Home Cart 0 Sign in  

[ CAS No. 41491-54-7 ] {[proInfo.proName]}

,{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]}
Chemical Structure| 41491-54-7
Chemical Structure| 41491-54-7
Structure of 41491-54-7 * Storage: {[proInfo.prStorage]}
Cart0 Add to My Favorites Add to My Favorites Bulk Inquiry Inquiry Add To Cart

Quality Control of [ 41491-54-7 ]

Related Doc. of [ 41491-54-7 ]

Alternatived Products of [ 41491-54-7 ]

Product Details of [ 41491-54-7 ]

CAS No. :41491-54-7 MDL No. :MFCD06655273
Formula : C8H5ClN2OS Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W : 212.66 Pubchem ID :-
Synonyms :

Safety of [ 41491-54-7 ]

Signal Word: Class:
Precautionary Statements: UN#:
Hazard Statements: Packing Group:

Application In Synthesis of [ 41491-54-7 ]

* 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 [ 41491-54-7 ]

[ 41491-54-7 ] Synthesis Path-Downstream   1~5

  • 1
  • [ 75-15-0 ]
  • [ 1673-47-8 ]
  • [ 41491-54-7 ]
YieldReaction ConditionsOperation in experiment
95% With aluminum oxide; potassium hydroxide In ethanol for 0.116667h; Microwave irradiation; 10 General procedure for the synthesis of 5-substituted-1,3,4-oxadiazole-2-thione (1-12) General procedure: A mixture of respective hydrazide (10 mmol), potassiumhydroxide (0.56 g, 10 mmol) and alumina were finely ground in aglove box with a mortar and pestle. Then carbon disulfide(1.2 mL, 20 mmol) was added to this mixture in a Pyrex glass vial,which was placed in a screw-capped thick-walled Teflon vessel.Microwave-irradiation (MW domestic type oven 900W with a frequency2450 MHz, Dawlance, Pakistan) was applied for 7 min.After the completion of reaction (TLC analysis), ethanol was addedinto reaction mixture and filtered. Filtrate was evaporated; distilledwater was added to semi-solid material and acidified withhydrochloric acid to pH = 4. Precipitates so obtained were filteredand dried to afford off white solid compound 2a-r and then recrystallizedfrom ethanol:water (50:50) mixture.
52% With potassium hydroxide In ethanol for 3h; Heating;
With potassium hydroxide In ethanol at 85℃; for 3h;
With potassium hydroxide In ethanol at 85℃; for 3h; - 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 potassium hydroxide

