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[ CAS No. 128958-65-6 ] {[proInfo.proName]}

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Chemical Structure| 128958-65-6
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Product Details of [ 128958-65-6 ]

CAS No. :128958-65-6 MDL No. :MFCD00564772
Formula : C14H14N2O2 Boiling Point : -
Linear Structure Formula :- InChI Key :LZMCSSDFZRJZIS-UHFFFAOYSA-N
M.W : 242.27 Pubchem ID :1526486
Synonyms :

Calculated chemistry of [ 128958-65-6 ]

Physicochemical Properties

Num. heavy atoms : 18
Num. arom. heavy atoms : 12
Fraction Csp3 : 0.07
Num. rotatable bonds : 5
Num. H-bond acceptors : 3.0
Num. H-bond donors : 2.0
Molar Refractivity : 68.32
TPSA : 64.35 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.54 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.04
Log Po/w (XLOGP3) : 1.74
Log Po/w (WLOGP) : 1.72
Log Po/w (MLOGP) : 2.36
Log Po/w (SILICOS-IT) : 1.76
Consensus Log Po/w : 1.92

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 0.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -2.6
Solubility : 0.606 mg/ml ; 0.0025 mol/l
Class : Soluble
Log S (Ali) : -2.71
Solubility : 0.474 mg/ml ; 0.00196 mol/l
Class : Soluble
Log S (SILICOS-IT) : -4.71
Solubility : 0.00476 mg/ml ; 0.0000196 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 2.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.7

Safety of [ 128958-65-6 ]

Signal Word:Warning Class:
Precautionary Statements:P233-P260-P261-P264-P271-P280-P302+P352-P304-P304+P340-P305+P351+P338-P312-P321-P332+P313-P337+P313-P340-P362-P403-P403+P233-P405-P501 UN#:
Hazard Statements:H315-H319-H335 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 128958-65-6 ]

* 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 [ 128958-65-6 ]

[ 128958-65-6 ] Synthesis Path-Downstream   1~84

  • 1
  • [ 75-44-5 ]
  • [ 128958-65-6 ]
  • [ 147807-38-3 ]
YieldReaction ConditionsOperation in experiment
76% In 1,4-dioxane for 0.5h;
  • 2
  • [ 56441-55-5 ]
  • [ 128958-65-6 ]
YieldReaction ConditionsOperation in experiment
74% With hydrazine hydrate In propan-1-ol for 48h; Heating;
With hydrazine hydrate In methanol for 6h; Heating;
With hydrazine hydrate In ethanol for 72h; Reflux;
With hydrazine hydrate
With hydrazine hydrate
With hydrazine hydrate In ethanol for 6h; Reflux; Synthesis of 4-alkoxy Benzoyl Hydrazine (3a-3u) 4-Alkoxy benzoic acid ethyl ester (12.7 mmol) and 20mL of ethanol were dissolved in 100 mL reaction flask andstirred at room temperature. Hydrazine hydrate (1.27 g, 25.4mmol) was added drop-wise to the mixture. The mixture washeated under reflux for 6 h. The solvent was evaporated underreduced pressure after the reaction completed to give the residue, which was washed with 100 mL water to obtain awhite solid (3a-3u).
With hydrazine hydrate In neat (no solvent) at 120℃; Sealed tube;
With hydrazine hydrate In neat (no solvent) at 120℃; Sealed tube; - Route B (R1 = aryl) General procedure: Note: hydrazine and carbon disulphide used during this procedure have to be handled withcaution.The carboxylic compound was first converted into its ethyl ester by refluxing in absoluteethanol in the presence of a few drops of H2SO4. The ester was then treated overnight withhydrazine hydrate (2 to 4 equiv.) without solvent at 120 °C. Evaporation of excess hydrazineyielded the corresponding hydrazide compound. The hydrazide, solubilized in absolute ethanol,was treated with CS2 (5 equiv.) in the presence of KOH (1.7 equiv.) at 85 °C for 3 h. Water wasadded and pH was adjusted to 2-3 with 1N HCl. The formed precipitate was collected byfiltration and washed with water, yielding the 1,3,4-oxadiazol-thione, which was used withoutfurther purification. Finally, the preceding compound was treated with hydrazine hydrate (10equiv.) in absolute ethanol at 100 °C overnight in a sealed tube. After evaporation of excesshydrazine, the residue was purified on a silica gel column to yield the final compound.
With hydrazine hydrate In ethanol at 100℃; Sealed tube; General procedure: The ester was then solubilized in EtOH and treated with hydrazine, hydrate (5 equiv.). The mixture was refluxed overnight and solvents were evaporated. Diethyl ether was added and the formed precipitate was filtered and washed with the same solvent to yield the expected hydrazide compound as a powder.
With hydrazine hydrate In ethanol at 100℃; Sealed tube; - General synthetic procedure for the preparation of hydrazides R1-CO-NHNH2 General procedure: To a solution of the acid R1-CO2H in EtOH was added concentrated H2SO4 (2 equiv.) and thereaction mixture was refluxed for 5h. After cooling to room temperature, water was added andthe solution was neutralized with Na2CO3. The aqueous phase was extracted twice with EtOAc.The organic phases were combined, dried over MgSO4, filtered and evaporated under vacuumto yield the ethyl ester, which was used without necessity of purification. The ester was then solubilized in EtOH and treated with hydrazine, hydrate (5 equiv.). Themixture was refluxed overnight and solvents were evaporated. Diethyl ether was added and the formed precipitate was filtered and washed with the same solvent to yield the expectedhydrazide compound as a powder.

Reference: [1]Mazouz; Gueddari; Burstein; Mansuy; Milcent [Journal of Medicinal Chemistry, 1993, vol. 36, # 9, p. 1157 - 1167]
[2]Li, Yan; Liu, Jie; Zhang, Hongquan; Yang, Xiangping; Liu, Zhaojie [Bioorganic and Medicinal Chemistry Letters, 2006, vol. 16, # 8, p. 2278 - 2282]
[3]Location in patent: scheme or table El Bakali, Jamal; Klupsch, Frederique; Guedin, Aurore; Brassart, Bertrand; Fontaine, Gaelle; Farce, Amaury; Roussel, Pascal; Houssin, Raymond; Bernier, Jean-Luc; Chavatte, Philippe; Mergny, Jean-Louis; Riou, Jean-Francois; Henichart, Jean-Pierre [Bioorganic and Medicinal Chemistry Letters, 2009, vol. 19, # 13, p. 3434 - 3438]
[4]Location in patent: scheme or table Ghani, Usman; Ullah, Nisar [Bioorganic and Medicinal Chemistry, 2010, vol. 18, # 11, p. 4042 - 4048]
[5]Location in patent: scheme or table Hu, Lang-Xi; Li, De-Jiang [Heterocyclic Communications, 2010, vol. 16, # 2-3, p. 73 - 77]
[6]Zhu, Zi-Shi; Wang, Shi-Ben; Deng, Xian-Qing; Liu, Da-Chuan; Quan, Zhe-Shan [Letters in drug design and discovery, 2014, vol. 11, # 5, p. 628 - 635]
[7]Sevaille, Laurent; Gavara, Laurent; Bebrone, Carine; De Luca, Filomena; Nauton, Lionel; Achard, Maud; Mercuri, Paola; Tanfoni, Silvia; Borgianni, Luisa; Guyon, Carole; Lonjon, Pauline; Turan-Zitouni, Gülhan; Dzieciolowski, Julia; Becker, Katja; Bénard, Lionel; Condon, Ciaran; Maillard, Ludovic; Martinez, Jean; Frère, Jean-Marie; Dideberg, Otto; Galleni, Moreno; Docquier, Jean-Denis; Hernandez, Jean-François [ChemMedChem, 2017, vol. 12, # 12, p. 972 - 985]
[8]Baud, Damien; Bebrone, Carine; Becker, Katja; Benvenuti, Manuela; Cerboni, Giulia; Chelini, Giulia; Cutolo, Giuliano; De Luca, Filomena; Docquier, Jean-Denis; Feller, Georges; Fischer, Marina; Galleni, Moreno; Gavara, Laurent; Gresh, Nohad; Kwapien, Karolina; Legru, Alice; Mangani, Stefano; Mercuri, Paola; Pozzi, Cecilia; Sannio, Filomena; Sevaille, Laurent; Tanfoni, Silvia; Verdirosa, Federica; Berthomieu, Dorothée; Bestgen, Benoît; Frère, Jean-Marie; Hernandez, Jean-François [European Journal of Medicinal Chemistry, 2020, vol. 208]
[9]Gavara, Laurent; Legru, Alice; Verdirosa, Federica; Sevaille, Laurent; Nauton, Lionel; Corsica, Giuseppina; Mercuri, Paola Sandra; Sannio, Filomena; Feller, Georges; Coulon, Rémi; De Luca, Filomena; Cerboni, Giulia; Tanfoni, Silvia; Chelini, Giulia; Galleni, Moreno; Docquier, Jean-Denis; Hernandez, Jean-François [Bioorganic Chemistry, 2021, vol. 113]
[10]Legru, Alice; Verdirosa, Federica; Hernandez, Jean-François; Tassone, Giusy; Sannio, Filomena; Benvenuti, Manuela; Conde, Pierre-Alexis; Bossis, Guillaume; Thomas, Caitlyn A.; Crowder, Michael W.; Dillenberger, Melissa; Becker, Katja; Pozzi, Cecilia; Mangani, Stefano; Docquier, Jean-Denis; Gavara, Laurent [European Journal of Medicinal Chemistry, 2021, vol. 226]
  • 3
  • [ 128958-65-6 ]
  • [ 107-13-1 ]
  • [ 147807-60-1 ]
YieldReaction ConditionsOperation in experiment
88% In propan-1-ol; n-propanol water 6.e 1st step 1st step 1-(4-benzyloxy benzoyl) 2-(2-cyano ethyl) hydrazine (V) To a solution of 100 mmoles of (4-benzyloxy benzoyl) hydrazine in 200 ml of 1-propanol, 100 mmoles of acrylonitrile are added and the mixture is heated for 24 hours at reflux. Then 50 mmoles of acrylonitrile are added and the heating is continued at reflux for 24 hours. After cooling, the product is filtered and crystallized in a water-ethanol mixture and 26 g (yield: 88%) of the expected product were obtained. melting point=136° C. IR (KBr)ν cm-1: 3290, 3220, 2240, 1670. NMR (DMSO d6) δ ppm: 3 (t, 2H); 4 (t, 2H); 5.2 (s, 2H); 7-8 (m, 9H).
69% In ethanol for 72h; Heating;
68% In ethanol for 48h; Heating;
66% In ethanol for 48h; Heating;
66% In ethanol for 48h; Heating;

