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[ CAS No. 5785-06-8 ]

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Chemical Structure| 5785-06-8
Chemical Structure| 5785-06-8
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CAS No. :5785-06-8 MDL No. :MFCD00007601
Formula : C8H10N2O2 Boiling Point : -
Linear Structure Formula :- InChI Key :N/A
M.W :166.18 g/mol Pubchem ID :-
Synonyms :

Safety of [ 5785-06-8 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P301+P312-P302+P352-P304+P340-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 5785-06-8 ]

  • Downstream synthetic route of [ 5785-06-8 ]

[ 5785-06-8 ] Synthesis Path-Downstream   1~17

  • 1
  • [ 5368-81-0 ]
  • [ 5785-06-8 ]
YieldReaction ConditionsOperation in experiment
93% With hydrazine hydrate monohydrate In ethanol for 7h; Reflux;
93% With hydrazine hydrate monohydrate In ethanol; lithium hydroxide monohydrate at 80℃; for 24h;
90% With hydrazine hydrate monohydrate In ethanol Reflux; 1.1 Part 1- Synthesis of 3-Methoxybenzohydrazide To a solution of methyl 3-methoxybenzoate (5.0 g, 30.1 mmol, 1.00 equiv) in EtOH (50 mL) was added hydrazine hydrate (80%, 9.4 g, 150 mmol, 5.00 equiv). The reaction was refluxed overnight, then concentrated under vacuum. The residue solidified upon standing at rt. The solid was triturated with hexane (100 mL) and the resulting solid separated and dried to yield 4.5 g (90%) of the desired product as a white solid.
86% With hydrazine monohydrate In ethanol for 0.266667h; Reflux; Microwave irradiation;
85% With hydrazine In methanol for 3h; Reflux;
With hydrazine hydrate monohydrate
With hydrazine In ethanol for 12h; Heating;
With hydrazine hydrate monohydrate
With hydrazine In lithium hydroxide monohydrate at 60℃;
With hydrazine hydrate monohydrate In ethanol at 70℃; for 3h;
With hydrazine hydrate monohydrate In methanol Reflux;
With hydrazine hydrate monohydrate In ethanol Reflux; General procedure for the synthesis of the hydrazide ligands General procedure: Different substituted carboxylic acids (20 mmol) (A) were stirred with thionyl chloride (100 mmol) in dry methanol (75 ml) or 5-6 h to synthesize corresponding methyl esters (B) (Scheme1). After extraction of esters in chloroform, solvent was evaporated and esters (66 mmol) were refluxed with hydrazine hydrate(330 mmol) in ethanol (75 ml) for 4-5 h. A solid was obtained upon removal of the solvent by rotary evaporation. The resulting solid was washed with hexane to afford hydrazide ligand (C). The spectral and analytical data are given below.
With hydrazine hydrate monohydrate In methanol
With hydrazine hydrate monohydrate In methanol for 5h; Reflux; General procedure: Compounds 6a-t were synthesized from substituted benzoic acid via six steps according to the literature method as described. Various substituted benzoic acids 1a-t were treated with SOCl2 to give compounds 2a-t, which were reacted with CH3OH and EtN3 in CH2Cl2 at 0 to afford compounds 3a-t. Compounds 4a-t were prepared by the reaction of compounds 3a-t, hydrazine hydrate in CH3OH under reflux condition about 5h. Subsequently, compounds 5a-t were obtained by reaction of compounds 4a-t with CS2 and KOH in CH3OH. Compounds 6a-t were obtained by the cyclization reaction of compounds 5a-t in the presence of HCl at 0-5°C.
With hydrazine hydrate monohydrate In ethanol Reflux;
With hydrazine hydrate monohydrate
With hydrazine hydrate monohydrate In methanol at 65 - 67℃; for 9h;
With hydrazine hydrate monohydrate Cooling with ice; Reflux; General procedure for synthesis of hydrazides (5a-l)1 General procedure: Carboxylic acids (10 mmol) were refluxed for 1-2 h in methanol (5 mL) in presence of conc. H2SO4 (catalytic amount) with continuous stirring. The reaction was monitored by TLC till the acids were fully converted to the corresponding esters [Eluent: EtOAc/Hexanes (1:4)]. The reaction mixture was allowed to cool down to room temperature and hydrazine monohydrate 80% (40 mmol, 1.91 mL) was added slowly in an ice bath. The reaction was then warmed to room temperature and refluxed for another 1-2 h and followed by TLC till formation of hydrazide. The reaction mixture was kept at refrigerator till the product precipitated. All hydrazides were isolated in quantitative yields and in a pure form. There melting points were in full agreement with the literature melting points of the same compounds.
With hydrazine hydrate monohydrate In methanol at 85℃; for 14h;
With hydrazine hydrate monohydrate In methanol Reflux; Inert atmosphere; 2.1.1. General procedure for the synthesis of hydrazides 2 General procedure: Hydrazine hydrate (5 mL, 40%) was added to a solution of requiredester (5.0 mmol) in methanol (20 mL). The solution was refluxed for12-24 h and monitored by TLC until starting material was completelyconsumed. After that, solvent was evaporated under reduced pressureand a small amount of water (5 mL) was added to precipitate the hydrazide,which was filtered and dried in vacuum to give a shiny white toyellow solid in excellent yields, without further purification.
With hydrazine hydrate monohydrate In methanol at 0 - 20℃; for 4h; 4.3 General procedure for the synthesis of compounds 3a-3q General procedure: Compound 2a was dissolved in methanol and the mixture was cooled in an ice bath. Hydrazine hydrate (3 eq.) was added dropwise at 0°C. The resulting reaction mixture was stirred at room temperature for 4h. The reaction progress was monitored by TLC (MeOH/DCM=1:20) until it was completed. A crude solid 3a was obtained by filtering and washing with ice methanol, which was used to the next step without further purification. Preparation method of 3b∼3q was same as 3a.
