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CAS No. :16619-60-6 MDL No. :MFCD01047294
Formula : C15H14N2 Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W : 222.29 Pubchem ID :-
Synonyms :

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Application In Synthesis of [ 16619-60-6 ]

* 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.

  • Downstream synthetic route of [ 16619-60-6 ]

[ 16619-60-6 ] Synthesis Path-Downstream   1~4

  • 1
  • [ 16619-60-6 ]
  • [ 1145-01-3 ]
YieldReaction ConditionsOperation in experiment
79.3% palladium; In water; 1,2-dichloro-ethane; EXAMPLE 17 3,5-Diphenyl-2-pyrazoline (21.9 parts) is dissolved in ethylene dichloride (75 parts by volume). There is next added 5% palladium on carbon catalyst (4 parts containing 40% water) is added and the mixture is heated at reflux for 8 hours. There is obtained 3,5-diphenylpyrazole in a 79.3% yield whose melting point ranges from 196C. to 200C.
79.3% palladium; In water; 1,2-dichloro-ethane; EXAMPLE 17 3,5-Diphenyl-2-pyrazoline (21.9 parts) is dissolved in ethylene dichloride (75 parts by volume). There is next added 5% palladium on carbon catalyst (4 parts containing 40% water) is added and the mixture is heated at reflux for 8 hours. There is obtained 3,5-diphenylpyrazole in a 79.3% yield whose melting point ranges from 196 to 200 C.
With sulfuric acid; In neat (no solvent); at 20℃; for 3h;Green chemistry; General procedure: A mixture of chalcones (2 mmol), hydrazine derivatives (2 mmol) and nano TiO2 (20%) was heated at 60 C. The progress of the reaction was monitored by TLC. After the completion of the reaction, the mixture was added TCM(2 mmol) and sulphuric acid (0.2 mL). The reaction mixture was stirred vigorously at room temperature for 3 h. The mixture was washed with chloroform and filtered to recover the catalyst. The filtrate was evaporated and the crude product was recrystallized from iso-propanol to afford the pure pyrazoles derivatives. 31
  • 2
  • [ 94-41-7 ]
  • [ 16619-60-6 ]
YieldReaction ConditionsOperation in experiment
87% With titanium(IV) oxide; hydrazine In neat (no solvent) at 60℃; Green chemistry; General procedure for the synthesis of pyrazole via condensation of chalcones and hydrazine General procedure: A mixture of chalcones (2 mmol), hydrazine derivatives (2 mmol) and nano TiO2 (20%) was heated at 60 °C. The progress of the reaction was monitored by TLC. After the completion of the reaction, the mixture was added TCM(2 mmol) and sulphuric acid (0.2 mL). The reaction mixture was stirred vigorously at room temperature for 3 h. The mixture was washed with chloroform and filtered to recover the catalyst. The filtrate was evaporated and the crude product was recrystallized from iso-propanol to afford the pure pyrazoles derivatives. 31
85% With thionyl chloride; hydrazine hydrate In diethyl ether at 60℃; for 0.5h; Synthesis of pyrazolines derivatives: [1H-3-(substituted aryl)-5-(substituted phenyl)-2-pyrazolines] General procedure: An appropriate equi-molar quantities of substituted styryl aryl ketones (2 mmol), hydrazine hydrate (2 mmol) and SOCl2 (0.5 mL) was warmed (60 °C) in (15 mL) of diethylether for 30 min (Scheme 1) in water bath. The progress of the reaction was monitored by TLC. The reaction mixture was cooled, and poured into cold water. The precipitate was filtered, dried and subjected to column chromatography using hexane and ethyl acetate (3:1) as eluent. The yield, analytical and mass spectral data are presented in Table 1. The IR and NMR spectral data are given in Table 2.