  • 4
  • [ 128958-65-6 ]
  • <i>N</i>-(2-methoxy-phenyl)-thioacetimidic acid methyl ester [ No CAS ]
  • 5-(4-Benzyloxyphenyl)-4-(2-methoxyphenyl)-3-methyl-1,2,4-triazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
64% In N,N-dimethyl-formamide at 120℃;
  • 5
  • [ 32122-11-5 ]
  • [ 128958-65-6 ]
YieldReaction ConditionsOperation in experiment
97% With hydrazine hydrate In ethanol for 5h; Heating;
96% With hydrazine hydrate In ethanol for 16h; Reflux;
95% With hydrazine hydrate In methanol Reflux; 2 31.5 g (130 mmol) of methyl 4-benzyloxybenzoate, 120 ml of hydrazine hydrate (80%) and 500 ml of methanol were placed in a 1000 ml three-necked flask, and heated under reflux at 70 ° C. After the reaction was completed, the reaction solution was dried to give a white color. Solid, washed white solid 3 times, filtered,Finally, 4-benzyloxybenzoic acid hydrazide 30 g (yield: 95%) was obtained.
87.5% With hydrazine hydrate In methanol Reflux; To a solution of methyl 4-(benzyloxy)benzoate (40.0 g, 0.165 mol) in MeOH (300 mL) was added N2H4.H20 (80%, 300 mL). The resulting solution was refluxed overnight. After cooled to room temperature, the mixture was concentrated. The resulting solid was dissolved in EA (1000 mL), washed with brine (2 x 300 mL),dried over Na2SO4 and concentrated to dryness to afford desired product 4- (benzyloxy)benzohydrazide 5b(35.0 g, 87.5%). LC-MS [M+Hj 243
73% With hydrazine hydrate In ethanol for 28h; Heating;
With hydrazine In methanol for 72h; Heating / reflux; 16 Preparation 16; 4-Benzyloxy-benzoic acid hydrazide; 4-Benzyloxy-benzoic acid methyl ester (30.9g, 127. 5mmol) and hydrazine hydrate (18.6mL, 381mmol) were dissolved in methanol (600mL) and heated under reflux for 72 hours. The solvent was concentrated to low volume under reduced pressure and was then cooled. The precipitate that formed was filtered off, washed with methanol and dried in vacuo to yield the title product. H NMR (DMSO-D6, 400MHz) o : 4.40 (m, 2H), 5.14 (s, 2H), 7.03 (d, 2H), 7.34 (dd, 1H), 7.38 (t, 2H), 7.43 (m, 2H), 7.77 (d, 2H), 9.56 (s, 1H). MS APCI+ m/z 243 [MH] +
With hydrazine hydrate
With hydrazine hydrate In ethanol for 6h; Reflux; 3.3. Synthesis of 4-(Benzyloxy)benzohydrazide (4) For the synthesis of the substituted benzohydrazide, a mixture of the corresponding ester(20 mmol), 85% hydrazine hydrate (20 mmol) in ethanol (35 mL) was refluxed for 6 h. After that,the solution was poured into ice-water. The solid was filtered and recrystallized from ethanol.Colour: white; m.p.138 °C (140 °C reported in chemspider)
With hydrazine hydrate In ethanol for 3h; Sonication; (b) General procedure for the synthesis of 4-(benzyloxy) benzo hydrazide (4): Synthesis of substituted benzo hydrazide was carried out in an ultrasonic processor by taking theequivalent ratio of a mixture of corresponding esters (20 mmol) and 85% hydrazine hydrate (20 mmol)in ethanol for three hours. The completion of reaction was monitored by TLC. The reaction mixturewas poured into ice-water. The solid obtained was filtered, dried, and recrystallized from ethanol.Colour: White, M.P.: 80 °C.
With hydrazine hydrate
With hydrazine hydrate In methanol at 80℃; for 48h;

Reference: [1]Khan, Khalid Mohammad; Rasheed, Maimona; Ullah, Zia; Hayat, Safdar; Kaukab, Farhana; Choudhary, M. Iqbal; Ur-Rahman, Atta; Perveen, Shahnaz [Bioorganic and Medicinal Chemistry, 2003, vol. 11, # 7, p. 1381 - 1387]
[2]Shivakumar, Kilingaru I.; Pociecha, Damian; Szczytko, Jacek; Kapuściński, Szymon; Monobe, Hirosato; Kaszyński, Piotr [Journal of Materials Chemistry C, 2020, vol. 8, # 3, p. 1083 - 1088]
[3]Current Patent Assignee: CHINESE ACADEMY OF MEDICAL SCIENCES - CN108456157, 2018, A Location in patent: Paragraph 0273; 0274; 0276
[4]Current Patent Assignee: ICAHN SCHOOL OF MEDICINE AT MOUNT SINAI - WO2019/18718, 2019, A1 Location in patent: Page/Page column 30; 31
[5]Khan, Khalid Mohammed; Rahat, Shagufta; Choudhary, Muhammad Iqbal; Atta-ur-Rahman; Ghani, Usman; Perveen, Shahnaz; Khatoon, Shagufta; Dar, Ahsana; Malik, Abdul [Helvetica Chimica Acta, 2002, vol. 85, # 2, p. 559 - 570]
[6]Current Patent Assignee: PFIZER INC - WO2005/82866, 2005, A2 Location in patent: Page/Page column 61
[7]Location in patent: scheme or table Rastogi, Nisheeth; Harrison, Darwin Anil; Tripathi, Diwakar; Shukla, Sarveshwar [Journal of the Indian Chemical Society, 2009, vol. 86, # 9, p. 991 - 995]
[8]Nimbalkar, Urja D.; Tupe, Santosh G.; Vazquez, Julio A. Seijas; Khan, Firoz A. Kalam; Sangshetti, Jaiprakash N.; Nikalje, Anna Pratima G. [Molecules, 2016, vol. 21, # 5]
[9]Nimbalkar, Urja D.; Seijas, Julio A.; Borkute, Rachna; Damale, Manoj G.; Sangshetti, Jaiprakash N.; Sarkar, Dhiman; Nikalje, Anna Pratima G. [Molecules, 2018, vol. 23, # 8]
[10]Harrison, Darwin Anil; Rastogi, Nisheeth; Rahman, Masihur [Indian Journal of Heterocyclic Chemistry, 2014, vol. 23, # 4, p. 411 - 418]
[11]Li, Xiaoyang; Jiang, Yuqi; Peterson, Yuri K.; Xu, Tongqiang; Himes, Richard A.; Luo, Xin; Yin, Guilin; Inks, Elizabeth S.; Dolloff, Nathan; Halene, Stephanie; Chan, Sherine S. L.; Chou, C. James [Journal of Medicinal Chemistry, 2020, vol. 63, # 10, p. 5501 - 5525]
  • 6
  • [ 128958-65-6 ]
  • [ 100-39-0 ]
  • N',N'-dibenzyl-4-benzyloxybenzohydrazide [ No CAS ]
YieldReaction ConditionsOperation in experiment
59% In ethanol for 72h; Heating;
  • 7
  • [ 128958-65-6 ]
  • [ 98-88-4 ]
  • N'-benzoyl-4-benzyloxybenzohydrazide [ No CAS ]
YieldReaction ConditionsOperation in experiment
62% In ethanol for 72h; Heating;
  • 8
  • [ 128958-65-6 ]
  • [ 75-03-6 ]
  • 4-benzyloxy-benzoic acid <i>N</i>',<i>N</i>'-diethyl-hydrazide [ No CAS ]
YieldReaction ConditionsOperation in experiment
61% In ethanol for 72h; Heating;
  • 9
  • [ 128958-65-6 ]
  • [ 100-52-7 ]
  • C21H18N2O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
75% In ethanol Heating;
  • 10
  • [ 128958-65-6 ]
  • [ 123-11-5 ]
  • C22H20N2O3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
70% In ethanol Heating;
With acetic acid In ethanol Sonication; (c) General procedure for the synthesis of 4-(benzyloxy)-N0-(substituted benzylidene) benzo hydrazide,called Schiff’s bases 5a-j: General procedure: Schiff’s bases 5a-j were obtained by condensation of equimolar quantities of 4-(benzyloxy) benzohydrazide (0.01 mol) and different substituted aldehydes (0.01 mol) in the presence of glacial aceticacid (0.02 mol) as a catalyst in absolute ethanol kept in an ultra-sonicator for 1 to 2 h. The completion ofthe reaction was monitored by TLC. The reaction mixture was concentrated and cooled. The obtainedsolid was filtered and dried. The product was recrystallized from ethanol.
  • 11
  • [ 128958-65-6 ]
  • [ 104-88-1 ]
  • C21H17ClN2O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
65% In ethanol Heating;
With acetic acid In ethanol Sonication; (c) General procedure for the synthesis of 4-(benzyloxy)-N0-(substituted benzylidene) benzo hydrazide,called Schiff’s bases 5a-j: General procedure: Schiff’s bases 5a-j were obtained by condensation of equimolar quantities of 4-(benzyloxy) benzohydrazide (0.01 mol) and different substituted aldehydes (0.01 mol) in the presence of glacial aceticacid (0.02 mol) as a catalyst in absolute ethanol kept in an ultra-sonicator for 1 to 2 h. The completion ofthe reaction was monitored by TLC. The reaction mixture was concentrated and cooled. The obtainedsolid was filtered and dried. The product was recrystallized from ethanol.
  • 12
  • [ 100-39-0 ]
  • [ 128958-65-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 91 percent / K2CO3 / acetone / 2 h / Heating 2: 97 percent / hydrazine hydrate / ethanol / 5 h / Heating
Multi-step reaction with 2 steps 1: 62 percent / K2CO3 / acetone / 3 h / 60 °C 2: 73 percent / 99 percent hydrazine hydrate / ethanol / 28 h / Heating
  • 13
  • [ 99-76-3 ]
  • [ 128958-65-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 91 percent / K2CO3 / acetone / 2 h / Heating 2: 97 percent / hydrazine hydrate / ethanol / 5 h / Heating
Multi-step reaction with 2 steps 1: 62 percent / K2CO3 / acetone / 3 h / 60 °C 2: 73 percent / 99 percent hydrazine hydrate / ethanol / 28 h / Heating
Multi-step reaction with 2 steps 1: potassium carbonate / N,N-dimethyl-formamide / 4 h / 20 °C / Sonication 2: hydrazine hydrate / ethanol / 6 h / Reflux
Multi-step reaction with 2 steps 1: potassium carbonate / N,N-dimethyl-formamide / 4 h / Sonication 2: hydrazine hydrate / ethanol / 3 h / Sonication
Multi-step reaction with 2 steps 1: potassium iodide; potassium carbonate / acetonitrile / 60 °C 2: hydrazine hydrate / methanol / Reflux
Multi-step reaction with 2 steps 1: potassium carbonate 2: hydrazine hydrate
Multi-step reaction with 2 steps 1: potassium carbonate / acetone / 5 h / Reflux 2: hydrazine hydrate / methanol / Reflux
Multi-step reaction with 2 steps 1: potassium carbonate / acetone / 10 h / Reflux 2: hydrazine hydrate / ethanol / 16 h / Reflux
Multi-step reaction with 2 steps 1: triphenylphosphine; diethylazodicarboxylate / tetrahydrofuran / 2 h / 0 - 20 °C 2: hydrazine hydrate / methanol / 48 h / 80 °C