With hydrazine hydrate monohydrate In ethanol Reflux; Synthesis of benzohydrazide derivatives (4a-m) General procedure: Method A Methyl benzoate derivatives (2, 1 eq) and 85% hydrazine hydrate (10 eq) were dissolved in ethanol (45 mL). The mixture was refluxed overnight. After cooling, the solvent was removed in vacuo and the residue was separated on the Biotage SNAP Cartridge KP-Sil 100 g eluting with 0-60 % ethyl acetate/petroleum ether to afford compound 4.
With hydrazine monohydrate In methanol Reflux;
With hydrazine hydrate monohydrate In ethanol at 90℃;

Reference: [1]Karabanovich, Galina; Zemanová, Júlia; Smutný, Tomáš; Székely, Rita; Šarkan, Michal; Centárová, Ivana; Vocat, Anthony; Pávková, Ivona; Čonka, Patrik; Němeček, Jan; Stolaříková, Jiřina; Vejsová, Marcela; Vávrová, Kateřina; Klimešová, Věra; Hrabálek, Alexandr; Pávek, Petr; Cole, Stewart T.; Mikušová, Katarína; Roh, Jaroslav [Journal of Medicinal Chemistry, 2016, vol. 59, # 6, p. 2362 - 2380]
[2]Barreiro, Eliezer J.; Noël, François G.; Pedreira, Júlia Galvez Bulhões; Silva, Rafaela Ribeiro [Molecules, 2021, vol. 26, # 23]
[3]Current Patent Assignee: LYCERA CORPORATION - WO2016/138335, 2016, A1 Location in patent: Paragraph 00215
[4]Zaheer, Muhammad; Zia-Ur-Rehman, Muhammad; Rahman, Salma; Ahmed, Naveed; Chaudhary, Muhammad Nawaz [Journal of the Chilean Chemical Society, 2012, vol. 57, # 4, p. 1492 - 1496]
[5]Popiołek, Łukasz; Biernasiuk, Anna [Journal of Enzyme Inhibition and Medicinal Chemistry, 2016, vol. 31, p. 62 - 69]
[6]Hutton [Journal of Organic Chemistry, 1955, vol. 20, p. 855,858]
[7]Skoumbourdis, Amanda P.; Huang, Ruili; Southall, Noel; Leister, William; Guo, Vicky; Cho, Ming-Hsuang; Inglese, James; Nirenberg, Marshall; Austin, Christopher P.; Xia, Menghang; Thomas, Craig J. [Bioorganic and Medicinal Chemistry Letters, 2008, vol. 18, # 4, p. 1297 - 1303]
[8]Palmer, James T.; Hirschbein, Bernard L.; Cheung, Harry; McCarter, John; Janc, James W.; Yu, Z. Walter; Wesolowski, Gregg [Bioorganic and Medicinal Chemistry Letters, 2006, vol. 16, # 11, p. 2909 - 2914]
[9]Rando, Daniela G.; Avery, Mitchell A.; Tekwani, Babu L.; Khan, Shabana I.; Ferreira, Elizabeth I. [Bioorganic and Medicinal Chemistry, 2008, vol. 16, # 14, p. 6724 - 6731]
[10]Kümmerle, Arthur E.; Schmitt, Martine; Cardozo, Suzana V. S.; Lugnier, Claire; Villa, Pascal; Lopes, Alexandra B.; Romeiro, Nelilma C.; Justiniano, Hélène; Martins, Marco A.; Fraga, Carlos A. M.; Bourguignon, Jean-Jacques; Barreiro, Eliezer J. [Journal of Medicinal Chemistry, 2012, vol. 55, # 17, p. 7525 - 7545]
[11]Rafiq, Muhammad; Saleem, Muhammad; Hanif, Muhammad; Maqsood, Muhammad Rizwan; Rama, Nasim Hasan; Lee, Ki-Hwan; Seo, Sung-Yum [Bulletin of the Korean Chemical Society, 2012, vol. 33, # 12, p. 3943 - 3949]
[12]Ain, Qurrat Ul; Ashiq, Uzma; Jamal, Rifat Ara; Mahrooof-Tahir, Mohammad [Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 2013, vol. 115, p. 683 - 689]
[13]Li, Pei; Yin, Juan; Xu, Weiming; Wu, Jian; He, Ming; Hu, Deyu; Yang, Song; Song, Baoan [Chemical Biology and Drug Design, 2013, vol. 82, # 5, p. 546 - 556]
[14]Li, Liangjing; Ding, Hao; Wang, Baogang; Yu, Shichong; Zou, Yan; Chai, Xiaoyun; Wu, Qiuye [Bioorganic and Medicinal Chemistry Letters, 2014, vol. 24, # 1, p. 192 - 194]
[15]Qurrat-Ul-Ain; Rasheed, Saima; Mahroof-Tahir, Mohammad; Ashiq, Uzma; Jamal, Rifat Ara; Khurshid, Sumaira; Mustafa, Sana [Journal of the Chemical Society of Pakistan, 2016, vol. 38, # 5, p. 864 - 881]
[16]Jasiak, Karolina; Kudelko, Agnieszka; Zieliński, Wojciech; Kuźnik, Nikodem [Arkivoc, 2016, vol. 2017, # 2, p. 87 - 106]
[17]Ganesh Kumar; Gautham Shenoy; Kar, Sidhartha Sankar; Shenoy, Vishnu; Bairy, Indira [Pharmaceutical Chemistry Journal, 2018, vol. 51, # 10, p. 907 - 917]
[18]Goher, Shaimaa S.; Griffett, Kristine; Hegazy, Lamees; Elagawany, Mohamed; Arief, Mohamed M.H.; Avdagic, Amer; Banerjee, Subhashis; Burris, Thomas P.; Elgendy, Bahaa [Bioorganic and Medicinal Chemistry Letters, 2019, vol. 29, # 3, p. 449 - 453]
[19]Kahl, Dylan J.; Hutchings, Kim M.; Lisabeth, Erika Mathes; Haak, Andrew J.; Leipprandt, Jeffrey R.; Dexheimer, Thomas; Khanna, Dinesh; Tsou, Pei-Suen; Campbell, Phillip L.; Fox, David A.; Wen, Bo; Sun, Duxin; Bailie, Marc; Neubig, Richard R.; Larsen, Scott D. [Journal of Medicinal Chemistry, 2019, vol. 62, # 9, p. 4350 - 4369]
[20]Chen, Lixia; Gao, Suyu; Li, Hua; Li, Mingxue; Li, Xingzhou; Liu, Yang; Wu, Canrong; Yang, Kaiyin; Zhang, Yujie; Zheng, Mengzhu [Bioorganic Chemistry, 2020, vol. 96]
[21]Zhou, Wenjuan; Xu, Chenhao; Dong, Guanjun; Qiao, Hui; Yang, Jing; Liu, Hongmin; Ding, Lina; Sun, Kai; Zhao, Wen [European Journal of Medicinal Chemistry, 2021, vol. 217]
