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Structure of 24755-82-6

Chemical Structure| 24755-82-6

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Product Details of [ 24755-82-6 ]

CAS No. :24755-82-6
Formula : C13H11ClN2O2
M.W : 262.69
SMILES Code : O=C(C1=CN=C(C2=CC=CC=C2)N=C1Cl)OCC
MDL No. :MFCD01935974
InChI Key :VXWYTPARKVGWFX-UHFFFAOYSA-N
Pubchem ID :239537

Safety of [ 24755-82-6 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H315-H319-H335
Precautionary Statements:P264-P302+P352-P304+P340-P305+P351+P338-P332+P313-P337+P313

Application In Synthesis of [ 24755-82-6 ]

* 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 [ 24755-82-6 ]

[ 24755-82-6 ] Synthesis Path-Upstream   1~1

  • 1
  • [ 24755-82-6 ]
  • [ 85386-14-7 ]
YieldReaction ConditionsOperation in experiment
50%
Stage #1: With zinc In tetrahydrofuran at 60℃; for 1 h;
Stage #2: With acetic acid In tetrahydrofuran at 60℃; for 23 h;
In a round bottomed flask under argon atmosphere were successively added anhydrous ethanol(5 mL), sodium metal (0.426 g, 18.5 mmol), benzamidine hydrochloride (2.90 g, 18.5 mmol)and diethyl 2-(ethoxymethylene)malonate (4.0 g, 18.5 mmol). The reaction mixture was stirredat room temperature for 9 h, and then poured into ice. The precipitate was filtered, washedwith coldwater and recrystallized in EtOH-MeOH-CHCl3 (1:1:1) (45 mL), giving the ethyl4-hydroxy-2-phenylpyrimidine-5-carboxylate (8) as a white crystalline solid in 50percent yield. Thederivative 8 (1.2 g, 4.91 mmol) and POCl3 (9.8 g, 63.9 mmol) were refluxed at 100oC for 1 h. Theexcess of POCl3 was removed under vacuum, ice was added on the resulting solid into the reactionflask, followed by filtration and washing with cold water. The chloride compound 9, obtained as awhite amorphous solid in 98percent yield, was successively dehalogenated with zinc powder (0.176 g,2.69 mmol, 4 equiv) in anhydrous THF (2 mL). The reaction mixture was stirred at 60 °C for 1 h, andthen 5 drops of acetic acid were added to the reaction vessel. After stirring at 60 °C for 23 h, thereaction mixture was cooled to room temperature, followed by addition of CH2Cl2 (3 mL), filtrationand evaporation of solvent. Purification by silica gel column chromatography (n-hexane-EtOAc 0.6percent)afforded the title compound as a white crystalline solid in 50percent yield.
References: [1] Molecules, 2013, vol. 18, # 10, p. 11683 - 11704.
[2] Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation), 1983, vol. 32, # 2, p. 265 - 270[3] Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, 1983, # 2, p. 299 - 304.
 

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