Reference: [1]Khan, Khalid Mohammad; Rasheed, Maimona; Ullah, Zia; Hayat, Safdar; Kaukab, Farhana; Choudhary, M. Iqbal; Ur-Rahman, Atta; Perveen, Shahnaz [Bioorganic and Medicinal Chemistry, 2003, vol. 11, # 7, p. 1381 - 1387]
[2]Khan, Khalid Mohammed; Rahat, Shagufta; Choudhary, Muhammad Iqbal; Atta-ur-Rahman; Ghani, Usman; Perveen, Shahnaz; Khatoon, Shagufta; Dar, Ahsana; Malik, Abdul [Helvetica Chimica Acta, 2002, vol. 85, # 2, p. 559 - 570]
[3]Nimbalkar, Urja D.; Tupe, Santosh G.; Vazquez, Julio A. Seijas; Khan, Firoz A. Kalam; Sangshetti, Jaiprakash N.; Nikalje, Anna Pratima G. [Molecules, 2016, vol. 21, # 5]
[4]Nimbalkar, Urja D.; Seijas, Julio A.; Borkute, Rachna; Damale, Manoj G.; Sangshetti, Jaiprakash N.; Sarkar, Dhiman; Nikalje, Anna Pratima G. [Molecules, 2018, vol. 23, # 8]
[5]Current Patent Assignee: CHINESE ACADEMY OF MEDICAL SCIENCES - CN108456157, 2018, A
[6]Harrison, Darwin Anil; Rastogi, Nisheeth; Rahman, Masihur [Indian Journal of Heterocyclic Chemistry, 2014, vol. 23, # 4, p. 411 - 418]
[7]Current Patent Assignee: ICAHN SCHOOL OF MEDICINE AT MOUNT SINAI - WO2019/18718, 2019, A1
[8]Shivakumar, Kilingaru I.; Pociecha, Damian; Szczytko, Jacek; Kapuściński, Szymon; Monobe, Hirosato; Kaszyński, Piotr [Journal of Materials Chemistry C, 2020, vol. 8, # 3, p. 1083 - 1088]
[9]Li, Xiaoyang; Jiang, Yuqi; Peterson, Yuri K.; Xu, Tongqiang; Himes, Richard A.; Luo, Xin; Yin, Guilin; Inks, Elizabeth S.; Dolloff, Nathan; Halene, Stephanie; Chan, Sherine S. L.; Chou, C. James [Journal of Medicinal Chemistry, 2020, vol. 63, # 10, p. 5501 - 5525]
  • 14
  • [ 128958-65-6 ]
  • [ 147807-45-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: 66 percent / ethanol / 48 h / Heating 2.1: CHCl3 / 3 h / Heating 2.2: 76 percent / K2CO3 / ethanol / Heating
Multi-step reaction with 2 steps 1: 68 percent / ethanol / 48 h / Heating 2: 64 percent / CHCl3 / 0.5 h / Heating
  • 15
  • [ 120-47-8 ]
  • [ 128958-65-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 1.) NaH / 1.) DMF, RT, 30 min, 2.) DMF, 5 h 2: 74 percent / hydrazine hydrate / propan-1-ol / 48 h / Heating
  • 16
  • [ 128958-65-6 ]
  • 5-(4-Benzyloxy-phenyl)-3-(2-hydroxy-ethyl)-3H-[1,3,4]oxadiazol-2-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 76 percent / dioxane / 0.5 h 2: 1.) NaOH / 1.) EtOH, DMF, RT, 16 h, 2.) EtOH, DMF, 60 deg C, 24 h
  • 17
  • [ 128958-65-6 ]
  • [5-(4-Benzyloxy-phenyl)-2-oxo-[1,3,4]oxadiazol-3-yl]-acetonitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 76 percent / dioxane / 0.5 h 2: 1.) NaOH / 1.) EtOH, DMF, RT, 16 h, 2.) EtOH, DMF, 60 deg C, 24 h
  • 18
  • [ 128958-65-6 ]
  • 2-[5-(4-Benzyloxy-phenyl)-2-oxo-[1,3,4]oxadiazol-3-yl]-propionitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 76 percent / dioxane / 0.5 h 2: 1.) NaOH / 1.) EtOH, DMF, RT, 16 h, 2.) EtOH, DMF, 60 deg C, 24 h
  • 19
  • [ 128958-65-6 ]
  • 3-[5-(4-Benzyloxy-phenyl)-2-oxo-[1,3,4]oxadiazol-3-yl]-2-methyl-propionitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 76 percent / dioxane / 0.5 h 2: 1.) NaOH / 1.) EtOH, DMF, RT, 16 h, 2.) EtOH, DMF, 60 deg C, 24 h
  • 20
  • [ 128958-65-6 ]
  • 4-[5-(4-Benzyloxy-phenyl)-2-oxo-[1,3,4]oxadiazol-3-yl]-butyronitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 76 percent / dioxane / 0.5 h 2: 1.) NaOH / 1.) EtOH, DMF, RT, 16 h, 2.) EtOH, DMF, 60 deg C, 24 h
  • 21
  • [ 128958-65-6 ]
  • 3-[2-(4-Benzyloxy-phenyl)-5-thioxo-5,6-dihydro-[1,3,4]oxadiazin-4-yl]-propionitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 68 percent / ethanol / 48 h / Heating 2: 64 percent / CHCl3 / 0.5 h / Heating 3: 76 percent / P2S5, pyridine / 2 h / 60 °C
  • 22
  • [ 128958-65-6 ]
  • 5-[5-(4-Benzyloxy-phenyl)-2-oxo-[1,3,4]oxadiazol-3-yl]-pentanenitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 76 percent / dioxane / 0.5 h 2: 1.) NaOH / 1.) EtOH, DMF, RT, 16 h, 2.) EtOH, DMF, 60 deg C, 24 h
  • 23
  • [ 100-44-7 ]
  • [ 128958-65-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 1.) NaH / 1.) DMF, RT, 30 min, 2.) DMF, 5 h 2: 74 percent / hydrazine hydrate / propan-1-ol / 48 h / Heating
  • 24
  • [ 38870-89-2 ]
  • [ 128958-65-6 ]
  • [ 864177-85-5 ]
YieldReaction ConditionsOperation in experiment
With 4-methyl-morpholine In dichloromethane at 20℃; for 18h; 17 Preparation 17; 4-Benzvloxv-benzoic acid N'- (2-methoxy-acetvl)-hvdrazide; The product of preparation 16 (20g, 83mmol), methoxyacetyl chloride (8.2mL, 90mmol) and 4-methylmorpholine (16.4mL, 150mol) were dissolved in dichloromethane (250mL) and stirred at room temperature for 18 hours. The mixture was then diluted with dichloromethane/methanol (500mL, 90: 10) and washed with water. The organic phase was separated, dried over sodium sulfate and concentrated in vacuo to yield the title product, 17.5g. MS APCI+ m/z 315 [MH] +
  • 25
  • [ 128958-65-6 ]
  • Dihydrobenzocarbazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
With acetic acid In ethanol Hydrazone 19 in Scheme 5 Hydrazone 19 in Scheme 5 A solution consisting of 4-benzyloxyphenylhydrazide 18 (8 g, 37.3 mmol), 4-bezyloxytetralone 17 (11.3 g, 44.8 mmol), AcOH (5 drops) in EtOH (100 mL) was heated to reflux for 3 hours during which time all of the reactants went into solution. The reaction was cooled to 0° C. and the product precipitated out and was filtered out. The product 20 (9.5 g) was isolated as a white solid: mp 102-104° C. We found that the product was best used immediately because the products sitting out at room temperature results in discoloration.
With acetic acid In ethanol (Hydrazone 19 in Scheme 5) (Hydrazone 19 in Scheme 5) A solution consisting of 4-benzyloxyphenylhydrazide 18 (8 g, 37.3 mmol), 4-bezyloxytetralone 17 (11.3 g, 44.8 mmol), AcOH (5 drops) in EtOH (100 mL) was heated to reflux for 3 hours during which time all of the reactants went into solution. The reaction was cooled to 0° C. and the product precipitated out and was filtered out. The product 20 (9.5 g) was isolated as a white solid: mp 102-104° C. We found that the product was best used immediately because the products sitting out at room temperature results in discoloration.
  • 26
  • [ 128958-65-6 ]
  • [ 4637-24-5 ]
  • [ 956750-65-5 ]
YieldReaction ConditionsOperation in experiment
Stage #1: 4-benzyloxyphenylhydrazide; <i>N</i>,<i>N</i>-dimethyl-formamide dimethyl acetal With acetic acid In acetonitrile at 50℃; for 8h; Stage #2: With acetic acid In acetonitrile at 120℃; for 1h; 8 Preparation 8; 2-(4-(benzyloxy)phenyl)-1,3,4-oxadiazole; To a solution of 4-(benzyloxy)benzohydrazide (4.99 g) in acetonitrile (40 mL) was added N,N-dimethylformamide dimethyl acetal (2.68 g) and the reaction mixture heated at 50° C. for 8 h. 40 mL of Acetic acid was added and the reaction mixture was heated at 120° C. for 1 h. The reaction mixture was diluted with water and extracted with chloroform. The organic layer was washed with saturated sodium bicarbonate solution, dried with magnesium sulfate, filtered and concentrated to provide the title compound as a white solid 4.88 g. MS (AP+) m/e 163.1 (MH+).
  • 27
  • [ 128958-65-6 ]
  • [ 263021-30-3 ]
  • [ 1196987-72-0 ]
YieldReaction ConditionsOperation in experiment
With 2-chloro-1,3-dimethylimidazolinium chloride; triethylamine In dichloromethane for 2h; 6.1 EXAMPLE 64- { 5 r[3 -(2-fluoroethoxy)phenyl] -1,3 ,4-oxadiazol-2-yl } -N-methylaniline; Step 1 : To a solution of 4-benzyloxybenzoichydrazide (2 g, 8.26 mmol) and N-Boc-4- (methylamino)benzoic acid (2.074 g, 8.26 mmol) in CH2Cl2 (20.64 ml) was added Et3N (4.60 ml, 33.0 mmol) and 2-chloro-l,3-dimelhylimidazolimum chloride (2.76 g, 16.51 mmol). After 2 hs the reaction mixture was treated with 1 N HCl (10 mL) and extracted with EtOAc. The combined organics were dried (Na2SO4), filtered, and evaporated affording crude (4-[5-(3- benzyloxy-ρhenyl)-[l,3?4]oxadiazol-2-yl]-phenyl}-methyl-carbamic acid ter/-butyl ester which was used in the next step without further purification.
  • 29
  • [ 6344-05-4 ]
  • [ 128958-65-6 ]
  • [ 1207742-94-6 ]
YieldReaction ConditionsOperation in experiment
72% With acetic acid In ethanol for 1h; Reflux;
  • 30
  • [ 75-15-0 ]
  • [ 128958-65-6 ]
  • [ 741262-94-2 ]
YieldReaction ConditionsOperation in experiment
With potassium hydroxide In ethanol at 80℃; for 12h;
With potassium hydroxide In ethanol Reflux; 3.4. Synthesis of 5-(4-(Benzyloxy)phenyl)-1,3,4-oxadiazole-2(3H)-thione Equimolar quantities of the substituted benzohydrazide (5 mmol) and potassium hydroxide(5 mmol) were dissolved in 95% ethanol (20 mL). The mixture was allowed to stir for several minutesat room temperature and then carbon disulfide (15 mmol) was slowly added dropwise to the reactionsystem and the mixture was heated to reflux. The residue obtained was dissolved in water (50 mL) anddiluted hydrochloric acid was added to adjust the pH value of the solution to 5-6. The precipitate wascollected washed with water for several times and dried and recrystallized from ethanol. Colour: white;m.p. 160 °C.
With potassium hydroxide In ethanol at 85℃; for 3h;
  • 31
  • [ 100-44-7 ]
  • [ 128958-65-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: potassium carbonate; potassium iodide 2: hydrazine hydrate
Multi-step reaction with 2 steps 1.1: potassium hydroxide / acetonitrile / 0.5 h / Reflux 1.2: 3 h / Reflux 2.1: hydrazine hydrate / ethanol / 6 h / Reflux
Multi-step reaction with 2 steps 1: potassium carbonate / N,N-dimethyl-formamide / 4 h / 20 °C / Sonication 2: hydrazine hydrate / ethanol / 6 h / Reflux
Multi-step reaction with 2 steps 1: potassium carbonate / N,N-dimethyl-formamide / 4 h / Sonication 2: hydrazine hydrate / ethanol / 3 h / Sonication
Multi-step reaction with 2 steps 1: potassium carbonate 2: hydrazine hydrate