[22]Lin, Lin; Lin, Guangyao; Zhou, Qingtong; Bathgate, Ross A.D.; Gong, Grace Qun; Yang, Dehua; Liu, Qing; Wang, Ming-Wei [Bioorganic Chemistry, 2021, vol. 110]
[23]Maniak, Halina; Talma, Michał; Giurg, Mirosław [International Journal of Molecular Sciences, 2021, vol. 22, # 22]
[24]Chen, Chong-Hao; Fang, Ze-Yu; Lv, Peng-Cheng; Ni, Lei-Qiang; Sun, Juan; Wu, Yuan-Feng; Zhang, Yi-Heng; Zheng, Qi [Chemistry and biodiversity, 2022]
  • 2
  • [ 5785-06-8 ]
  • [ 134-81-6 ]
  • [ 110249-07-5 ]
YieldReaction ConditionsOperation in experiment
87% Stage #1: benzil With N,N,N’,N’-tetrabromobenzene-1,3-disulfonamide In neat (no solvent) at 100℃; for 0.05h; Stage #2: 3-methoxybenzoic hydrazide With ammonium acetate In neat (no solvent) at 100℃; for 3.58h;
With ammonium acetate; acetic acid
  • 3
  • [ 75-15-0 ]
  • [ 5785-06-8 ]
  • Potassium 2-(3-methoxybenzoyl) hydrazine-1-carbodithioate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: 3-methoxybenzoic hydrazide With potassium hydroxide In ethanol at 20℃; for 1h; Stage #2: carbon disulfide In ethanol
With potassium hydroxide In ethanol at 20℃; for 12h;
With potassium hydroxide In ethanol at 20℃; for 12h;
With potassium hydroxide In methanol at 0 - 5℃; Synthesis of 3-Substituted 4-Amino-5-aryl-3H-1,2,4-triazole-3-thiones 5a-j. Potassium hydroxide (0.125 mol) was dissolved in dry methanol (50 mL). To the solution, aryl acid hydrazide 3a-j (0.125 mol) was added and cooled the solution in ice. To this, carbon disulfide (0.125 mol) was added in small portions with constant stirring. The solid product of potassium dithiocarbazate 4a-j was formed, filtered, washed with chilled diethyl ether, dried and was taken in water (20 mL) and hydrazine hydrate (0.250 mol) was added, and followed by refluxed for 10-12 h. The reaction mixture turned to green with evolution of hydrogensulfide and finally it became homogeneous. It was then poured in ice and acidified with 37% hydrochloric acid. The white precipitates was filtered, washed with cold water and recrystallized from aqueous methanol.
With potassium hydroxide In methanol at 20℃; Reflux; General procedure: Compounds 6a-t were synthesized from substituted benzoic acid via six steps according to the literature method as described. Various substituted benzoic acids 1a-t were treated with SOCl2 to give compounds 2a-t, which were reacted with CH3OH and EtN3 in CH2Cl2 at 0 to afford compounds 3a-t. Compounds 4a-t were prepared by the reaction of compounds 3a-t, hydrazine hydrate in CH3OH under reflux condition about 5h. Subsequently, compounds 5a-t were obtained by reaction of compounds 4a-t with CS2 and KOH in CH3OH. Compounds 6a-t were obtained by the cyclization reaction of compounds 5a-t in the presence of HCl at 0-5°C.
With potassium hydroxide In ethanol at 20℃;
12.4 g With potassium hydroxide In ethanol at 0℃; for 0.25h; 16.2 (2) The compound 3 - methoxy benzoyl hydrazine 8 g and 3 g of potassium hydroxide dissolved in 30 ml ethanol stirring,Add 1.3 mL of carbon disulfide,The above solution was allowed to react at 0 ° C for 15 minutes, a solid appeared,Filtered and dried to give the compound potassium salt 12.4 g;Take 8 g of potassium salt, add 30 mL of water,Then add 1.5 mL of hydrazine hydrate,The solution was reacted at 100 ° C for 5 hours, and after the completion of the reaction,The reaction solution was poured into ice water, adjusted to neutral with 5 mol / L hydrochloric acid,A solid appeared, filtered, and dried to yield 5.1 g of compound VIII in 80% yield.
With potassium hydroxide In methanol at 0℃; General procedure: Potassium hydroxide (0.125 mol, 1eq) was dissolved in drymethanol (50 mL). To the solution, substituted acid hydrazides 3(0.125 mol, 1eq) was added and cooled the solution in ice. To this,carbon disulfide (0.125 mol, 1eq) was added with constant stirringfor 1e2 h. The solid product of potassium salt of hydrazinecarbodithioates5 formed, was filtered, washed with chilled diethyl etherand dried. It was directly used for next step without further purification.The potassium salt of hydrazinecarbodithioates 5 wastaken in deionized water (50 mL) and hydrazine hydrate(0.250 mol) was added, followed by reflux overnight. The reactionmixture turned to yellowish green with evolution of hydrogensulfide and finally it became homogeneous. It was then poured incrushed ice and neutralized with hydrochloric acid to afford whiteprecipitates of substituted triazole derivatives 6 which was filtered,washed with cold water and crystallized on methanol.