83% Stage #1: benzalacetophenone With hydrazine hydrate at 20 - 25℃; for 0.666667h; Sealed tube; Milling; Green chemistry; Stage #2: With copper diacetate for 1h; Sealed tube; Milling; Green chemistry;
76.8% With hydrazine hydrate In ethanol for 6h; Reflux; General procedure for the synthesis of 3,5-diphenylpyrazolines General procedure: A mixture of chalcone (0.01 mol) and hydrazine hydrate (0.02 mol) was heated at reflux for 6 h in absolute ethanol(50 ml). The solution was left to cool at room temperature and the solid formed was filtered off, washed with water, dried and crystallized from absolute ethanol. Spectral analysis of the synthesized hydrazones is consistent with the proposed structures and with those reported.42
With ethanol; hydrazine hydrate
With hydrazine hydrate for 1h; Heating;
With hydrazine hydrate for 0.25h; Heating;
With hydrazine hydrate In ethanol for 2h; Heating;
With hydrazine hydrate In ethanol for 4h; Heating;
With sodium hydroxide; hydrazine hydrate In ethanol for 4h; Reflux;
With hydrazine hydrate In ethanol Reflux;
With hydrazine hydrate at 20 - 25℃; for 0.666667h; Sealed tube; Milling; Green chemistry;
With hydrazine hydrate In ethanol; isopropyl alcohol; acetone at 80℃; for 5h; 1 Synthesis of [1,4] dioxin-6-yl) (3,5-diphenyl-4,5-dihydro-1H-pyrazol- 1 - yl) methanone (compound 1a) 5.0mmol of acetophenone and 5lmmol benzaldehyde into the 50ml round bottom burning, adding 20ml of anhydrous ethanol, magnetic stirring lOmin to mix evenly, slowly dropping 40% NaOH solution 10ml, magnetic stirring, room temperature reaction 2h TLC). The product was precipitated as a solid, filtered and washed with a large amount of distilled water. The solid was washed three times with cold ethanol (3 ml each) and dried. The product was mixed with ethanol and acetone (volume ratio: Acetone = 10: 1). The compound obtained above was added to a 50 ml flask and heated to 80 ° C in 20 ml of isopropanol (or 20 ml of ethanol). To the solution was added dropwise 2 mmol of hydrazine hydrate 80, The reaction was stirred at 80 ° C for 5 h (TLC). After the end of the reaction, the distillation was carried out under reduced pressure until all of the ethanol was distilled off. The product was precipitated in a large amount as a solid, filtered and washed three times with cold ethanol (each about 3 ml). Within 20 min, 1.0 mmol of the obtained product, 1,4-benzodioxan-6-carboxylic acid was dissolved in 20 ml of methylene chloride at room temperature. 1.5 mmol of EDCI and 0.05 mmol of HOBt were added and the reaction was stirred for 10 h (TLC). After the completion of the reaction, the reaction solution was washed three times with 50 ml of water (150 ml each), and the resulting aqueous phase was combined three times, and extracted twice with 210 ml of ethyl acetate (70 ml each). The organic phase (dichloromethane and ethyl acetate) And distilled to dryness under reduced pressure to give a solid product which was recrystallized from a mixture of ethanol and acetone (volume ratio of ethanol: acetone = 10: 1) to give the title compound (white crystals).
With hydrazine hydrate In isopropyl alcohol for 4h; Reflux; 4.2.2. Synthesis of 3,5-diphenyl-4,5-dihydro-1H-pyrazole (D01-D16) General procedure: A mixture of C (1.0 mmol) and hydrazine hydrate (2.0 mmol)was dissolved in i-PrOH (5 mL) and refluxed for 4 h. The reactionmixture was cooled and kept at -20 °C overnight. Then the solidobtained was filtered off and washed with petroleum ether andtaken for the next step immediately. Following this method, we gotcrude compounds D01-D16.