  • 32
  • [ 24424-99-5 ]
  • [ 128958-65-6 ]
  • [ 860298-66-4 ]
YieldReaction ConditionsOperation in experiment
In dichloromethane at 0 - 20℃; for 48h; 2 SYNTHESIS EXAMPLE 2; N-((5-(4-((3-fluorobenzyl)oxy)phenyl)-1,3,4-thiadiazol-2-yl)methyl)-2-oxo-8-phenyloctanamide Compound 128; Di-t-butyl dicarbonate (10.8 g, 49.5 mmol) was added to a solution of 4-(benzyloxy)benzohydrazide (10 g, 41.3 mmol) in dichloromethane (206 mL) at 0° C. The resulting mixture was stirred for 2 d at room temperature, then concentrated and the residue was triturated with diethyl ether to yield tert-butyl 2-(4-(benzyloxy)benzoyl)hydrazinecarboxylate. A mixture of tert-butyl 2-(4-(benzyloxy)benzoyl)hydrazinecarboxylate (13.7 g, 40 mmol) and Lawesson's reagent (8.1 g, 20.0 mmol) in THF (200 mL) THF was stirred for 2 d. Solvent was removed under vacuum and the residue was chromatographed (silica gel, heptane-ethyl acetate) to yield tert-butyl 2-(4-(benzyloxy)phenylcarbonothioyl)hydrazinecarboxylate. A solution of tert-butyl 2-(4-(benzyloxy)phenylcarbonothioyl)hydrazinecarboxylate(12 g) in 1,4-dioxane (34 mL) and 4.0 N HCl (34 mL) in 1,4-dioxane was stirred for 5 h. The resulting solid was collected and washed with diethyl ether to yield 4-(benzyloxy)benzothiohydrazide.
  • 33
  • [ 128958-65-6 ]
  • [ 142065-78-9 ]
  • [ 1369796-79-1 ]
YieldReaction ConditionsOperation in experiment
In methanol at 80℃; for 3h; sealed tube; 5 A solution of methyl 2-(((benzyloxy)carbonyl)amino)acetimidate (600 mg, 2.7 mmol) and 4-(benzyloxy)benzohydrazide (654 mg, 2.7 mmol) in methanol (45 mL) was heated at 80° C. in a sealed tube for 3 h. The solvent was removed under reduced pressure and the resulting residue was purified by chromatography (silica gel, heptane-ethyl acetate) to yield benzyl ((5-(4-(benzyloxy)phenyl)-1,3,4-oxadiazol-2-yl)methyl)carbamate. A solution of benzyl ((5-(4-(benzyloxy)phenyl)-1,3,4-oxadiazol-2-yl)methyl)carbamate (480 mg, 1.12 mmol) in 33% HBr in acetic acid (5 mL) was stirred for 1 h. Diethyl ether was added, and the supernatant was decanted. The process was repeated, and the resulting solid was collected by filtration to yield (5-(4-(benzyloxy)phenyl)-1,3,4-oxadiazol-2-yl)methanamine. A solution of (5-(4-(benzyloxy)phenyl)-1,3,4-oxadiazol-2-yl)methanamine (155 mg, 0.43 mmol), 7-(3-fluorophenoxy)-2-hydroxyheptanoic acid (110 mg, 0.43 mmol), 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide (99 mg, 0.52 mmol), DIPEA (0.224 mL, 1.3 mmol) and HOBt (70 mg, 0.52 mmol) in DMF (20 mL) was stirred overnight. The resulting mixture was diluted with NaHCO3 (saturated, aqueous) and extracted twice with ethyl acetate. The combined extracts were washed with brine, dried (Na2SO4) and concentrated to yield N-((5-(4-(benzyloxy)phenyl)-1,3,4-oxadiazol-2-yl)methyl)-7-(3-fluorophenoxy)-2-hydroxyheptanamide, which was in the next step used without further purification. To a solution of N-((5-(4-(benzyloxy)phenyl)-1,3,4-oxadiazol-2-yl)methyl)-7-(3-fluorophenoxy)-2-hydroxyheptanamide (190 mg, 0.37 mmol) in methylene chloride (5 mL) was added 1,1,1-tris(acetyloxy)1,1-dihydro-1,2-benziodoxol-3-(1H)-one (233 mg, 0.55 mmol) and the resulting mixture was stirred overnight, then quenched with excess sodium thiosulfate in saturated aqueous sodium bicarbonate. The mixture was then extracted twice with ethyl acetate and the combined organic extracts were washed with brine, dried (Na2SO4) and concentrated. The residue was purified by chromatography (silica gel, heptane-ethyl acetate) to yield the title compound. 1H NMR (400 MHz, CDCl3) δ 6.60-8.10 (overlapping m, 14H), 5.15 (s, 2H), 4.75-4.85 (m, 2H), 3.85-4.00 (m, 2H), 2.90-3.10 (m, 2H), 1.50-1.90 (m, 6H).
  • 34
  • [ 32315-10-9 ]
  • [ 128958-65-6 ]
  • [ 147807-38-3 ]
YieldReaction ConditionsOperation in experiment
In dichloromethane at 50℃; for 6h; Synthesis of 5-(4-alkoxy)-1,3,4-oxadiazol-2(3H)-one (4a-4u) To a stirred solution of 4-alkoxy benzoyl hydrazine (19.9mmol) in 20 mL CH2Cl2, a CH2Cl2 solution of triphosgene(2.95 g, 9.4 mmol) was added drop-wise and the reactionwas continued for 6 h at 50 °C. After the reaction completed(TLC monitoring), the solvent was removed under vacuum.The mixture was poured into 50 mL water and a solution of10% KOH was added to adjust the pH to 7-8. Aqueous layerwas extracted with dichloromethane (30 mL 3). The combinedlayers of dichloromethane were dried by anhydrousMgSO4, and the solvent was distilled off under reduced pressureto give a crude product.
  • 35
  • [ 75-15-0 ]
  • [ 128958-65-6 ]
  • C15H14N2O2S2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