With potassium hydroxide In methanol at 25℃; 4.1.1 General synthetic procedure for the key intermediates 7 General procedure: The substituted hydrazides 5 (10mmol) were stirred with potassium hydroxide (15mmol) in absolute methanol. Then CS2 (12mmol) was slowly added and the mixture was stirred at 25°C for 1-6h. After the reaction completed, the solid was precipitated and dried to afford compounds 6. The compounds 6 was refluxed with excess 80% hydrazine hydrate in water under microwave irradiation at 250W, 100°C, for 60min. After completion of the reaction, the mixture was acidified with concentrated HCl and the precipitate solid was filtered, washed with water, dried and recrystallized from aqueous methanol to obtain the intermediates 7.
With potassium hydroxide In methanol at 0℃; Synthesis of 4-amino-5-aryl-4H-1,2,4-triazole-3-thiol (6) General procedure: Potassium hydroxide (0.56 g, 10 mmol) was added to a solution ofaryl hydrazide 4 (10 mmol) in methanol (25 mL) at 0 °C with stirring.Carbon disulfide (0.5 mL) was then added slowly and the reactionmixture was stirred and monitored by TLC. After reaction completion,the solid product potassium dithiocarbazinate 5 was filtered, washedwith chilled methanol and dried. Without any purification, potassiumdithiocarbazinate 5 was dissolved in water (20 mL) and hydrazinehydrate (1 mL) was added. The mixture was heated under reflux untilthe reaction was complete, and then diluted with a little cold water andacidified with conc. hydrochloric acid. The white precipitated solid 6was filtered, washed with cold water and recrystallised from aqueous methanol.
With potassium hydroxide In ethanol at 20 - 25℃; for 3h; 6.c c: Dissolve the hydrazide obtained in b in anhydrous ethanol, add dropwise an anhydrous ethanol solution containing 1.0g KOH after it is completely dissolved, slowly add CS2 until a white solid is produced, the amount of CS2 is 1.5mL. After reacting at 20-25°C for 3 hours, it was filtered off with suction and washed with absolute ethanol several times.

Reference: [1]Sarva, Maria Concetta; Romeo, Giuseppe; Guerrera, Francesco; Siracusa, Mariangela; Salerno, Loredana; Russo, Filippo; Cagnotto, Alfredo; Goegan, Mara; Mennini, Tiziana [Bioorganic and Medicinal Chemistry, 2002, vol. 10, # 2, p. 313 - 323]
[2]Skoumbourdis, Amanda P.; Huang, Ruili; Southall, Noel; Leister, William; Guo, Vicky; Cho, Ming-Hsuang; Inglese, James; Nirenberg, Marshall; Austin, Christopher P.; Xia, Menghang; Thomas, Craig J. [Bioorganic and Medicinal Chemistry Letters, 2008, vol. 18, # 4, p. 1297 - 1303]
[3]Location in patent: scheme or table Baeeri, Maryam; Foroumadi, Alireza; Motamedi, Maryam; Yahya-Meymandi, Azadeh; Firoozpour, Loghman; Ostad, Seyed N.; Shafiee, Abbas; Souzangarzadeh, Saeid; Abdollahi, Mohammad [Chemical Biology and Drug Design, 2011, vol. 78, # 3, p. 438 - 444]
[4]Rafiq, Muhammad; Saleem, Muhammad; Hanif, Muhammad; Maqsood, Muhammad Rizwan; Rama, Nasim Hasan; Lee, Ki-Hwan; Seo, Sung-Yum [Bulletin of the Korean Chemical Society, 2012, vol. 33, # 12, p. 3943 - 3949]
[5]Li, Liangjing; Ding, Hao; Wang, Baogang; Yu, Shichong; Zou, Yan; Chai, Xiaoyun; Wu, Qiuye [Bioorganic and Medicinal Chemistry Letters, 2014, vol. 24, # 1, p. 192 - 194]
[6]Karabanovich, Galina; Zemanová, Júlia; Smutný, Tomáš; Székely, Rita; Šarkan, Michal; Centárová, Ivana; Vocat, Anthony; Pávková, Ivona; Čonka, Patrik; Němeček, Jan; Stolaříková, Jiřina; Vejsová, Marcela; Vávrová, Kateřina; Klimešová, Věra; Hrabálek, Alexandr; Pávek, Petr; Cole, Stewart T.; Mikušová, Katarína; Roh, Jaroslav [Journal of Medicinal Chemistry, 2016, vol. 59, # 6, p. 2362 - 2380]
[7]Current Patent Assignee: JIANGSU OCEAN UNIVERSITY - CN106008623, 2016, A Location in patent: Paragraph 0047
[8]Rafiq, Muhammad; Saleem, Muhammad; Jabeen, Farukh; Hanif, Muhammad; Seo, Sung-Yum; Kang, Sung Kwon; Lee, Ki Hwan [Journal of Molecular Structure, 2017, vol. 1138, p. 177 - 191]
[9]Xu, Qile; Sun, Maolin; Bai, Zhaoshi; Wang, Yueting; Wu, Yue; Tian, Haiqiu; Zuo, Daiying; Guan, Qi; Bao, Kai; Wu, Yingliang; Zhang, Weige [European Journal of Medicinal Chemistry, 2017, vol. 139, p. 242 - 249]
[10]Liu, Xiu-Jian; Wang, Lei; Yin, Long; Cheng, Feng-Chang; Sun, Hui-Min; Liu, Wei-Wei; Shia, Da-Hua; Caoa, Zhi-Ling [Journal of Chemical Research, 2017, vol. 41, # 10, p. 571 - 575]
[11]Current Patent Assignee: NORTHWESTERN UNIVERSITY (ILLINOIS) - CN112125860, 2020, A Location in patent: Paragraph 0112; 0117
  • 4
  • [ 5785-06-8 ]
  • [ 3697-66-3 ]
  • 1-[<i>N</i>'-(3-methoxy-benzoyl)-hydrazinocarbonyl]-cyclopropanecarboxylic acid ethyl ester [ No CAS ]
  • 5
  • [ 5785-06-8 ]
  • [ 380151-85-9 ]
  • (CH3)4C2O2BC6H4CHNNHCOC6H4OCH3 [ No CAS ]
  • 6
  • [ 1711-05-3 ]
  • [ 5785-06-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: Et3N / CH2Cl2 / 2 h 2: 37percent aq. HCl / 0.5 h
With hydrazine hydrate; triethylamine In acetonitrile for 3h; Reflux; 2.3. Synthesis of aralkanoic acid hydrazides 3 General procedure: Aralkanoic acid chlorides 2 were synthesized by the reaction ofaralkanoic acids 1 (1 mmol) in the presence of 1,2edichloroethane(12 mL) solvent and phosphorous oxychloride (0.4 mL) as chlorinatingagent under reflux for 3 h. Then, the resulting solution wascooled to room temperature, and the solvent was removed underreduced pressure to afford aralkanoic acid chlorides 2, which wasdirectly used in the next step without further purification. Aralkanoicacid chlorides 2 was dissolved in acetonitrile (80 mL), addeddrop wise to a solution containing hydrazine hydrate (1 mmol), TEA(0.5 mL) and acetonitrile (20 mL) and allowed to reflux for 3 h withmonitoring by TLC. After consumption of the starting material, thereaction mixture was cooled to room temperature. Evaporation ofthe solvent under reduced pressure yielded crude substituted aromaticacid hydrazides 3 as a white solid on cooling, which waspurified by column chromatography and crystallized on methanol.