With hydrazine hydrate In chloroform at 80℃; for 12h;

Reference: [1]Akbari, Ali; Mirjalili, Bibi Fatemeh [Revue Roumaine de Chimie, 2016, vol. 61, # 2, p. 119 - 123]
[2]Ranganathan, Kaliyaperumal; Suresh, Ramamoorthy; Vanangamudi, Ganesan; Thirumurthy, Kannan; Mayavel, Perumal; Thirunarayanan, Ganesamoorthy [Bulletin of the Chemical Society of Ethiopia, 2014, vol. 28, # 2, p. 271 - 288]
[3]Zhang, Ze; Tan, Ya-Jun; Wang, Chun-Shan; Wu, Hao-Hao [Heterocycles, 2014, vol. 89, # 1, p. 103 - 112]
[4]Raghav, Neera; Singh, Mamta [Bioorganic and Medicinal Chemistry, 2014, vol. 22, # 15, p. 4233 - 4245]
[5]Kishner [Zhurnal Russkago Fiziko-Khimicheskago Obshchestva, 1915, vol. 47, p. 1102][Chemisches Zentralblatt, 1916, vol. 87, # I, p. 1063]
[6]Applequist, Douglas E.; Gdanski, Rick D. [Journal of Organic Chemistry, 1981, vol. 46, # 12, p. 2502 - 2510]
[7]El-Rayyes, Nizar R.; Hovakeemian, George H.; Hmoud, Hayat S. [Journal of Chemical and Engineering Data, 1984, vol. 29, # 2, p. 225 - 229]
[8]Bilgin; Palaska; Sunal [Arzneimittel-Forschung/Drug Research, 1993, vol. 43, # 10, p. 1041 - 1044] Malhotra, Vineet; Pathak, Seema; Nath, Rajendra; Mukerjee, Devashis; Shanker, Kirpa [Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2002, vol. 41, # 6, p. 1310 - 1313]
[9]Turan-Zitouni, Guelhan; Oezdemir, Ahmet; Kaplancikli, Zafer Asim; Chevallet, Pierre; Tunali, Yagmur [Phosphorus, Sulfur and Silicon and the Related Elements, 2005, vol. 180, # 12, p. 2717 - 2724]
[10]Location in patent: experimental part Siddiqui, Nadeem; Alam, Perwaiz; Ahsan, Waquar [Archiv der Pharmazie, 2009, vol. 342, # 3, p. 173 - 181]
[11]Location in patent: experimental part Kaplancikli, Zafer Asim; Turan-Zitouni, Guelhan; Oezdemir, Ahmet; Devrim Can, Oezguer; Chevallet, Pierre [European Journal of Medicinal Chemistry, 2009, vol. 44, # 6, p. 2606 - 2610]
[12]Zhang, Ze; Tan, Ya-Jun; Wang, Chun-Shan; Wu, Hao-Hao [Heterocycles, 2014, vol. 89, # 1, p. 103 - 112]
[13]Current Patent Assignee: NANJING UNIVERSITY - CN103304546, 2016, B Location in patent: Paragraph 0033-0035
[14]Zhang, Ya-Liang; Li, Bo-Yan; Yang, Rong; Xia, Lin-Ying; Fan, A-Li; Chu, Yi-Chun; Wang, Lin-Jian; Wang, Zhong-Chang; Jiang, Ai-Qin; Zhu, Hai-Liang [European Journal of Medicinal Chemistry, 2019, vol. 163, p. 896 - 910]
[15]Anisimova, Natalia Y.; Choe, Jun-yong; Lavecchia, Antonio; Loiodice, Fulvio; Meyer-Almes, Franz-Josef; Pokrovsky, Vadim S.; S Ramaa, C.; Smirnova, Galina B.; Sokolova, Darina V.; Spirina, Tatiana S.; Tilekar, Kalpana; Upadhyay, Neha [ChemMedChem, 2020, vol. 15, # 19, p. 1813 - 1825]
  • 3
  • [ 16619-60-6 ]
  • [ 4442-54-0 ]
  • [ 1403750-19-5 ]
YieldReaction ConditionsOperation in experiment
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 20℃; for 10h; General procedure: Method I Ba (1 mmol) and <strong>[4442-54-0]2,3-dihydrobenzo[b][1,4]dioxin-6-carboxylic acid</strong> (or 2,3-dihydrobenzo[b][1,4]dioxin-2-carboxylic acid) (1 mmol) together with EDCI (1.5 mmol) and HOBt (0.05 mmol) in CH2Cl2 (20 mL) were refluxed at room temperature for 10 h. While the reaction completed, the solution was washed with water for three times (30 mL each time). The remaining water layer was extracted by EtOAc for three times (30 mL each time). The organic layers (CH2Cl2 and EtOAc) were combined and then evaporated. The separated solid was crystallized from mixture of DMF and ethanol (9:1) to obtain the corresponding compound as translucent solid. White crystal, mp: 120-121 °C. 1H NMR (CDCl3, 300 MHz) delta: 3.15-3.23 (d, J = 17.7 Hz, 1H), 3.69-3.79 (m, 1H), 4.31-4.32 (t, J = 2.4 Hz, 4H), 5.79-5.85 (m, 1H), 6.90-6.93 (d, J = 8.4 Hz, 1H), 7.27-7.37 (m, 5H), 7.43-7.44 (m, 3H), 7.65-7.68 (d, J = 8.1 Hz, 2H), 7.73-7.75 (m, 2H). MS (ESI): 385.15 (C24H21N2O3, [M+H]+). Anal. Calcd for C24H20N2O3: C, 74.98; H, 5.24; N, 7.29; O, 12.49. Found: C, 74.59; H, 5.23; N, 7.30.