In ethanol Reflux; 3.6. Synthetic method for oxadiazoles 1-27 General procedure: In the first step, sodium hydroxide (0.2 g) was added to a stirred mixture of substituted phenyl hydrazide (2.0 mmol) with carbon disulfide (2.0 mmol) in ethanolic condition. This reaction mixture was refluxed for 6-7 h and monitored by TLC until the reaction was complete. After completion of reaction, the mixture was allowed to cool in an ice bath and was neutralized by a 10%solution of hydrochloric acid, white precipitates of 2-mercaptooxadiazole were produced. In the next step, synthetic 2-mercaptooxadiazole (1.0 mmol) was added a few drops of triethylamine as a base, and stirred for 15 min, then added (1.0 mmol) substituted 2-bromoacetophenones, while the reaction mixture was refluxed for appropriate time. White precipitates were produced after a few minutes. It took 3 h for the completion of reaction(TLC analysis) and white precipitates were separated as S-substituted oxadiazoles, filtered, and washed with cold ethanol. The pure product was obtained in high yield (Scheme 1). The structures of all synthetic compounds were deduced by 1H NMR and EI-MS spectroscopy. All compounds gave satisfactory CHN analyses.
  • 36
  • [ 128958-65-6 ]
  • 5-(4-(benzyloxy)phenyl)-3-(((4-chloro-2-nitrophenyl)amino)methyl)-1,3,4-oxadiazole-2(3H)-thione [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: potassium hydroxide / ethanol / Reflux 2: 1 h / 20 °C / Molecular sieve; Sonication
  • 37
  • [ 128958-65-6 ]
  • 5-(4-(benzyloxy)phenyl)-3-(((4-bromophenyl)amino)methyl)-1,3,4-oxadiazole-2(3H)-thione [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: potassium hydroxide / ethanol / Reflux 2: 2 h / 20 °C / Molecular sieve; Sonication
  • 38
  • [ 128958-65-6 ]
  • 5-(4-(benzyloxy)phenyl)-3-(((2-nitrophenyl)amino)methyl)-1,3,4-oxadiazole-2(3H)-thione [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: potassium hydroxide / ethanol / Reflux 2: 1.5 h / 20 °C / Molecular sieve; Sonication
  • 39
  • [ 128958-65-6 ]
  • 5-(4-(benzyloxy)phenyl)-3-(((2,4-dinitrophenyl)amino)methyl)-1,3,4-oxadiazole-2(3H)-thione [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: potassium hydroxide / ethanol / Reflux 2: 1 h / 20 °C / Molecular sieve; Sonication
  • 40
  • [ 128958-65-6 ]
  • 5-(4-(benzyloxy)phenyl)-3-(morpholinomethyl)-1,3,4-oxadiazole-2(3H)-thione [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: potassium hydroxide / ethanol / Reflux 2: 1.5 h / 20 °C / Molecular sieve; Sonication
  • 41
  • [ 128958-65-6 ]
  • 5-(4-(benzyloxy)phenyl)-3-((phenylamino)methyl)-1,3,4-oxadiazole-2(3H)-thione [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: potassium hydroxide / ethanol / Reflux 2: 1.5 h / 20 °C / Molecular sieve; Sonication
  • 42
  • [ 128958-65-6 ]
  • 5-(4-(benzyloxy)phenyl)-3-(((4-methoxyphenyl)amino)methyl)-1,3,4-oxadiazole-2(3H)-thione [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: potassium hydroxide / ethanol / Reflux 2: 1 h / 20 °C / Molecular sieve; Sonication
  • 43
  • [ 128958-65-6 ]
  • 4-(((5-(4-(benzyloxy)phenyl)-2-thioxo-1,3,4-oxadiazol-3(2H)-yl)methyl)amino)benzoic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: potassium hydroxide / ethanol / Reflux 2: 2 h / 20 °C / Molecular sieve; Sonication
  • 44
  • [ 128958-65-6 ]
  • 5-(4-(benzyloxy)phenyl)-3-((methylamino)methyl)-1,3,4-oxadiazole-2(3H)-thione [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: potassium hydroxide / ethanol / Reflux 2: 2 h / 20 °C / Molecular sieve; Sonication
  • 45
  • [ 128958-65-6 ]
  • 5-(4-(benzyloxy)phenyl)-3-((biphenylamino)methyl)-1,3,4-oxadiazole-2(3H)-thione [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: potassium hydroxide / ethanol / Reflux 2: 2 h / 20 °C / Molecular sieve; Sonication
  • 46
  • [ 128958-65-6 ]
  • 5-(4-(benzyloxy)phenyl)-3-(piperazine-1-ylmethyl)-1,3,4-oxadiazole-2(3H)-thione [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: potassium hydroxide / ethanol / Reflux 2: 1.5 h / 20 °C / Molecular sieve; Sonication
  • 47
  • [ 128958-65-6 ]
  • 5-(4-(benzyloxy)phenyl)-3-(((4-chlorophenyl)amino)methyl)-1,3,4-oxadiazole-2(3H)-thione [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: potassium hydroxide / ethanol / Reflux 2: 1 h / 20 °C / Molecular sieve; Sonication
  • 48
  • [ 128958-65-6 ]
  • 3-((1H-1,2,4-triazol-1-yl)methyl) 5-(4-(benzyloxy)phenyl)-1,3,4-oxadiazole-2(3H)-thione [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: potassium hydroxide / ethanol / Reflux 2: 1.5 h / 20 °C / Molecular sieve; Sonication
  • 49
  • [ 128958-65-6 ]
  • C19H30O2 [ No CAS ]
  • 5α-Androstan-3β-ol-17-one 4-benzyloxybenzoylhydrazone [ No CAS ]
YieldReaction ConditionsOperation in experiment
73% With acetic acid In ethanol Reflux; General Method for Synthesizing 17-Hydrazono Derivatives of 5α-Androstan-3-ols 2-4. General procedure: A mixture of 1 (0.1 g,0.35 mmol) and the appropriate hydrazide (0.55 mmol) in EtOH (10 mL) with a catalytic amount of AcOH was refluxed for6-10 h and cooled to room temperature. The resulting precipitate was filtered off, rinsed with H2O and Et2O, dried, andcrystallized from EtOH.
  • 50
  • [ 1486-51-7 ]
  • [ 128958-65-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: sulfuric acid / Reflux 2: hydrazine hydrate / neat (no solvent) / 120 °C / Sealed tube
Multi-step reaction with 2 steps 1: sulfuric acid / Reflux 2: hydrazine hydrate / neat (no solvent) / 120 °C / Sealed tube
Multi-step reaction with 2 steps 1: sulfuric acid / 5 h / Reflux 2: hydrazine hydrate / ethanol / 100 °C / Sealed tube
Multi-step reaction with 2 steps 1: sulfuric acid / 5 h / Reflux 2: hydrazine hydrate / ethanol / 100 °C / Sealed tube