With hydrazine hydrate In dichloromethane at 20℃; General procedure: Method B Substituted benzoyl chloride (3, 1 eq) and 85% hydrazine hydrate (2 eq) were dissolved in dichloromethane (25 mL). The mixture was stirred at room temperature overnight. The progress was monitored by TLC and the terminated by addition of water. The mixture was extracted with dichloromethane, washed with water and dried over anhydrous Na2SO4. After filtration, the solvent was removed in vacuo and the residue was separated on the Biotage SNAP Cartridge KP-Sil 100 g eluting with 0-60% ethyl acetate/petroleum ether to afford compound 4.
Multi-step reaction with 2 steps 1: sulfuric acid / 5 h / 60 °C 2: hydrazine hydrate / 12 h / 80 °C

  • 7
  • [ 532-54-7 ]
  • [ 5785-06-8 ]
  • N'-(2-(hydroxyimino)-1-phenylethylidene)-3-methoxybenzohydrazide [ No CAS ]
YieldReaction ConditionsOperation in experiment
32% With sulfuric acid In methanol for 16h; Heating / reflux; 3 General Procedure X The relevant hydrazide of formula II as described herein (2.4 mmol) was dissolved in MeOH (10 mL) and cooled to 0°C. Two drops of concentrated sulfuric acid were added followed by dropwise addition of the relevant oxime of formula III as described herein (2 mmol) dissolved in MeOH (10 mL). The reaction was heated at reflux for 16 h. The product could be isolated by chromatography or, if a precipitate is formed during the reaction, this could be filtered off, washed with MeOH and recrystallised from MeOH/water. Example 3 '- (2-(Hydroxyimino)-1-phenylethylidene)-3-methoxybenzohydrazide General procedure X was employed to give the title compound as a white crystalline solid in 32% isolated yield. 1H-NMR (300 MHz, DMSO-d6) No. 13. 05 (s, 1H), 12.60 (s, 1H), 8.51 (s, 1H), 7.77-7. 76 (m, 2H), 7.51-7. 41 (m, 6H), 7.23-7. 20 (m, 1H), 3.85 (s, 3H).
  • 8
  • [ 5785-06-8 ]
  • [ 149-73-5 ]
  • [ 5378-30-3 ]
YieldReaction ConditionsOperation in experiment
93% With Al3+-K10 montmorillonite clay In neat (no solvent) at 55℃; for 0.25h; Microwave irradiation; General procedure for 1,3,4-oxadiazole synthesis General procedure: A 5 mL microwave vial was charged with acidhydrazide (100 mg, 1 eq), trimethyl orthoester (2 eq) and Al3+-K10 clay (75 mg). The resulting mixture was kept under microwave irradiation maintaining the temperature at 55 °C for 15 min (Microwave irradiations were performed on CEM-discover model No. 908010). The reaction was monitored by TLC. After completion of the reaction, reaction mixture was diluted with ethyl acetate stirred well, filtered, washed well with ethyl acetate. Filtrate was evaporated under reduced pressure to obtain highly pure product. In some cases, products were purified by column chromatography using 60-120 mesh silica with 20-100 % ethyl acetate in pet ether as eluting solvents. The catalyst recovered by filtration was reused for another 5 more times.
  • 9
  • [ 5785-06-8 ]
  • [ 453-71-4 ]
  • 4-(3-nitro-4-fluorophenyl)-1-(3-methoxybenzoyl)semicarbazide [ No CAS ]
YieldReaction ConditionsOperation in experiment
93% With diphenyl phosphoryl azide; triethylamine In acetonitrile at 120℃;
  • 10
  • [ 10259-22-0 ]
  • [ 5785-06-8 ]
YieldReaction ConditionsOperation in experiment
100% With hydrazine hydrate; In ethanol; water;Reflux; EXAMPLE 5; 4-[5-(3-methoxyphenyD- 1 ,3,4-oxadiazol:2-yl]-N-methylaniline; Step 1: To a solution of ethyl 3-methoxy benzoate (1.0 g, 5.55 mmol) in EtOH (11 mL) was added 80% hydrazine in water (1.09 mL, 27.7 mmol), and the resulting solution was heated to reflux overnight. The reaction mixture was then cooled to room temperature and the volatiles were removed in vacuo to afford 3-methoxy-benzoic acid hydrazide (920 mg, 5.55 mmol, 100% yield) which was used without further purification. ES MS (M+H+) = 167.
84% With hydrazine hydrate; In ethanol; water;Reflux; General procedure: Hydrazides (30-58) were synthesized by one pot conventionalmethod24 Benzoic acid or its derivative (10 mmol) was dissolvedin ethanol (20 mL). Sulfuric acid (3 N, 2 mL) was added and thereaction contents were refluxed for six hours. The reaction wasmonitored with TLC. After the completion of the reaction, the reactionmixture was neutralized by adding solid NaHCO3, and filteredto remove excess of NaHCO3. In the neutralized reaction mixture which contains ethyl ester, hydrazine monohydrate (1.5 mL,3 mmol) was added and refluxed for 3-6 h to complete the reaction.Ethanol and unreacted hydrazine were removed by distillationupto 1/3 volume. The reaction contents were cooled, filteredand recrystallized from methanol to obtain the desired hydrazidecrystals (see Supporting information).
