：
[1] Journal of Agricultural and Food Chemistry, 2010, vol. 58, # 4, p. 2470 - 2478
55
[ 56-87-1 ]
[ 56-86-0 ]
[ 50-99-7 ]
[ 290-37-9 ]
[ 109-08-0 ]
[ 123-32-0 ]
[ 5910-89-4 ]
[ 13360-65-1 ]
[ 108-50-9 ]
[ 14667-55-1 ]
[ 13925-03-6 ]
[ 13925-07-0 ]
[ 13360-64-0 ]
Reference：
[1] Journal of Agricultural and Food Chemistry, 2010, vol. 58, # 4, p. 2470 - 2478
56
[ 56-87-1 ]
[ 63-91-2 ]
[ 78-98-8 ]
[ 109-08-0 ]
[ 123-32-0 ]
[ 5910-89-4 ]
[ 13360-65-1 ]
[ 108-50-9 ]
[ 55138-72-2 ]
[ 14667-55-1 ]
[ 17398-16-2 ]
[ 13925-07-0 ]
[ 15707-34-3 ]
Reference：
[1] Journal of Agricultural and Food Chemistry, 2010, vol. 58, # 4, p. 2470 - 2478
57
[ 56-87-1 ]
[ 56-40-6 ]
[ 78-98-8 ]
[ 109-08-0 ]
[ 123-32-0 ]
[ 5910-89-4 ]
[ 1124-11-4 ]
[ 13360-65-1 ]
[ 108-50-9 ]
[ 14667-55-1 ]
[ 13925-07-0 ]
[ 22047-26-3 ]
[ 15707-34-3 ]
Reference：
[1] Journal of Agricultural and Food Chemistry, 2010, vol. 58, # 4, p. 2470 - 2478
58
[ 90210-53-0 ]
[ 290-37-9 ]
[ 109-08-0 ]
[ 245-44-3 ]
[ 28217-95-0 ]
Reference：
[1] Synthesis, 1983, # 12, p. 1037 - 1040
59
[ 56-87-1 ]
[ 50-99-7 ]
[ 109-08-0 ]
[ 5910-89-4 ]
[ 15707-23-0 ]
Reference：
[1] Journal of Agricultural and Food Chemistry, 2015, vol. 63, # 22, p. 5364 - 5372
60
[ 56-87-1 ]
[ 50-99-7 ]
[ 109-08-0 ]
[ 5910-89-4 ]
[ 13925-00-3 ]
[ 13360-65-1 ]
[ 15707-23-0 ]
Reference：
[1] Journal of Agricultural and Food Chemistry, 2015, vol. 63, # 22, p. 5364 - 5372
61
[ 123-84-2 ]
[ 290-37-9 ]
[ 109-08-0 ]
[ 123-32-0 ]
[ 13925-00-3 ]
[ 693-98-1 ]
[ 15707-23-0 ]
Reference：
[1] Chemistry of Heterocyclic Compounds (New York, NY, United States), 1993, vol. 29, # 11, p. 1308 - 1315[2] Khimiya Geterotsiklicheskikh Soedinenii, 1993, # 11, p. 1516 - 1525
In a 500 mL reactor, 94.1 g (1 mol) of 2-methylpyrazine was added.0.2 g (0.0016 mol) of ferrous chloride, and 225 g (1.99 mol) of hydrogen peroxide having a mass concentration of 30% was added dropwise at 30 C.After the completion of the dropwise addition for 4 hours, the temperature was raised to 50 C, and 40 g (2.35 mol) of ammonia gas was introduced. After the completion of the ammonia gas, the temperature was maintained for 7 hours.After cooling to 10 C, the crude product was filtered.The crude product was recrystallized from 3 times by weight of water to give 117 g of the desired pyrazinamide in a yield of 95%.
2-Methoxybenzonitrile (3.0 g, 22.5 mmol) and 2-methylpyrazine (2.2 g, 23.0 mmol) were dissolved in an ice-water bathIn dry tetrahydrofuran (50 mL) and stirred under nitrogen for 1.5 hours.under this conditionLithium diisopropylamide (23 mL, 45.06 mmol, tetrahydrofuran solution) was slowly added, and the addition was complete and the temperature was raised to 40C and stirring was continued for 3 hours.The reaction solution was cooled to ambient temperature, quenched with ammonium chloride solution, extracted with ethyl acetate (50 mL × 3), dried over anhydrous sodium sulfate, and filtered.The organic layer was concentrated under reduced pressure and the residue was purified by flash column chromatography (petroleum ether/ethyl acetate = 1/1) to give compound 5.1 as a yellow solid.Body (2.2 g, yield: 39%).