Reference: [1]Sevaille, Laurent; Gavara, Laurent; Bebrone, Carine; De Luca, Filomena; Nauton, Lionel; Achard, Maud; Mercuri, Paola; Tanfoni, Silvia; Borgianni, Luisa; Guyon, Carole; Lonjon, Pauline; Turan-Zitouni, Gülhan; Dzieciolowski, Julia; Becker, Katja; Bénard, Lionel; Condon, Ciaran; Maillard, Ludovic; Martinez, Jean; Frère, Jean-Marie; Dideberg, Otto; Galleni, Moreno; Docquier, Jean-Denis; Hernandez, Jean-François [ChemMedChem, 2017, vol. 12, # 12, p. 972 - 985]
[2]Baud, Damien; Bebrone, Carine; Becker, Katja; Benvenuti, Manuela; Cerboni, Giulia; Chelini, Giulia; Cutolo, Giuliano; De Luca, Filomena; Docquier, Jean-Denis; Feller, Georges; Fischer, Marina; Galleni, Moreno; Gavara, Laurent; Gresh, Nohad; Kwapien, Karolina; Legru, Alice; Mangani, Stefano; Mercuri, Paola; Pozzi, Cecilia; Sannio, Filomena; Sevaille, Laurent; Tanfoni, Silvia; Verdirosa, Federica; Berthomieu, Dorothée; Bestgen, Benoît; Frère, Jean-Marie; Hernandez, Jean-François [European Journal of Medicinal Chemistry, 2020, vol. 208]
[3]Gavara, Laurent; Legru, Alice; Verdirosa, Federica; Sevaille, Laurent; Nauton, Lionel; Corsica, Giuseppina; Mercuri, Paola Sandra; Sannio, Filomena; Feller, Georges; Coulon, Rémi; De Luca, Filomena; Cerboni, Giulia; Tanfoni, Silvia; Chelini, Giulia; Galleni, Moreno; Docquier, Jean-Denis; Hernandez, Jean-François [Bioorganic Chemistry, 2021, vol. 113]
[4]Legru, Alice; Verdirosa, Federica; Hernandez, Jean-François; Tassone, Giusy; Sannio, Filomena; Benvenuti, Manuela; Conde, Pierre-Alexis; Bossis, Guillaume; Thomas, Caitlyn A.; Crowder, Michael W.; Dillenberger, Melissa; Becker, Katja; Pozzi, Cecilia; Mangani, Stefano; Docquier, Jean-Denis; Gavara, Laurent [European Journal of Medicinal Chemistry, 2021, vol. 226]
  • 51
  • [ 364-73-8 ]
  • [ 128958-65-6 ]
  • 4-benzyloxy-N'-(4-bromo-2-nitrophenyl)benzhydrazide [ No CAS ]
YieldReaction ConditionsOperation in experiment
81% In dimethyl sulfoxide at 85℃; for 2h;
  • 52
  • [ 128958-65-6 ]
  • 3,6-bis{4-[4-(4-dodecyloxybenzoyloxy)benzoyloxy]phenyl}-1-phenyl-1,4-dihydrobenzo[e][1,2,4]triazin-4-yl [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1.1: dimethyl sulfoxide / 2 h / 85 °C 2.1: tin; acetic acid / 2.5 h / 20 - 120 °C 3.1: sodium periodate / dichloromethane; methanol / 20 °C 4.1: potassium carbonate; tetrakis(triphenylphosphine) palladium(0) / tetrahydrofuran; water / 24 h / Inert atmosphere; Reflux 5.1: tetrahydrofuran; dibutyl ether / 1.33 h / -10 - 20 °C / Inert atmosphere 5.2: 2 h / 20 °C 6.1: hydrogen; 5%-palladium/activated carbon / ethanol; tetrahydrofuran / 2585.81 Torr 6.2: 0.33 h 7.1: dmap / dichloromethane / 20 °C
  • 53
  • [ 128958-65-6 ]
  • 3,6-bis(4-hydroxyphenyl)-1-phenyl-1,4-dihydrobenzo[e][1,2,4]triazin-4-yl [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1.1: dimethyl sulfoxide / 2 h / 85 °C 2.1: tin; acetic acid / 2.5 h / 20 - 120 °C 3.1: sodium periodate / dichloromethane; methanol / 20 °C 4.1: potassium carbonate; tetrakis(triphenylphosphine) palladium(0) / tetrahydrofuran; water / 24 h / Inert atmosphere; Reflux 5.1: tetrahydrofuran; dibutyl ether / 1.33 h / -10 - 20 °C / Inert atmosphere 5.2: 2 h / 20 °C 6.1: hydrogen; 5%-palladium/activated carbon / ethanol; tetrahydrofuran / 2585.81 Torr 6.2: 0.33 h
  • 54
  • [ 128958-65-6 ]
  • 3-(4-benzyloxyphenyl)-6-(4-hydroxyphenyl)benzo[e][1,2,4]triazine [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: dimethyl sulfoxide / 2 h / 85 °C 2: tin; acetic acid / 2.5 h / 20 - 120 °C 3: sodium periodate / dichloromethane; methanol / 20 °C 4: potassium carbonate; tetrakis(triphenylphosphine) palladium(0) / tetrahydrofuran; water / 24 h / Inert atmosphere; Reflux
  • 55
  • [ 128958-65-6 ]
  • 3-(4-benzyloxyphenyl)-6-(4-hydroxyphenyl)-1-phenyl-1,4-dihydrobenzo[e][1,2,4]triazin-4-yl [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: dimethyl sulfoxide / 2 h / 85 °C 2.1: tin; acetic acid / 2.5 h / 20 - 120 °C 3.1: sodium periodate / dichloromethane; methanol / 20 °C 4.1: potassium carbonate; tetrakis(triphenylphosphine) palladium(0) / tetrahydrofuran; water / 24 h / Inert atmosphere; Reflux 5.1: tetrahydrofuran; dibutyl ether / 1.33 h / -10 - 20 °C / Inert atmosphere 5.2: 2 h / 20 °C
  • 56
  • [ 128958-65-6 ]
  • 3,6-bis(4-benzyloxyphenyl)benzo[e][1,2,4]triazine [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: dimethyl sulfoxide / 2 h / 85 °C 2: tin; acetic acid / 2.5 h / 20 - 120 °C 3: sodium periodate / dichloromethane; methanol / 20 °C 4: potassium carbonate; tetrakis(triphenylphosphine) palladium(0) / tetrahydrofuran; water / 24 h / Inert atmosphere; Reflux
  • 57
  • [ 128958-65-6 ]
  • 3-(4-benzyloxyphenyl)-6-bromobenzo[e][1,2,4]triazine [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: dimethyl sulfoxide / 2 h / 85 °C 2: tin; acetic acid / 2.5 h / 20 - 120 °C 3: sodium periodate / dichloromethane; methanol / 20 °C
  • 58
  • [ 128958-65-6 ]
  • 3-(4-benzyloxyphenyl)-6-{4-[4-(7,7,8,8,9,9,10,10,10-nonafluorodecyloxy)benzoyloxy]phenyl}-1-phenyl-1,4-dihydrobenzo[e][1,2,4]triazin-4-yl [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1.1: dimethyl sulfoxide / 2 h / 85 °C 2.1: tin; acetic acid / 2.5 h / 20 - 120 °C 3.1: sodium periodate / dichloromethane; methanol / 20 °C 4.1: potassium carbonate; tetrakis(triphenylphosphine) palladium(0) / tetrahydrofuran; water / 24 h / Inert atmosphere; Reflux 5.1: tetrahydrofuran; dibutyl ether / 1.33 h / -10 - 20 °C / Inert atmosphere 5.2: 2 h / 20 °C 6.1: dmap / dichloromethane / 2 h / 20 °C
  • 59
  • [ 128958-65-6 ]
  • 3-(4-hydroxyphenyl)-6-{4-[4-(7,7,8,8,9,9,10,10,10-nonafluorodecyloxy)benzoyloxy]phenyl}-1-phenyl-1,4-dihydrobenzo[e][1,2,4]triazin-4-yl [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1.1: dimethyl sulfoxide / 2 h / 85 °C 2.1: tin; acetic acid / 2.5 h / 20 - 120 °C 3.1: sodium periodate / dichloromethane; methanol / 20 °C 4.1: potassium carbonate; tetrakis(triphenylphosphine) palladium(0) / tetrahydrofuran; water / 24 h / Inert atmosphere; Reflux 5.1: tetrahydrofuran; dibutyl ether / 1.33 h / -10 - 20 °C / Inert atmosphere 5.2: 2 h / 20 °C 6.1: dmap / dichloromethane / 2 h / 20 °C 7.1: hydrogen; 5%-palladium/activated carbon / ethanol; tetrahydrofuran / 16 h / 2585.81 Torr 7.2: 1 h
  • 60
  • [ 128958-65-6 ]
  • 3,6-bis{4-[4-(7,7,8,8,9,9,10,10,11,11,12,12,12-tridecafluorododecyloxy)benzoyloxy]phenyl}benzo[e][1,2,4]triazine [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1: dimethyl sulfoxide / 2 h / 85 °C 2: tin; acetic acid / 2.5 h / 20 - 120 °C 3: sodium periodate / dichloromethane; methanol / 20 °C 4: potassium carbonate; tetrakis(triphenylphosphine) palladium(0) / tetrahydrofuran; water / 24 h / Inert atmosphere; Reflux 5: hydrogen; 5%-palladium/activated carbon / ethanol; tetrahydrofuran / 16 h / 2585.81 Torr 6: dmap / dichloromethane / 2 h / 20 °C
  • 61
  • [ 128958-65-6 ]
  • 3,6-bis(4-hydroxyphenyl)benzo[e][1,2,4]triazine [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: dimethyl sulfoxide / 2 h / 85 °C 2: tin; acetic acid / 2.5 h / 20 - 120 °C 3: sodium periodate / dichloromethane; methanol / 20 °C 4: potassium carbonate; tetrakis(triphenylphosphine) palladium(0) / tetrahydrofuran; water / 24 h / Inert atmosphere; Reflux 5: hydrogen; 5%-palladium/activated carbon / ethanol; tetrahydrofuran / 16 h / 2585.81 Torr
  • 62
  • [ 128958-65-6 ]
  • 3,6-bis{4-[4-(7,7,8,8,9,9,10,10,10-nonafluorodecyloxy)benzoyloxy]phenyl}-1-phenyl-1,4-dihydrobenzo[e][1,2,4]triazin-4-yl [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1.1: dimethyl sulfoxide / 2 h / 85 °C 2.1: tin; acetic acid / 2.5 h / 20 - 120 °C 3.1: sodium periodate / dichloromethane; methanol / 20 °C 4.1: potassium carbonate; tetrakis(triphenylphosphine) palladium(0) / tetrahydrofuran; water / 24 h / Inert atmosphere; Reflux 5.1: tetrahydrofuran; dibutyl ether / 1.33 h / -10 - 20 °C / Inert atmosphere 5.2: 2 h / 20 °C 6.1: hydrogen; 5%-palladium/activated carbon / ethanol; tetrahydrofuran / 2585.81 Torr 6.2: 0.33 h 7.1: dmap / dichloromethane / 20 °C
