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Chemical Structure| 4774-14-5 Chemical Structure| 4774-14-5
Chemical Structure| 4774-14-5

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CAS No.: 4774-14-5

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Product Details of 2,6-Dichloropyrazine

CAS No. :4774-14-5
Formula : C4H2Cl2N2
M.W : 148.98
SMILES Code : ClC1=CN=CC(Cl)=N1
MDL No. :MFCD00006125
InChI Key :LSEAAPGIZCDEEH-UHFFFAOYSA-N
Pubchem ID :78504

Safety of 2,6-Dichloropyrazine

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Application In Synthesis of 2,6-Dichloropyrazine

* 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.

  • Upstream synthesis route of [ 4774-14-5 ]
  • Downstream synthetic route of [ 4774-14-5 ]

[ 4774-14-5 ] Synthesis Path-Upstream   1~1

  • 1
  • [ 4774-14-5 ]
  • [ 77287-34-4 ]
  • [ 312736-50-8 ]
YieldReaction ConditionsOperation in experiment
36% at 20 - 90℃; for 14 h; To a mixture of 2,6-dichloropyrazine (11.0 g, 73.8 mmol) and formamide (58.6 mL, 1,476 mmol) was added dropwise sodium persulfate (17.1 g, 71.7 mmol). The reaction mixture was stirred at 90 for 2 h and was further stirred at rt for 12 h. After dilution with water, the mixture was extracted with isopropanol/chloroform (1/3) and washed with brine. The organic layer was dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by column chromatography (70percent n-hexane/EtOAc) to afford 3,5-dichloropyrazin-2-carboxamide (5.06 g, 36percent) as an oil.
36% at 90℃; 107241 2,6-Dichloropyrazine (55 g, 0.37 mol) and formamide (300 mL) were combined and heatedto 90 °C. Sodium persulfate (86.7 g, 0.36 mol) was added to the mixture at 90 °C in portions (1 g)20-3 0 second intervals. An exotherm was observed and the color of the mixture turned from yellowto dark red/brown. The mixture was stirred at 90 °C for 2 h and then cooled to room temperature.The mixture was diluted with water (500 mL) and filtered. The filtrate layers were separated. Theaqueous layer was extracted with IPAchloroform (1/3, 3 x 750 mL). The combined organic layers were dried over sodium sulfate and concentrated under vacuum to afford a viscous oil. The oil was purified by silica gel chromatography (0 to 100percent EtOAc in hexanes) to provide the title product as a colorless solid (25 g, 36percent yield). ‘HNMR (400 IVIHz, DMSO-d6): ppm 8.87 (s, 1H), 8.18 (br. s.,1H), 8.01 (br. s., 1H).
36% at 90℃; for 2 h; 2,6-Dichloropyrazine (55 g, 0.37 mol) and formamide (300 mL) were combined and heated to 90° C. Sodium persulfate (86.7 g, 0.36 mol) was added to the mixture at 90° C. in Ig portions at 20-30 seconds intervals.
An exotherm was observed and the color of the mixture turned from yellow to dark red/brown.
The mixture was stirred at 90° C. for 2 h and then cooled to room temperature.
The mixture was diluted with water (500 mL) and filtered.
The filtrate layers were separated.
The aqueous layer was extracted with IPA:chloroform (1:3, 3*750 mL).
The combined organic layers were dried over sodium sulfate and concentrated under vacuum to afford a viscous oil.
The oil was purified by silica gel chromatography (0 to 100percent ethyl acetate in hexanes) to provide the title product as a colorless solid (25 g, 36percent yield).
References: [1] Organic Letters, 2013, vol. 15, # 9, p. 2156 - 2159.
[2] Patent: WO2016/6975, 2016, A2, . Location in patent: Paragraph 457-459.
[3] Patent: KR2016/7347, 2016, A, . Location in patent: Paragraph 0359; 0360; 0361; 0362.
[4] Patent: WO2018/22992, 2018, A1, . Location in patent: Paragraph 0723; 0724.
[5] Patent: US2018/72743, 2018, A1, . Location in patent: Paragraph 1328-1329.
 

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