6-(3,4,5-trimethoxyphenyl)[5H]pyrrolo[2,3-b]pyrazine[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
50%
Stage #1: 2-Methylpyrazine With lithium diisopropyl amide In tetrahydrofuran at -40℃; for 0.5h;
Stage #2: 3,4,5-trimethoxybenzonitrile In tetrahydrofuran at -40 - 20℃; Further stages.;
Under an argon gas flow, diisopropylamine (7.70 g) was dissolved in tetrahydrofuran (50 ml), followed by stirring at -78C. A solution of 1.52 M n-butyl lithium in hexane (50 ml) was slowly added dropwise. After the dropwise addition, the mixture was slowly returned to room temperature over 30 minutes and cooled to -78C again to prepare lithium diisopropylamide. To this was added 2-methylpyrazine (4.29 g), the solution was stirred at 0C for 30 minutes and benzonitrile (4.7 g) was slowly added dropwise so that the inner temperature does not exceed 15C. After stirring at 0C for 90 minutes, lithium diisopropylamide was added dropwise, followed by stirring at 40C for 3 hours. The reaction solution was mixed with ice water, extracted with chloroform, washed with saturated brine, dried and then concentrated. The residue was purified by silica gel column chromatography (chloroform:n-hexane = 20:1) to obtain the objective product (2.2 g).
With mixed oxide-ZnAl catalyst In water at 400℃; Inert atmosphere;
The chemicals used were both purchased from Sigma Aldrich: propylene glycol 99% purity and ethylenediamine for synthesis, which was purified by distillation prior to the reactions. The reactions for 2-methylpyrazine synthesis using ZnAl; NiAl; CoAl mixed oxides as catalytic materials were performed in a fixed bed reactor made of heat resistant glass (230 mm height - 15 mm diameter). The middle part of the reactor, containing the catalyst bed (11 mm height, dp=60 mesh), was heated at the desired temperature. Prior to the reactions, the catalyst was activated at 400 °C for 2 h in a flow of gas mixture (H2/Ar=1/1, vol.). The liquid reactants were introduced with a controlled feed rate (1 mL·h-1) from the top side of the reactor tube, using a peristaltic pump. The aqueous reaction mixture was prepared by diluting propylene glycol and ethylenediamine (mole ratio=1/1) in distilled water (50% vol.). The water was used for reducing the viscosity of the mixture. The inert carrier gas used was pure argon, at a flow rate of 15 mL·min-1.
In water; at 375℃; under 760.051 Torr; for 6h;Inert atmosphere; Flow reactor;
The dehydrocyclization activities of Zn?Cr?Ocatalysts calcined at different temperatures were performedat 375°C and atmospheric pressure in a fixedbedvertical quartz reactor (i.d = 8 mm, length =450 mm) placed in a two zone furnace operated in adown flow mode. In the first zone maintained at300°C the reaction mixture was preheated whereas inthe second zone containing the catalyst bed the reactortemperature was set at 375°C. Temperatures in theboth zones were monitored by a temperature controller-cum-programmer using a K-type thermocouple.Glycerol (Fluka) and EDA (SDFCL, India) wereused. Nitrogen (IOLAR-I grade, BOC, India) wasused as a carrier gas. The catalytic activities were measured using ?18/+23 sieved (BSS) particles. The carbonmass balance was done based on the inlet and outletconcentration of the organic moiety. Prior to thereaction, the calcined catalyst (about 0.2 g) wasreduced in a flow of 5percent H2 and 95percent Ar (30 mL min?1)at 400°C for 5 h. The catalytic activities were measuredunder strict kinetic control. An aqueous glycerol solution(20 wtpercent in H2O) was used with a glycerol to EDAmole ratio of 1 :1 , at a flow rate of 5 mL h?1 (10 mmolglycerol + 10 mmol EDA + 200 mmol H2O), alongwith N2 as a carrier gas at a flow rate of 1800 mL h?1.The feed mixture mole ratio is glycerol : EDA : H2O :N2= 1 : 1 : 20 : 8. The product mixture was analyzed bygas chromatograph (Shimadzu, GC-17A) via a flameionization detector (FID) using a ZB-5 capillary columnat a ramping rate of 10°C min?1 from 60 to280°C. The mass balance for all the measurements was>95percent. The samples were analyzed by GC-MS(QP5050A Shimadzu) using a ZB-5 capillary columnwith EI mode.
General procedure: The preparation of co-crystals 1e3 was conducted through solutioncrystallization experiments. Co-crystal 1 was obtained usingthe following procedure: MP (0.25 mmol, 23.5 mg) and <strong>[636-46-4]4-HIPA</strong>(0.5 mmol, 91.1 mg), in a 1:2 stoichiometric ratio, were dissolvedin separate beakers in 15 mL of methanol, and subsequently combinedtogether. The resulting solutionwas left to evaporate at roomtemperature. Two weeks later, colorless block-like co-crystals of 1were obtained. (yield87%, based on 2-methylpyrazine). Elementalanalysis for co-crystal 1, Anal. Calcd. (%): C, 55.03; H, 3.96; N, 6.11.Found: C, 54.96; H, 3.98; N, 6.17. IR (KBr pellet, cm1): 3435, 2918,2517,1682,1588,1441,1400,1360,1281,1244,1225,1174,1067,1040,934, 806, 775, 690, 633, 566, 519.