With hydrazine hydrate; In ethanol;Reflux; General procedure: Hydrazide ligands (1-12) were synthesized by reportedmethod [28,29]. Ethylbenzoate (25 mmol) was dissolved inethanol (75 mL), and then hydrazine hydrate (100 mmol)was added and the mixture refluxed for 5 h. The solid obtainedwas washed with hexane to afford the hydrazide.Other ligands were prepared from their respective esters. Theanalytical data of benzohydrazide (1), M.P. 116 C; 2-fluorobenzohydrazide (2), M.P. 74 C; 2-methoxybenzohydrazide(3), M.P. 83 C; 2-aminobenzohydrazide (4), M.P.124 C; 4-phenylsemicarbazide (5), M.P. 125 C; 3-aminobenzohydrazide(6), M.P. 79C; 4-aminobenzohydrazide (7),M.P. 229 C; 3-methoxybenzohydrazide (8), M.P. 94 C; 3-fluorobenzohydrazide (9), M.P. 138 C; 3-iodobenzohydrazide(10), M.P. 141 C; 4-iodobenzohydrazide (11) M.P.170 C and 3-bromobenzohydrazide (12) M.P. 160 C; werereported previously [28,30].
With hydrazine hydrate; In ethanol; for 5h;Reflux; General procedure: 5mL of hydrazine monohydrate (80%) was added to a solution of intermediate 3 (5mmol) in ethanol (5mL). The reaction mixture was maintained under reflux for 5h. was then concentrated under reduced pressure and the resulting solid was collected by filtration, washed with cold water and dried to give the desired intermediate 4 as a white solid.

  • 11
  • [ 10541-83-0 ]
  • [ 5785-06-8 ]
  • [ 1196986-64-7 ]
YieldReaction ConditionsOperation in experiment
26% With 2-chloro-1,3-dimethylimidazolinium chloride; triethylamine In dichloromethane at 20℃; 5.2 Step 2: To a solution of 3-methoxy-benzoic acid hydrazide (100 mg, 0.60 mmol) and 4- methylamino-benzoic acid (91 mg, 0.60 mmol) in CH2Cl2 (1.5 mL) at room temperature was added El3N (0.34 mL, 2.41 mmol) followed by 2-chloro-l,3-dimethylimidazolinium chloride (201 mg, 1.20 mmol) causing a slightly exothermal reaction. The resulting mixture was allowed to stir overnight at room temperature before the volatiles were removed in vacuo and purified by reversed phase HPLC to afford 4-[5-(3-methoxyphenyl)-l,3,4-oxadiazol-2-yl]-N-methylaniline (44 mg, 0.16 mmol 26% yield). ES MS (M+H+) = 282; 1H NMR (499 MHz, DMSO): δ 7.85 (2 H, d, J = 8.61 Hz), 7.66 (1 H9 d, J - 7.69 Hz), 7.58 (1 H, t, J = 1.92 Hz), 7.53 (1 H, t, J = 7.98 Hz)5 7.19 (1 H, dd, J - 8.29, 2.62 Hz), 6.69 (2 H, d, J = 8.61 Hz), 6.55 (1 H, q, J = 5.00 Hz), 3.87 (3 H, s), 2.76 (3 H, d, J - 5.01 Hz); HRMS m/z 282.1227 (C16Hi5N3O2 + H+ requires 282.1237).
  • 12
  • [ 5785-06-8 ]
  • [ 1259052-00-0 ]
  • [ 1259051-85-8 ]
YieldReaction ConditionsOperation in experiment
65.4% With triethylamine In ethanol at 20 - 60℃; for 72h; 15.7; 16.7 Step 7: Synthesis of 4-[N'-(3-Methoxy-benzoyl)-hydrazino]-7-methyl-2-oxo-1,5-diphenyl-1,2,5,8-tetrahydro-pyrido[2,3-d]pyrimidine-6-carboxylic acid ethyl ester [Show Image] The compound of step 6 (100 mg, 0.237 mmol) was taken in 2 ml EtOH and treated successively with m-anisic hydrazide (99.6 mg, 0.6 mmol) and TEA (Triethylamine) (35 microl, 0.25 mmol) at room temperature and stirred at 60 °C for 72 h. The reaction mixture was partitioned between water (25 ml) and DCM (30 ml). The organic phase was separated and the solvent was evaporated under vacuum at 40 °C. The product was purified with HPLC on a RP-18 column (Sphinx, 21 mm x 250 mm, 5 microm, Macherey-Nagel) with a gradient 30-100% MeCN with 0.02% HCOOH in 22 min and a flow rate of 21 ml/min yielding a light yellow solid (85.5 mg, 0.155 mmol, 65.4%).
  • 13
  • [ 75-15-0 ]
  • [ 5785-06-8 ]
  • [ 108413-55-4 ]
YieldReaction ConditionsOperation in experiment
87% With potassium hydroxide In ethanol for 38h; Reflux;
86% With N,N-dimethyl-formamide for 18h; Sonication; Green chemistry;
64% In N,N-dimethyl-formamide at 40 - 70℃; Inert atmosphere; 4.10 4.1.2. General procedure for synthesis of 5-substituted 1,3,4-oxadiazole-2-thiols General procedure: To a solution of acid hydrazide in anhydrous 5-15mL of DMF, carbon disulfide (2.5mL/mmol) was added at room temperature and under a nitrogen atmosphere. The reaction mixture was then heated to 40°C for 15min and then to 70°C for 4-8h until the reaction was completed. After completion, the reaction mixture was cooled to room temperature and poured dropwise into ice cold water. The solids formed were separated by filtration, washed with water and dried in vacuo.