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 20℃; for 10h; 5.0mmol of acetophenone and 5lmmol benzaldehyde into the 50ml round bottom burning, adding 20ml of anhydrous ethanol, magnetic stirring lOmin to mix evenly, slowly dropping 40percent NaOH solution 10ml, magnetic stirring, room temperature reaction 2h TLC). The product was precipitated as a solid, filtered and washed with a large amount of distilled water. The solid was washed three times with cold ethanol (3 ml each) and dried. The product was mixed with ethanol and acetone (volume ratio: Acetone = 10: 1). The compound obtained above was added to a 50 ml flask and heated to 80 ° C in 20 ml of isopropanol (or 20 ml of ethanol). To the solution was added dropwise 2 mmol of hydrazine hydrate 80, The reaction was stirred at 80 ° C for 5 h (TLC). After the end of the reaction, the distillation was carried out under reduced pressure until all of the ethanol was distilled off. The product was precipitated in a large amount as a solid, filtered and washed three times with cold ethanol (each about 3 ml). Within 20 min, 1.0 mmol of the obtained product, 1,4-benzodioxan-6-carboxylic acid was dissolved in 20 ml of methylene chloride at room temperature. 1.5 mmol of EDCI and 0.05 mmol of HOBt were added and the reaction was stirred for 10 h (TLC). After the completion of the reaction, the reaction solution was washed three times with 50 ml of water (150 ml each), and the resulting aqueous phase was combined three times, and extracted twice with 210 ml of ethyl acetate (70 ml each). The organic phase (dichloromethane and ethyl acetate) And distilled to dryness under reduced pressure to give a solid product which was recrystallized from a mixture of ethanol and acetone (volume ratio of ethanol: acetone = 10: 1) to give the title compound (white crystals).
  • 4
  • [ 16619-60-6 ]
  • [ 3663-80-7 ]
  • [ 1403750-40-2 ]
YieldReaction ConditionsOperation in experiment
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 20℃; for 10h; Method I Ba (1 mmol) and 2,3-dihydrobenzo[b][1,4]dioxin-6-carboxylic acid (or <strong>[3663-80-7]2,3-dihydrobenzo[b][1,4]dioxin-2-carboxylic acid</strong>) (1 mmol) together with EDCI (1.5 mmol) and HOBt (0.05 mmol) in CH2Cl2 (20 mL) were refluxed at room temperature for 10 h. While the reaction completed, the solution was washed with water for three times (30 mL each time). The remaining water layer was extracted by EtOAc for three times (30 mL each time). The organic layers (CH2Cl2 and EtOAc) were combined and then evaporated. The separated solid was crystallized from mixture of DMF and ethanol (9:1) to obtain the corresponding compound as translucent solid. 4.5.16 (2,3-Dihydrobenzo[b][1,4]dioxin-2-yl)(3,5-diphenyl-4,5-dihydro-1H-pyrazol-1-yl)methanone (D1) White crystal, mp: 201 °C. 1H NMR (CDCl3, 300 MHz) delta: 3.21-3.27 (m, 1H), 3.79-3.83 (m, 1H), 4.38-4.46 (m, 1H), 4.53-4.63 (m, 1H), 5.59-5.66 (m, 2H), 6.82-6.88 (m, 3H), 6.99-7.00 (d, J = 4.8 Hz, 1H), 7.21-7.26 (m, 3H), 7.30-7.34 (m, 2H), 7.44-7.48 (m, 3H), 7.75-7.76 (d, J = 3.9 Hz, 2H). MS (ESI): 385.15 (C24H21N2O3, [M+H]+). Anal. Calcd for C24H20N2O3: C, 74.98; H, 5.24; N, 7.29; O, 12.49. Found: C, 74.61; H, 5.23; N, 7.31.
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