  • 63
  • [ 128958-65-6 ]
  • 3,6-bis{4-[4-(9,9,10,10,11,11,12,12,12-nonafluorododecyloxy)benzoyloxy]phenyl}-1-phenyl-1,4-dihydrobenzo[e][1,2,4]triazin-4-yl [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1.1: dimethyl sulfoxide / 2 h / 85 °C 2.1: tin; acetic acid / 2.5 h / 20 - 120 °C 3.1: sodium periodate / dichloromethane; methanol / 20 °C 4.1: potassium carbonate; tetrakis(triphenylphosphine) palladium(0) / tetrahydrofuran; water / 24 h / Inert atmosphere; Reflux 5.1: tetrahydrofuran; dibutyl ether / 1.33 h / -10 - 20 °C / Inert atmosphere 5.2: 2 h / 20 °C 6.1: hydrogen; 5%-palladium/activated carbon / ethanol; tetrahydrofuran / 2585.81 Torr 6.2: 0.33 h 7.1: dmap / dichloromethane / 20 °C
  • 64
  • [ 128958-65-6 ]
  • C20H16BrN3O [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: dimethyl sulfoxide / 2 h / 85 °C 2: tin; acetic acid / 2.5 h / 20 - 120 °C
  • 65
  • [ 128958-65-6 ]
  • 6-{4-[4-(7,7,8,8,9,9,10,10,10-nonafluorodecyloxy)benzoyloxy]phenyl}-1-phenyl-3-{4-[4-(7,7,8,8,9,9,10,10,11,11,12,12,12-tridecafluorododecyloxy)benzoyloxy]phenyl}-1,4-dihydrobenzo[e][1,2,4]triazin-4-yl [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 8 steps 1.1: dimethyl sulfoxide / 2 h / 85 °C 2.1: tin; acetic acid / 2.5 h / 20 - 120 °C 3.1: sodium periodate / dichloromethane; methanol / 20 °C 4.1: potassium carbonate; tetrakis(triphenylphosphine) palladium(0) / tetrahydrofuran; water / 24 h / Inert atmosphere; Reflux 5.1: tetrahydrofuran; dibutyl ether / 1.33 h / -10 - 20 °C / Inert atmosphere 5.2: 2 h / 20 °C 6.1: dmap / dichloromethane / 2 h / 20 °C 7.1: hydrogen; 5%-palladium/activated carbon / ethanol; tetrahydrofuran / 16 h / 2585.81 Torr 7.2: 1 h 8.1: dmap / dichloromethane / 20 °C
  • 66
  • [ 128958-65-6 ]
  • [ 123-08-0 ]
  • C21H18N2O3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With acetic acid In ethanol Sonication; (c) General procedure for the synthesis of 4-(benzyloxy)-N0-(substituted benzylidene) benzo hydrazide,called Schiff’s bases 5a-j: General procedure: Schiff’s bases 5a-j were obtained by condensation of equimolar quantities of 4-(benzyloxy) benzohydrazide (0.01 mol) and different substituted aldehydes (0.01 mol) in the presence of glacial aceticacid (0.02 mol) as a catalyst in absolute ethanol kept in an ultra-sonicator for 1 to 2 h. The completion ofthe reaction was monitored by TLC. The reaction mixture was concentrated and cooled. The obtainedsolid was filtered and dried. The product was recrystallized from ethanol.
  • 67
  • [ 128958-65-6 ]
  • [ 459-57-4 ]
  • C21H17FN2O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With acetic acid In ethanol Sonication; (c) General procedure for the synthesis of 4-(benzyloxy)-N0-(substituted benzylidene) benzo hydrazide,called Schiff’s bases 5a-j: General procedure: Schiff’s bases 5a-j were obtained by condensation of equimolar quantities of 4-(benzyloxy) benzohydrazide (0.01 mol) and different substituted aldehydes (0.01 mol) in the presence of glacial aceticacid (0.02 mol) as a catalyst in absolute ethanol kept in an ultra-sonicator for 1 to 2 h. The completion ofthe reaction was monitored by TLC. The reaction mixture was concentrated and cooled. The obtainedsolid was filtered and dried. The product was recrystallized from ethanol.
  • 68
  • [ 128958-65-6 ]
  • [ 99-61-6 ]
  • C21H17N3O4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With acetic acid In ethanol Sonication; (c) General procedure for the synthesis of 4-(benzyloxy)-N0-(substituted benzylidene) benzo hydrazide,called Schiff’s bases 5a-j: General procedure: Schiff’s bases 5a-j were obtained by condensation of equimolar quantities of 4-(benzyloxy) benzohydrazide (0.01 mol) and different substituted aldehydes (0.01 mol) in the presence of glacial aceticacid (0.02 mol) as a catalyst in absolute ethanol kept in an ultra-sonicator for 1 to 2 h. The completion ofthe reaction was monitored by TLC. The reaction mixture was concentrated and cooled. The obtainedsolid was filtered and dried. The product was recrystallized from ethanol.
  • 69
  • [ 128958-65-6 ]
  • [ 120-14-9 ]
  • C23H22N2O4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With acetic acid In ethanol Sonication; (c) General procedure for the synthesis of 4-(benzyloxy)-N0-(substituted benzylidene) benzo hydrazide,called Schiff’s bases 5a-j: General procedure: Schiff’s bases 5a-j were obtained by condensation of equimolar quantities of 4-(benzyloxy) benzohydrazide (0.01 mol) and different substituted aldehydes (0.01 mol) in the presence of glacial aceticacid (0.02 mol) as a catalyst in absolute ethanol kept in an ultra-sonicator for 1 to 2 h. The completion ofthe reaction was monitored by TLC. The reaction mixture was concentrated and cooled. The obtainedsolid was filtered and dried. The product was recrystallized from ethanol.
  • 70
  • [ 128958-65-6 ]
  • [ 121-33-5 ]
  • C22H20N2O4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With acetic acid In ethanol Sonication; (c) General procedure for the synthesis of 4-(benzyloxy)-N0-(substituted benzylidene) benzo hydrazide,called Schiff’s bases 5a-j: General procedure: Schiff’s bases 5a-j were obtained by condensation of equimolar quantities of 4-(benzyloxy) benzohydrazide (0.01 mol) and different substituted aldehydes (0.01 mol) in the presence of glacial aceticacid (0.02 mol) as a catalyst in absolute ethanol kept in an ultra-sonicator for 1 to 2 h. The completion ofthe reaction was monitored by TLC. The reaction mixture was concentrated and cooled. The obtainedsolid was filtered and dried. The product was recrystallized from ethanol.
  • 71
  • [ 121-32-4 ]
  • [ 128958-65-6 ]
  • C23H22N2O4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With acetic acid In ethanol Sonication; (c) General procedure for the synthesis of 4-(benzyloxy)-N0-(substituted benzylidene) benzo hydrazide,called Schiff’s bases 5a-j: General procedure: Schiff’s bases 5a-j were obtained by condensation of equimolar quantities of 4-(benzyloxy) benzohydrazide (0.01 mol) and different substituted aldehydes (0.01 mol) in the presence of glacial aceticacid (0.02 mol) as a catalyst in absolute ethanol kept in an ultra-sonicator for 1 to 2 h. The completion ofthe reaction was monitored by TLC. The reaction mixture was concentrated and cooled. The obtainedsolid was filtered and dried. The product was recrystallized from ethanol.
  • 72
  • [ 4397-53-9 ]
  • [ 128958-65-6 ]
  • C28H24N2O3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With acetic acid In ethanol Sonication; (c) General procedure for the synthesis of 4-(benzyloxy)-N0-(substituted benzylidene) benzo hydrazide,called Schiff’s bases 5a-j: General procedure: Schiff’s bases 5a-j were obtained by condensation of equimolar quantities of 4-(benzyloxy) benzohydrazide (0.01 mol) and different substituted aldehydes (0.01 mol) in the presence of glacial aceticacid (0.02 mol) as a catalyst in absolute ethanol kept in an ultra-sonicator for 1 to 2 h. The completion ofthe reaction was monitored by TLC. The reaction mixture was concentrated and cooled. The obtainedsolid was filtered and dried. The product was recrystallized from ethanol.
  • 73
  • [ 98-03-3 ]
  • [ 128958-65-6 ]
  • C19H16N2O2S [ No CAS ]
YieldReaction ConditionsOperation in experiment