With potassium hydroxide In ethanol
In ethanol for 5h; Reflux;
Stage #1: carbon disulfide; 3-methoxybenzoic hydrazide With potassium hydroxide In ethanol Reflux; Stage #2: With hydrogenchloride In ethanol; water
With potassium hydroxide In ethanol Reflux;
With potassium hydroxide In ethanol for 20h; Reflux;
With triethylamine In methanol at 65 - 67℃; for 10h;
Stage #1: carbon disulfide; 3-methoxybenzoic hydrazide With potassium hydroxide In ethanol Stage #2: With hydrogenchloride In water
With potassium hydroxide In ethanol; water at 95℃; for 16h; Inert atmosphere;
Stage #1: 3-methoxybenzoic hydrazide With potassium hydroxide In ethanol for 0.166667h; Inert atmosphere; Stage #2: carbon disulfide In ethanol Reflux; Stage #3: In water at 70 - 80℃; 4.1.2 General synthetic procedure for the key intermediate 5(a-c): General procedure: The intermediate 5(a-c) were synthesized by two step reaction. Firstly, to a 100mL flask was added the intermediate compound 3(a-b) (1mmol) and milled potassium hydroxide (1.1mmol) in ethanol (5mL), stirred for 10min under nitrogen atmosphere. Later, slowly added carbon disulphide (2mmol) to the reaction mixture, solid will observed (if necessary, add ethanol) and heated to reflux for 4-5 h. The reaction progress was detected by using TLC technique. After completion of the reaction, the reaction mass was cooled to room temperature and concentrated under reduced pressure to afford a crude solid 4(a-d). The obtained crude solid was taken as such for further step. (0029) The obtained crude intermediate 4(a-d) was taken in water and heated to reflux at 70-80°C for 7-8 h. After completion of the reaction, the reaction mixture was gradually brought to room temperature followed cooled to 0 to 5°C. Then neutralised with 10% hydrochloric acid solution, the precipitated solid was filtered, and several times washed with cold water. The obtained solid was dried and used as it is for next step.
With potassium hydroxide In ethanol for 12h; Reflux;

Reference: [1]Karabanovich, Galina; Zemanová, Júlia; Smutný, Tomáš; Székely, Rita; Šarkan, Michal; Centárová, Ivana; Vocat, Anthony; Pávková, Ivona; Čonka, Patrik; Němeček, Jan; Stolaříková, Jiřina; Vejsová, Marcela; Vávrová, Kateřina; Klimešová, Věra; Hrabálek, Alexandr; Pávek, Petr; Cole, Stewart T.; Mikušová, Katarína; Roh, Jaroslav [Journal of Medicinal Chemistry, 2016, vol. 59, # 6, p. 2362 - 2380]
[2]Yarmohammadi, Elahe; Beyzaei, Hamid; Aryan, Reza; Moradi, Ashraf [Molecular Diversity, 2021, vol. 25, # 4, p. 2367 - 2378]
[3]Kummari, Lalith K.; Butler, Mark S.; Furlong, Emily; Blundell, Ross; Nouwens, Amanda; Silva, Alberto B.; Kappler, Ulrike; Fraser, James A.; Kobe, Bostjan; Cooper, Matthew A.; Robertson, Avril A.B. [Bioorganic and Medicinal Chemistry, 2018, vol. 26, # 20, p. 5408 - 5419]
[4]Location in patent: scheme or table Zareefa, Muhammad; Iqbal, Rashid; Zaidi, Javid Hussain; Arfan, Muhammad; Ali, Muhammad; Khan, Khalid M. [Letters in Organic Chemistry, 2010, vol. 7, # 5, p. 411 - 414]
[5]Deora, Girdhar Singh; Karthikeyan, Chandrabose; Moorthy, N. S. Hari Narayana; Rathore, Vandana; Rawat, Arun K.; Tamrakar, Akhilesh K.; Srivastava; Trivedi, Piyush [Medicinal Chemistry Research, 2013, vol. 22, # 11, p. 5344 - 5348]
[6]Li, Pei; Yin, Juan; Xu, Weiming; Wu, Jian; He, Ming; Hu, Deyu; Yang, Song; Song, Baoan [Chemical Biology and Drug Design, 2013, vol. 82, # 5, p. 546 - 556]
[7]Ahmed, Muhammad Naeem; Yasin, Khawaja Ansar; Hameed, Shahid; Ayub, Khurshid; Haq, Ihsan-ul; Tahir, M. Nawaz; Mahmood, Tariq [Journal of Molecular Structure, 2017, vol. 1129, p. 50 - 59]
[8]Wang, Zi-Zhen; Sun, Wen-Xue; Wang, Xue; Zhang, Ya-Han; Qiu, Han-Yue; Qi, Jin-Liang; Pang, Yan-Jun; Lu, Gui-Hua; Wang, Xiao-Ming; Yu, Fu-Gen; Yang, Yong-Hua [Chemical Biology and Drug Design, 2017, vol. 90, # 2, p. 236 - 243]
[9]Ganesh Kumar; Gautham Shenoy; Kar, Sidhartha Sankar; Shenoy, Vishnu; Bairy, Indira [Pharmaceutical Chemistry Journal, 2018, vol. 51, # 10, p. 907 - 917]
[10]Wang, Pei-Yi; Wang, Ming-Wei; Zeng, Dan; Xiang, Meng; Rao, Jia-Rui; Liu, Qing-Qing; Liu, Li-Wei; Wu, Zhi-Bing; Li, Zhong; Song, Bao-An; Yang, Song [Journal of Agricultural and Food Chemistry, 2019, vol. 67, # 13, p. 3535 - 3545]
[11]Kahl, Dylan J.; Hutchings, Kim M.; Lisabeth, Erika Mathes; Haak, Andrew J.; Leipprandt, Jeffrey R.; Dexheimer, Thomas; Khanna, Dinesh; Tsou, Pei-Suen; Campbell, Phillip L.; Fox, David A.; Wen, Bo; Sun, Duxin; Bailie, Marc; Neubig, Richard R.; Larsen, Scott D. [Journal of Medicinal Chemistry, 2019, vol. 62, # 9, p. 4350 - 4369]
[12]Vanjare, Balasaheb D.; Choi, Nam Gyu; Mahajan, Prasad G.; Raza, Hussain; Hassan, Mubashir; Han, Yohan; Yu, Seon-Mi; Kim, Song Ja; Seo, Sung-Yum; Lee, Ki Hwan [Bioorganic and Medicinal Chemistry, 2021, vol. 41]
