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[ CAS No. 408538-29-4 ] {[proInfo.proName]}

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Chemical Structure| 408538-29-4
Chemical Structure| 408538-29-4
Structure of 408538-29-4 * Storage: {[proInfo.prStorage]}
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Product Details of [ 408538-29-4 ]

CAS No. :408538-29-4 MDL No. :MFCD07375051
Formula : C6H4ClN3 Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W : 153.57 Pubchem ID :-
Synonyms :

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Application In Synthesis of [ 408538-29-4 ]

* 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.

  • Downstream synthetic route of [ 408538-29-4 ]

[ 408538-29-4 ] Synthesis Path-Downstream   1~9

  • 2
  • [ 75806-86-9 ]
  • [ 408538-29-4 ]
  • 3
  • [ 21427-61-2 ]
  • [ 408538-29-4 ]
  • 4
  • [ 181123-11-5 ]
  • [ 408538-29-4 ]
  • [ 27330-34-3 ]
YieldReaction ConditionsOperation in experiment
With iron; acetic acid; at 80℃; for 0.5h; Step 2: A 250 mL round-bottom flask was charged with the iron powder (15.6 g, 0.3 mol), AcOH (80 mL) and heated to 80 C (oil bath) under N2. To this mixture, was added a solution of nitrocyanopyridine (10 g, 0.055 mmol) in AcOH (80 mL) via addition funnel and stirred at 80 C for an additional 30 min after the addition. The reaction was subsequently cooled to room temperature, diluted with EtOAc, filtered through a pad of Celite and concentrated under reduced pressure. The residue was dissolved in EtOAc and washed with 3 N NaOH and brine, dried over MgSO4, and concentrated under reduced pressure and to afford the crude 3-amino-2-cyano-5-chloropyridine along with the 2-amide (7.7 g) which was used directly for the next step : MS 154.0 (M+H).
With iron; acetic acid; at 80℃; for 0.75h; A 250 mL round-bottom flask with a magnetic stir bar was charged with iron powder (15 6 g, 0 3 mol) in acetic acid (80 mL) and heated to 80 0C (oil bath) under N2 To this mixture was added slowly the above nitrocyanopyridine (10 g, 55 mmol) from step 1 in acetic acid (80 mL) via dropping funnel over 15 minutes The mixture was stirred at 80 0C for another 30 mm after the addition After cooling, the reaction mixture was diluted with EtOAc, filtered through celite and the solvent evaporated in vacuo The residue was dissolved in EtOAc and washed with 3 N NaOH, brine, dried over MgSO4, and concentrated in vacuo to afford a 4 1 mixture (7 7 g) of S-amino^-cyano-delta-chloropy?dine (major) and the 2-amiotade The mixture was used directly for the next step MS (ES) (M+H) + expected 154 0, found 154 0
  • 5
  • [ 408538-29-4 ]
  • [ 32333-53-2 ]
  • C13H6Cl2F3N3O2S [ No CAS ]
  • C13H8Cl2F3N3O3S [ No CAS ]
YieldReaction ConditionsOperation in experiment
With pyridine at 70℃; for 5h; 121.3 Step 3: A 500 mL round-bottom flask was charged with the above 3-amino-2-cyano-5-chloropyridine (7.7 g, 50 mmol), 4-CI-3-trifluoromethyl- benzenesulfonyl chloride (28 g, 100 mmol), and pyridine (50 mL). The resultant solution was heated to 70 °C and stirred for 5 h. The pyridine was removed in vacuo and EtOH (80%, 260 mL) was added, followed by NaOH (30 g, 0.75 mol). The mixture was heated at reflux for 12 h. The solvent was subsequently removed in vacuo and ice (100 g) was added and the pH adjusted to 2-3 with cone HCI. The resultant aqueous solution was extracted with EtOAc, washed with brine, dried over MgSO4, and concentrated under reduced pressure. The EPO resultant light yellow solid was further crystallized from EtOAc/hexane (1 :1) to afford 5-chloro-3-(4-chloro-3-(trifluoromethyl)phenylsulfonamido)picolinic acid as white needles (10 g, 44% overall): 1H NMR (400 MHz, CDCI3) δ 10. 80 (s, 1 H), 8.23 (m, 3H), 8.00 (d, 1 H), 7.63 (d, 1 H); MS (ES) 415.0 (M+H).
  • 6
  • [ 408538-29-4 ]
  • [ 32333-53-2 ]
  • C13H6Cl2F3N3O2S [ No CAS ]
YieldReaction ConditionsOperation in experiment
With pyridine at 70℃; for 5h; 3 A 100 mL round-bottom flask was charged with the above 3-amιno-2-cyano-5-chloropyrιdιne mixture (7 7 g, 50 mmol), 4-chloro-3- trifluoromethylbenzenesulfonyl chloride (28 g, 100 mmol), and pyridine (50 mL). The resultant solution was heated to 70 "C and stirred for 5 hours. The pyridine was removed in vacuo and 80% aq. EtOH (260 mL) was added, followed by NaOH (30 g, 0.75 mol). The mixture was stirred under reflux for 12 hours. The solvent was subsequently removed in vacuo and ice (100 g) was added. The pH adjusted to 2-3 with cone. HCI. The resultant aqueous solution was extracted with EtOAc, washed with brine, dried over MgSO4, and concentrated in vacuo. The resulting light yellow solid was recrystallized from EtOAc/hexane ( 1 : 1 ) to afford the desired acid as white needles (10 g, 44% overall yield): 1H NMR (400 MHz, CDCI3) δ 10.80 (s, 1 H), 8.23 (m, 3H), 8.00 (d, 1 H), 7.63 (d, 1 H); MS (ES) (M+H)+ expected 415.0, found 415.0.
  • 7
  • [ 408538-29-4 ]
  • [ 27330-34-3 ]
YieldReaction ConditionsOperation in experiment
19 g With sulfuric acid; at 80℃; for 4h; 3-Amino-5-chloropicolinonitrile (25 g, 162.8 mmol) was added 80 mL of concentrated sulfuric acid and the resulting mixture was stirred at 80C for 4 hours. After cooled to room temperature, the resulting mixture was poured into ice cold water and the pH value was adjusted to 12 with saturated sodium hydroxide solution. The precipitated solid was collected by filtration and the filter cake was washed with water and dried in vacuo to give 19 g (77%) of the title compound as a yellow solid. MS (ESIpos): m/z = 172 (M+H)+. LC-MS [Method 2]: R, = 0.75 min.
  • 8
  • [ 408538-29-4 ]
  • [ 917757-12-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: sulfuric acid / 4 h / 80 °C 2: 48 h / 130 °C 3: N,N-dimethyl-formamide; sulfuryl dichloride / 2 h / Reflux
  • 9
  • [ 181123-11-5 ]
  • [ 408538-29-4 ]
YieldReaction ConditionsOperation in experiment
With iron; acetic acid; at 20℃; for 5h; To a solution of <strong>[181123-11-5]5-chloro-3-nitropicolinonitrile</strong> (30 g, 163.4 mmol) in 500 mL of acetic acid were added iron powder (54.8 g, 980.6 mmol). The resulting mixture was stirred at room temperature for 5 hours. Upon completion of the reaction, water was added and the solid was removed by filtration. The filtrate was extracted with ethyl acetate and the combined organic layer was washed with water, brine and dried over anhydrous sodium sulfate. The solvent was removed in vacuo to give 30.0 g (crude) of the title compound as a brown solid. MS (ESIpos): m/z = 154 (M+H)+. LC-MS [Method 1]: Rt = 0.92 min.
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