With acetic acid In ethanol Sonication; (c) General procedure for the synthesis of 4-(benzyloxy)-N0-(substituted benzylidene) benzo hydrazide,called Schiff’s bases 5a-j: General procedure: Schiff’s bases 5a-j were obtained by condensation of equimolar quantities of 4-(benzyloxy) benzohydrazide (0.01 mol) and different substituted aldehydes (0.01 mol) in the presence of glacial aceticacid (0.02 mol) as a catalyst in absolute ethanol kept in an ultra-sonicator for 1 to 2 h. The completion ofthe reaction was monitored by TLC. The reaction mixture was concentrated and cooled. The obtainedsolid was filtered and dried. The product was recrystallized from ethanol.
  • 74
  • [ 41834-85-9 ]
  • [ 128958-65-6 ]
  • 1-(4-benzyloxybenzoyl)-4-propionylthiosemicarbazide [ No CAS ]
YieldReaction ConditionsOperation in experiment
54% In acetone at 70℃; 2 7.44 g (77 mmol) of potassium thiocyanate and 200 ml of acetone were placed in a 1000 ml three-necked flask, dissolved at room temperature, and then 6.49 ml (74 mmol) of propionyl chloride was added dropwise thereto, after the reaction was completed.15 g (62 mmol) of 4-benzyloxybenzoyl hydrazide and 300 ml of acetone were heated and refluxed at 70 ° C. After the reaction was completed, the reaction mixture was dried to give a yellow solid.Recrystallization from methanol gave 12 g (yield: 54%) as a white solid.
  • 75
  • [ 100-39-0 ]
  • [ 128958-65-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: potassium iodide; potassium carbonate / acetonitrile / 60 °C 2: hydrazine hydrate / methanol / Reflux
Multi-step reaction with 2 steps 1: potassium carbonate / acetone / 10 h / Reflux 2: hydrazine hydrate / ethanol / 16 h / Reflux
  • 76
  • [ 128958-65-6 ]
  • [ 1196986-80-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 2-chloro-1,3-dimethylimidazolinium chloride; triethylamine / dichloromethane / 2 h 2: ammonium formate; acetic acid / palladium 10% on activated carbon / methanol / 20 °C 3: di-isopropyl azodicarboxylate
  • 77
  • [ 128958-65-6 ]
  • [ 263021-30-3 ]
  • [ 1196987-74-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 2-chloro-1,3-dimethylimidazolinium chloride; triethylamine / dichloromethane / 2 h 2: ammonium formate; acetic acid / palladium 10% on activated carbon / methanol / 20 °C
  • 78
  • [ 1677-47-0 ]
  • [ 128958-65-6 ]
  • C22H15Cl2N3O3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
70% With acetic acid; In ethanol; at 20℃;Reflux; General procedure: A mixture of 4-(chlorobenzyloxy)benzoylhydrazines (0.01 mol) and <strong>[1677-47-0]4,5-dichloroindolin-2,3-dione</strong>s (0.01 mol) in ethanol (70 ml) containing 3-4 drops of glacial acetic acid was refluxed for 1-2 hr and left overnight at room temperature. The solid product so obtained was filtered, washed with methanol and recrystallised from aq. DMF. Compounds 1b-5b were synthesized using same method and gave satisfactory analysis for C, H and N. 1a: IR (KBr) cm-1 : 3441, 3187 (NH), 1702, 1669 (C=O), 1606 (C=N), 1252 (-CH2O), 765 (C-Cl), 1H NMR (DMSO-d6): delta ppm : 5.15 (2H, s, -CH2O), 6.95-8.13 (11H, m, ArH), 10.85 (1H, s, CONH), 13.91 (1H, s, CONH). [Found : C, 59.94, H, 3.37, N, 9.52 C22H15Cl2N3O3 requires C, 60.02, H, 3.43, N, 9.54%].
  • 79
  • [ 1677-48-1 ]
  • [ 128958-65-6 ]
  • C22H15Cl2N3O3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
83% With acetic acid; In ethanol; at 20℃;Reflux; General procedure: A mixture of 4-(chlorobenzyloxy)benzoylhydrazines (0.01 mol) and 4,5-dichloroindolin-2,3-diones (0.01 mol) in ethanol (70 ml) containing 3-4 drops of glacial acetic acid was refluxed for 1-2 hr and left overnight at room temperature. The solid product so obtained was filtered, washed with methanol and recrystallised from aq. DMF. Compounds 1b-5b were synthesized using same method and gave satisfactory analysis for C, H and N.
  • 80
  • [ 128958-65-6 ]
  • 2-isothiocyanato-4-methoxybenzo[d]thiazole [ No CAS ]
  • 2-(4-(benzyloxy)benzoyl)-N-(4-methoxybenzo[d]thiazol-2-yl)hydrazinecarbothioamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 70℃; for 2h; 5-(4-(benzyloxy)phenyl)-N-(4-methoxybenzo[djthiazol-2-yl)-1,3,4-oxadiazol-2- amine (7b) To a suspension of 2-isothiocyanato-4-methoxybenzo[djthiazole 4 (15.0 g, cmde, 60.0 mmol) in DMF (150 mL) was added DIPEA (21 mL, 15.5 g, 120.0 mmol) dropwise. The suspension turned homogeneous and brown. Then 4- (benzyloxy)benzohydrazide 5b (15.3 g, 63.0 mmol) was added in portions and theresulting solution was heated to 70 °C for 2 h. LCMS showed the starting material was consumed completely and desired product 2-(4-(benzyloxy)benzoyl)-N-(4- methoxybenzo[djthiazol-2-yl)hydrazinecarbothioamide 6b was formed. LC-MS [M+Hj 431; After cooling to room temperature, pyridine (14.2 g, 180.0 mmol) and TsC1 (17.2 g, 90.0 mmol) was added in portions and the solution was heated to 70 °Cfor 2 h. The above solution was concentrated under vacuum. The residue was added MeOH (100 mL) and stirred for 10 mm. The resulting suspension was filtered. The filter cake was washed with MeOH, EA and TBME in turn. The filter cake was collected and dried to afford the desired product 5-(4-(benzyloxy)phenyl)-N-(4- methoxybenzo[djthiazol-2-yl)-1,3,4-oxadiazol-2-amine 7b (9.0 g, 35% yield). LCMS(TOF-ESI) for C23H18N403S, calculated for [M+Hj: 431.1170, found for [M+Hj:.
  • 81
  • [ 96202-56-1 ]
  • [ 128958-65-6 ]
  • C24H21N3O3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
70% With acetic acid In ethanol Reflux; 3-[4-(Chlorobenzyloxy)-benzohydrazono]-5-ethylisatins (1-5) General procedure: A mixture of an appropriate 4-(chlorobenzyloxy)benzohydrazide (0.01 mol) and 5-ethylisatin (0.01 mol) in ethanol (70 mL) containing 2-3 drops of glacial acetic acid was refluxed for 2-3 h and left overnight at room temperature. The solid so obtained was filtered and washed with methanol. 1. IR (KBr, cm-1): 3441, 3188, 1702, 1606, 1245, PMR (DMSO-d6): δ 1.21 (3H, t, J=7.6 Hz, CH2CH3), 2.58 (2H, q, J=7.6 Hz, CH2CH3), 5.15 (2H, s, -CH2O), 6.95-8.10 (m, 12H, ArH), 10.77 (1H, s, CONH), 13.58 (1H, s, NHCO).
  • 82
  • [ 128958-65-6 ]
  • 1-acetyl-5-ethylisatin [ No CAS ]
  • C26H23N3O4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
60% With acetic acid In ethanol Reflux; 1-Acetyl-3-[4-(chlorobenzyloxy)-benzohydrazono]-5-ethylisatins (6-10) General procedure: A mixture of an appropriate 4-(chlorobenzyloxy)benzohydrazide (0.01 mol) and 1-acetyl-5-ethylisatin (0.01 mol) in ethanol (70 mL) containing 2-3 drops of glacial acetic acid was refluxed for 4-5 h and left overnight at room temperature. The solid so obtained was filtered and washed with methanol. 6. IR (KBr, cm-1): 3367, 1678, 1664, 1598, 1244, PMR (DMSO-d6): δ 1.21 (3H, t, J 7.6 Hz, CH2CH3), 2.32 (3H, s, COMe), 2.58 (2H, q, J=7.6 Hz, CH2CH3), 5.39 (2H, s,-CH2O-), 6.98-8.05 (12H, m, Ar-H), 13.65 (1H, s, CONH).
  • 83
  • [ 128958-65-6 ]
  • 9-(methoxycarbonyl)-2-(4-(benzyloxy)phenyl)[1,2,4]triazino[5,6,1-kl]phenoxazin-3-yl [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: dimethyl sulfoxide / 10 h / 100 °C 2.1: tin; acetic acid / 2 h / 20 - 120 °C 2.2: 0.5 h / 20 °C 3.1: dimethyl sulfoxide / 50 °C / Inert atmosphere 4.1: tert.-butylnitrite / benzene / 3.25 h / 20 - 70 °C
  • 84
  • [ 128958-65-6 ]
  • 9-(hydroxycarbonyl)-2-(4-(benzyloxy)phenyl)[1,2,4]triazino[5,6,1-kl]phenoxazin-3-yl [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: dimethyl sulfoxide / 10 h / 100 °C 2.1: tin; acetic acid / 2 h / 20 - 120 °C 2.2: 0.5 h / 20 °C 3.1: dimethyl sulfoxide / 50 °C / Inert atmosphere 4.1: tert.-butylnitrite / benzene / 3.25 h / 20 - 70 °C 5.1: potassium hydroxide / tetrahydrofuran; methanol / 3 h / 60 °C 5.2: pH 1
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