[13]Cheng, Wanqing; Fan, Jiangping; Guo, Yong; Han, Meiyue; Ma, Nannan; Yan, Xiaoting; Yang, Ruige [Journal of Agricultural and Food Chemistry, 2021, vol. 69, # 51, p. 15544 - 15553]
  • 14
  • [ 5785-06-8 ]
  • C12H6ClN3O4 [ No CAS ]
  • [ 1296210-40-6 ]
YieldReaction ConditionsOperation in experiment
With dmap In dichloromethane at 0 - 20℃; for 36.5h; 4.1.2. General procedure for the synthesis of N'-substituted-2-(5-nitrofuran or 5-nitrothiophen-2-yl)-3H-benzo[d]imidazole-5-carbohydrazide derivatives 5a-i, 6a-i General procedure: A mixture of 3a,b (0.3 mmol), thionyl chloride (1.5 mmol), and benzene 25 mL was gradually heated to boiling, whereupon the acid chloride dissolved. After refluxing for 12 h, excess of thionyl chloride and solvent were removed in vacuo. The acid chloride was not characterized, then to a solution of acid chloride, DMAP (1.5 mmol) in dry CH2Cl2 (10 mL) was slowly added a dry CH2Cl2 (10 mL) solution of carbohydrazide respective (0.4 mmol) (30 min) at 0 °C, and the mixture was stirred for 36 h at rt. The solvent was removed in vacuo and the residue was slowly added water 5% KOH at 0 °C and the mixture stirred for 30 min. The solid was washed with water, methanol and ethyl ether, recrystallized from a mixture of ethanol and water (1:1) to give 5a-i, 6a-i.
  • 15
  • [ 5785-06-8 ]
  • C12H6ClN3O3S [ No CAS ]
  • [ 1296210-49-5 ]
YieldReaction ConditionsOperation in experiment
With dmap In dichloromethane at 0 - 20℃; for 36.5h; 4.1.2. General procedure for the synthesis of N'-substituted-2-(5-nitrofuran or 5-nitrothiophen-2-yl)-3H-benzo[d]imidazole-5-carbohydrazide derivatives 5a-i, 6a-i General procedure: A mixture of 3a,b (0.3 mmol), thionyl chloride (1.5 mmol), and benzene 25 mL was gradually heated to boiling, whereupon the acid chloride dissolved. After refluxing for 12 h, excess of thionyl chloride and solvent were removed in vacuo. The acid chloride was not characterized, then to a solution of acid chloride, DMAP (1.5 mmol) in dry CH2Cl2 (10 mL) was slowly added a dry CH2Cl2 (10 mL) solution of carbohydrazide respective (0.4 mmol) (30 min) at 0 °C, and the mixture was stirred for 36 h at rt. The solvent was removed in vacuo and the residue was slowly added water 5% KOH at 0 °C and the mixture stirred for 30 min. The solid was washed with water, methanol and ethyl ether, recrystallized from a mixture of ethanol and water (1:1) to give 5a-i, 6a-i.
  • 16
  • [ 5785-06-8 ]
  • [ 635-93-8 ]
  • [ 351366-73-9 ]
YieldReaction ConditionsOperation in experiment
83% In methanol at 20℃; for 0.5h; Synthesis of H2L1 5-Chlorosalicylaldehyde (1.0 mmol, 0.16 g) and 3-methoxybenzohydrazide (1.0 mmol, 0.17 g)were dissolved in methanol (30 mL) with stirring. The mixture was stirred for about 30 min at room temperature to give colorless solution. The solution was left still in air to slow evaporate of most of the solvent, to give crystalline product of H2L2. The product was isolated by filtration and washed with cold methanol. Yield, 83%; m.p. 181.0-182.5 °C. Analysis: found: C 59.23%,H 4.26%, N 9.07%; calculated for C15H13ClN2O3: C 59.12%, H 4.30%, N 9.19%. IR data (cm-1,KBr): 3447 (w), 3195 (w), 1653 (s), 1611 (m), 1589 (m), 1561 (m), 1494 (s), 1435 (s), 1357(w), 1332 (w), 1301 (w), 1267 (m), 1153 (s), 1114 (m), 1080 (s), 1035 (m), 996 (m), 853 (s),781 (w), 745 (w), 727 (w), 546 (w), 470 (w). 1H NMR (300 MHz, d6-DMSO): 12.41 (s, 1H),11.72 (s, 1H), 8.61 (s, 1H), 7.85 (t, 1H), 7.60 (m, 2H), 7.38 (d, 1H), 7.19 (d, 1H), 6.91 (d, 1H),6.85 (s, 1H), 3.79 (s, 3H). 13C NMR (75 MHz, d6-DMSO): 164.03, 161.54, 158.37, 145.71,134.10, 132.82, 129.88, 128.75, 121.63, 120.70, 119.53, 117.37, 116.86, 112.45, 55.71.
82% In methanol for 2h; Reflux;
  • 17
  • [ 5785-06-8 ]
  • [ 1364195-36-7 ]
  • [ 1364195-45-8 ]
YieldReaction ConditionsOperation in experiment
67% In butan-1-ol at 130℃; for 24h; Inert atmosphere; 6.2. General procedure for the preparation of triazolo-benzodiazepines 4a-e General procedure: Thiolactam 2 (1.0 equiv) and carboxylic acid hydrazide 3a-e (2.0 equiv) were dissolved in n-butanol and heated to 130 °C in a sealed vial under nitrogen atmosphere for 24 h. The reaction mixture was cooled to room temperature and stirred with an aqueous glucose solution for 2 h. The crude product was extracted several times with dichloromethane. The combined organic layers were washed with water, dried over sodium sulfate, filtered and evaporated. Purification was done by flash column chromatography (dichloromethane/methanol, 9:1), giving the triazolo-benzodiazepines 4a-e in 17-67% yield.
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