With 1,10-Phenanthroline; potassium <i>tert</i>-butylate; iron(II) acetate In toluene at 140℃; for 24h; Inert atmosphere; chemoselective reaction;
71%
With bromopentacarbonylmanganese(I); potassium <i>tert</i>-butylate; 1-(pyridin-2-yl)-2-(1-(pyridin-2-yl)ethylidene)hydrazine In <i>tert</i>-butyl alcohol at 140℃; for 16h; Inert atmosphere; Schlenk technique;
71%
With 1,10-Phenanthroline; potassium hydroxide; nickel dibromide In toluene at 140℃; for 36h; Schlenk technique; Inert atmosphere;
To a solution of 2M LDA in THF/hexane/ethylbenzene (4.3 ml, 8.60 mmol) in dry THF (5 ml) cooled to -78C under inert atmosphere was added methylpyrazine (0.40 g, 4.25 mmol). The RM was stirred for 15 min then <strong>[57267-03-5]ethyl 2,2,2-triethoxyacetate</strong> (1.03 ml, 4.68 mmol) was added. The solution was allowed to warm to RT and stirred for 16 h. The RM was poured into 1M HC1 and stirred for 1 h. The mixture was neutralized with NaHC03 solution and extracted three times with DCM. The combined organics were washed with brine, dried over Na2S04, filtered and evaporated. The crude was purified by FCC (0 - 90 % EtOAc in DCM) to give the title compound as an orange solid. Y = 87 %. NMR (300 MHz, chloroform-) delta 13.01 (s, 1H), 8.60 (d, J= 2 Hz, 1H), 8.49 (d, J= 3 Hz, 1H), 8.45 - 8.41 (m, 1H), 6.66 (s, 1H), 4.40 (q, J= 7 Hz, 2H), 1.42 (t, J= 7 Hz, 3H)
With chlorine; triethylamine; In 1,2-dichloro-ethane; at 45 - 60℃; under 150.015 - 225.023 Torr; for 4.5h;Large scale;
100L enamel reaction kettle, equipped with material dropping pipe (connected with metering pump), equipped with chlorine gas introduction pipe (connected with chlorine gas automatic control system), automatic pressure control system, temperature detection chain control system. Add 96kg of solvent dichloroethane and 1kg of triethylamine to the reaction kettle and start stirring, then pass chlorine gas, and set the pressure in the kettle to be automatically controlled at 0.02-0.03MPa for 20-30 minutes. Then start feeding with a metering pump at a rate of 5kg/h (according to 10kg of methylpyrazine mixed with 10kg of dichloroethane to be used evenly), the reaction exotherm is obvious, the reaction temperature is controlled at 45 ~ 60 C , the temperature is higher than 60C. The feeding system is automatically cut off at (if necessary, the water flow can be manually controlled to lower the temperature), the beating is completed in about 4 hours, and then the reaction is continued for 30 minutes at a pressure of 0.02 ~ 0.03MPa. Then lower the temperature to 30-40C, introduce the residual chlorine gas in the reaction kettle into the lye spray absorption tower to absorb, the remaining reaction liquid in the kettle is pressed into the dichloroethane turnover tank with nitrogen through the pipeline filter (containing chlorine gas for recycling), the reaction kettle The remaining chloropyrazine hydrochloride solid is dissolved in 30Kg of water first, and then neutralized with 30% alkaline solution to pH 6-7, and then separated into layers to obtain crude chloropyrazine, about 12Kg, content about 92 % Is directly used for the next reaction.
N-methyl-2-phenyl-2-trifluoromethylbenzimidazoline[ No CAS ]
[ 61655-67-2 ]
Yield
Reaction Conditions
Operation in experiment
63 %Spectr.
With [2,2]bipyridinyl; copper(l) iodide; potassium carbonate In benzonitrile at 90℃; for 48h;
General procedure of trifluoromethylation (Procedure I)
General procedure: Aryl iodide 1 (0.1 mmol), trifluoromethylbenzimidazolidine 2 (56 mg, 0.2 mmol), CuI (3.8 mg, 0.02 mmol), 2,2’-bipyridine (12.5 mg, 0.08 mmol), and potassium carbonate (55.6 mg, 0.4 mmol) were mixed in benzonitrile (1.0 mL), and the mixture warmed at 90 °C. After 48 h, hexafluorobenzene was added as an internal standard and a 19F NMR spectrum recorded for the calculation of the NMR yield. Then the crude products were purified by preparative TLC to give the trifluoromethylated products 3.
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