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[ CAS No. 301359-45-5 ]

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2D
Chemical Structure| 301359-45-5
Chemical Structure| 301359-45-5
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Product Details of [ 301359-45-5 ]

CAS No. :301359-45-5MDL No. :MFCD00492553
Formula : C14H15ClN2O2S Boiling Point : 403.2±55.0°C at 760 mmHg
Linear Structure Formula :-InChI Key :-
M.W :310.80Pubchem ID :3145501
Synonyms :

Computed Properties of [ 301359-45-5 ]

TPSA : 82.4 H-Bond Acceptor Count : 3
XLogP3 : 2.6 H-Bond Donor Count : 2
SP3 : 0.29 Rotatable Bond Count : 4

Safety of [ 301359-45-5 ]

Signal Word:WarningClass:N/A
Precautionary Statements:P261-P305+P351+P338UN#:N/A
Hazard Statements:H302-H315-H319-H335Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 301359-45-5 ]

  • Upstream synthesis route of [ 301359-45-5 ]
  • Downstream synthetic route of [ 301359-45-5 ]

[ 301359-45-5 ] Synthesis Path-Upstream   1~3

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  • [ 17356-08-0 ]
  • [ 301359-45-5 ]
YieldReaction ConditionsOperation in experiment
86% With nanometasilica disulfuric acid In neat (no solvent) at 80℃; for 0.25 h; Green chemistry General procedure: Nanometasilica disulfuric acid (NMSDSA) (10 mol percent;0.024 g) or nanometasilica monosulfuric acid sodium salt(NMSMSA) (10 mol percent; 0.018 g) as a green mild catalystwas added to a mixture of aromatic aldehydes (1 mmol), ethylacetoacetate (1 mmol; 0.132 g) and urea (1.5 mmol; 0.090)or thiourea (1.5 mmol; 0.114) in a round-bottomed flask, andthe subsequent mixture was firstly stirred magnetically undersolvent-free conditions at 80 °C. After completion of the reaction,as checked by TLC n-hexane/ethyl acetate (5:2), ethylacetate (10 mL) was added to a reaction mixture, stirred andrefluxed for 5 min, and then was washed with water (10 mL)and decanted to separate catalyst from the reaction mixture(the reaction mixture was soluble in hot ethyl acetate andNMSDSA or NMSMSA catalyst was soluble in water). Thesolvent of organic layer was evaporated, and the crude productwas purified via recrystallization from ethanol/water (10:1).
85% at 100℃; for 0.5 h; Green chemistry General procedure: A mixture of aldehyde 1 (2 mmol), 1,3-dicarbonyl compounds (ethyl acetoacetate or acetylacetone, 2 mmol), urea or thiourea (2.4 mmol), and β-CD-PSA (0.02 mmol) was stirred at 100 °C for the appropriate time (monitored by TLC). Then, water (5 mL) was added and the reaction mixture filtered. The solution of β-CD-PSA was dried under vacuum for recycling catalyst in next run. Pure 3,4-dihydropyrimidinones were afforded by evaporation of the solvent followed by recrystallization from ethanol. All were characterized by spectral data and comparison of their physical data with the literature.
85% With Punica granatum peel In neat (no solvent) at 100℃; for 0.25 h; Green chemistry General procedure: To a mixture of benzaldehyde (1 mmol, 0.106 g), ethyl acetoacetate (1 mmol,0.130 g) and Punica granatum peel (0.03 g) at 100 °C, urea (1 mmol, 0.060 g) was added with stirring. The progress of the reaction was monitored by thin layer chromatography (TLC). After completion of the reaction, the reaction mixture was cooled to room temperature. Then, cold distilled water (5 mL) was poured into the reaction flask, and the resultant mixture was decanted. The brown precipitate was dissolved in hot EtOH (3 mL) and the catalyst was separated by filtration. Then, the filtrate was distilled under reduced pressure and finally the crude product was recrystallized by EtOH to give the pure product (0.247 g, 95percent).
84% With bis(p-sulfoanilino)triazine-functionalized silica-coated magnetite nanoparticles In neat (no solvent) at 100℃; for 1.25 h; General procedure: A mixture of aromatic aldehyde (1 mmol), b-keto ester or dimedone (1 mmol) and urea or thiourea (1.2 mmol) was stirred in presence MNPs-BSAT (20 mg) at 100 °C under solvent-free condition for the appropriate time (Scheme 1). After completion of the reaction as indicated by TLC (using n-hexane-ethyl acetate as eluent), the resulting mixture was diluted with hot ethanol (15 mL) and the catalyst separated by an external magnet and washed with hot ethanol (5 mL) two times. The filtrate was cooled to room temperature and the crude products which precipitated were collected and recrystallized from ethanol if necessary.
81% With cellulose sulfuric acid In water at 100℃; for 5 h; General procedure: General procedure for the synthesis of DHPMs (4a-4m)
A mixture of aromatic aldehyde (0.01 moles), ethyl acetoacetate (0.012 moles) and urea (0.01 moles) was stirred in water at 100 °C utilizing CSA (0.05 g) for 3.5-6.5 h, the reaction was monitored by thin layer chromatography (TLC) [6:4 hexane:ethyl acetate].
After the completion of reaction, the reaction mixture was cooled and washed with ice cooled water and the solid precipitate was separated by filtration and dried in vacuum, which was passed over a column of silica gel (60-100 mesh) and then recrystallized from methanol.
81% With phenylacetic acid coated Fe3O4, sulfonated In neat (no solvent) at 20℃; for 2.58333 h; General procedure: In a typical procedure, a mixture of aldehyde (1 mmol), ethylacetoacetate (1 mmol), urea (or thiourea) (1.2 mmol) and Fe3O4/PAA-SO3H (0.06 g) was placed in a round-bottom flask. The suspension was stirred at room temperature. Completion of the reaction was monitored by Thin Layer Chromatography (TLC). After completion of the reaction, the catalyst was separated from the solid crude product using an external magnet. The precipitated solid was then collected and recrystallized from ethanol to afford the pure product.The product was identified with 1H NMR, 13C NMR and FT-IR spectroscopy techniques.
72% With sulfuric acid In ethanol at 80℃; for 3 h; General procedure: Ethyl acetoacetate (2.6mmol), different aromatic aldehydes (2.5mmol), urea (2.6mmol), few drops of sulfuric acid and 13ml ethanol were mixed together. The reaction mixure was refluxed at 80°C for 3h, then cooled to room temperature and poured into crushed ice. The precipitate was filtered & finally washed with cold water. The derivatives were recrystallized with acetonitrile to get K10–17 compounds.
66% at 90℃; for 12 h; Green chemistry General procedure: In a 25 mL roundbottom flask located with aldehyde (0.3 mmol), ethyl acetoacetate (0.3 mmol), and thiourea(0.45 mmol) was added EL (2 mL) and TMSCl (0.45 mmol). The mixture was heated at 90 C for 12 h (TLC). After being cooled down to room temperature, water (10 mL) wasadded and the resulting mixture was extracted with (3 × 10 mL) ethyl acetate. The organicphases were combined and dried over anhydrous Na2SO4. The solid was filtered out andthe solution was subjected to vacuum evaporation to remove solvent. Finally, the residuewas subjected to silica column chromatography (V3:1 of petroleum ether and ethyl acetateas eluent) to give the pure product.
40% With 1-sulfonic acid-3,5,7-trimethylpurinium-5,7-dione hydrogen sulfate In neat (no solvent) at 50℃; for 5 h; Ionic liquid; Green chemistry General procedure: A mixture of an aromatic aldehyde (1.0 mmol), ethylacetoacetate (1.0 mmol, 0.13 mL) or acetylacetone (1.0mmol, 0.1 mL), urea(1.2 mmol, 0.072 g), or thiourea (1.2mmol, 0.086 g), and [Simp]HSO4 (0.01 mmol, 0.004 g) washeated at 50 °C for an appropriate time (Table 3). Aftercompletion of the reaction, the residue was washed withwater for several times. The filtrate was recrystallized fromethanol to afford the pure product.

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[4] Synthetic Communications, 2009, vol. 39, # 5, p. 880 - 886
[5] Tetrahedron Letters, 2009, vol. 50, # 24, p. 2889 - 2892
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[11] Journal of the Iranian Chemical Society, 2017, vol. 14, # 1, p. 121 - 134
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[15] Journal of Molecular Catalysis A: Chemical, 2013, vol. 370, p. 197 - 204
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[17] New Journal of Chemistry, 2017, vol. 41, # 14, p. 6893 - 6901
[18] Bulletin of the Korean Chemical Society, 2010, vol. 31, # 6, p. 1715 - 1718
[19] Synthesis and Reactivity in Inorganic, Metal-Organic and Nano-Metal Chemistry, 2011, vol. 41, # 9, p. 1135 - 1140
[20] Applied Organometallic Chemistry, 2017, vol. 31, # 4,
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[23] Bioorganic Chemistry, 2016, vol. 68, p. 265 - 274
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[25] Phosphorus, Sulfur and Silicon and the Related Elements, 2014, vol. 189, # 6, p. 791 - 795
[26] Tetrahedron Letters, 2007, vol. 48, # 33, p. 5777 - 5780
[27] Croatica Chemica Acta, 2017, vol. 90, # 1,
[28] Catalysis Science and Technology, 2014, vol. 4, # 1, p. 71 - 80
[29] Indian Journal of Heterocyclic Chemistry, 2010, vol. 19, # 3, p. 273 - 276
[30] Tetrahedron Letters, 2013, vol. 54, # 14, p. 1862 - 1865
[31] Chemical Communications, 2014, vol. 50, # 88, p. 13555 - 13558
[32] Chinese Chemical Letters, 2017, vol. 28, # 5, p. 1074 - 1078
[33] European Journal of Medicinal Chemistry, 2017, vol. 138, p. 140 - 151
[34] Letters in Organic Chemistry, 2018, vol. 15, # 4, p. 241 - 245
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  • [ 89-98-5 ]
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YieldReaction ConditionsOperation in experiment
90% at 110℃; for 1 h; General procedure: A mixture of aldehyde (4 mmol), β-ketoester (4 mmol), and ammonium thiocyanate (4.8 mmol) was heated at 110 °C. The reaction was monitored by thin layer chromatography. After completion of the reaction, the mixture was cooled to room temperature and quenched with water (5 mL); solid precipitated was filtered at vacuum pump, washed with water (3 X 5 mL), dried under vacuum and recrystallized from methanol and acetone (8:2) to afford the pure products
Reference: [1] Tetrahedron Letters, 2017, vol. 58, # 18, p. 1778 - 1780
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Reference: [1] Letters in Organic Chemistry, 2018, vol. 15, # 4, p. 241 - 245
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