Reference: [1]Shahzad, Sohail Anjum; Yar, Muhammad; Bajda, Marek; Shahzadi, Lubna; Khan, Zulfiqar Ali; Naqvi, Syed Ali Raza; Mutahir, Sadaf; Mahmood, Nasir; Khan, Khalid Mohammed [Bioorganic Chemistry, 2015, vol. 60, p. 37 - 41]
[2]Charistos; Vagenas; Tzavellas; Tsoleridis; Rodios [Journal of Heterocyclic Chemistry, 1994, vol. 31, # 6, p. 1593 - 1598]
[3]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]
[4]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]
[5]Abid, Aisha; Eijaz, Sana; Lateef, Mehreen; Qurrat-ul-Ain; Rafiq, Naushaba; Tauseef, Saima [Biomedicine and Pharmacotherapy, 2022, vol. 146]
  • 2
  • [ 75-15-0 ]
  • [ 1673-47-8 ]
  • [ 41491-54-7 ]
YieldReaction ConditionsOperation in experiment
89% With potassium hydroxide In ethanol for 20h; Reflux;
76% With potassium hydroxide In ethanol for 14h; Reflux;
58% In N,N-dimethyl-formamide at 40 - 70℃; Inert atmosphere; 4.7 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 Heating;
With potassium hydroxide In ethanol for 8h; Heating;
With potassium hydroxide In ethanol
Stage #1: carbon disulfide; 3-chlorobenzhydrazide With potassium hydroxide In ethanol Reflux; Stage #2: With hydrogenchloride In ethanol; water
With potassium hydroxide In ethanol Reflux; General Procedure for the Synthesis of 5-Substituted Aryl/aralkyl-1,3,4-oxadiazol-2-thiols (4a-k) General procedure: The aryl/aralkyl acid hydrazides (0.01 mol, 3a-k) were dissolved in ethanol(35-40 mL) followed by the addition of KOH (0.03 mol) and CS2 (0.01 mol) in 250 mLround bottom flask fitted with a reflux condenser. The reaction mixture was refluxedfor 3-6 h along with proper stirring and the progress of reaction was monitored byTLC. After completion of reaction, the reaction mixture was diluted with distilled H2O(70-75 mL) and acidified with dilute HCl (pH 2-3) to convert salt of oxadiazole into acidicform. Precipitates of corresponding 5-substituted-1,3,4-oxadiazole-2-thiols (4a-k) werefiltered, washed with distilled water, and dried. To get the pure product, precipitates wererecrystallized from methanol.17-19
With potassium hydroxide In ethanol; water Reflux;
Stage #1: carbon disulfide; 3-chlorobenzhydrazide With potassium hydroxide In ethanol Stage #2: With hydrogenchloride In water
With potassium hydroxide In ethanol for 20h; Reflux;
With potassium hydroxide In ethanol Reflux; 2.4. Procedure for the synthesis of 5-substituted-1,3,4-oxadiazol-2-thiols (4a-o) General procedure: The aralkyl/aryl acid hydrazides (0.01 mol; 3a-o) were dissolved in 20 mLabsolute C2H5OH in a 250 mL of round bottom flask. Solid KOH (0.02 mol)and carbon disulphide (0.02 mol) were added to reaction flask. The reactioncontents were refluxed for 4-5 hrs with continuous stirring. H2S was evolvedduring the completion of reaction. Completion of reaction was confirmed bythin layer chromatography by using n-hexane and ethyl acetate (3:2) as mobilephase to develop a chromatogram. After confirmation, cold distilled water wasadded to the flask contents along with the addition of dilute HCl (pH 4-5).Precipitates of title compounds were filtered, washed with distilled waterand dried. To obtain the pure products, precipitates were recrystallized frommethanol.
Stage #1: carbon disulfide; 3-chlorobenzhydrazide With potassium hydroxide In ethanol Reflux; Stage #2: With hydrogenchloride
With hydrazine hydrate; potassium hydroxide In ethanol Reflux; General procedure for synthesis of 5-((un)substituted-phenyl)-1,3,4-oxadiazol-2-thiols (VIIa-n). General procedure: Solid KOH (0.03 mol) was dissolved in 25 mL EtOH on reflux in a 100 mL round-bottom flask. (Un)Substituted-benzohydrazide (VIa-n) (0.03 mol) was refluxed with CS2 (0.06 mol) in this basified EtOH for 5-6 h. The reaction was monitored by TLC. At completion, excess ice-cold distilled water (60 mL) wasadded to form homogeneous solution. pH was adjusted to 5-6 by pouring dilute HCl; precipitatethus formed was filtered, washed with distilled water and dried. The formed products (VIIa-n) were also re-crystallized from EtOH [18, 19].
Stage #1: carbon disulfide; 3-chlorobenzhydrazide With potassium hydroxide In ethanol at 80℃; Stage #2: With hydrogenchloride; water at 20℃;
Stage #1: carbon disulfide; 3-chlorobenzhydrazide 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: carbon disulfide; 3-chlorobenzhydrazide With sodium hydroxide Stage #2: With hydrogenchloride
With potassium hydroxide In ethanol for 6h; Reflux;
In N,N-dimethyl-formamide for 10h; Sonication; 4.2.1. general procedure for the synthesis of 2-mercapto-1,3,4-oxadiazolederivatives (compounds 85-110) General procedure: Carbon disulfide (50 mmol 4.7 mL) was added dropwise to the suspension including carboxyhydrazides (compound 59-84, 50 mmol) in DMF (5 mL) processed to an ultrasonic bath for 10 h. Hydrogen sulfide emission was treated with a saturated solution of sodium bicarbonate.The reaction mixture was added to 20 g crushed ice containing excess of salt. The solid phase was filtered with Buchner funnel, washed with water, and dried to obtain compound 85-110, respectively.
With potassium hydroxide In ethanol for 7h; Reflux;
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]Location in patent: experimental part Al-Janabi, Ahmed S.M.; Al-Soumadaiy; Khear-Allah, Bushra A. [Oriental Journal of Chemistry, 2011, vol. 27, # 4, p. 1465 - 1473]
[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]Chao, Shu-Jun; Hui, Xin-Ping; Li, Shuo; Qiu, Zao-Zao; Xu, Peng-Fei; Zhang, Zi-Yi; Wang, Qin; Guan, Zuo-Wu [Journal of the Chinese Chemical Society, 2005, vol. 52, # 3, p. 539 - 544]
[5]Li, Yan; Liu, Jie; Zhang, Hongquan; Yang, Xiangping; Liu, Zhaojie [Bioorganic and Medicinal Chemistry Letters, 2006, vol. 16, # 8, p. 2278 - 2282]
[6]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]
[7]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]
[8]Aziz-Ur-Rehman; Gul, Samreen; Abbasi, Muhammad Athar; Nafeesa, Khadija; Akhtar, Muhammad Nadeem; Ahmad, Irshad; Afzal, Saira [Phosphorus, Sulfur and Silicon and the Related Elements, 2015, vol. 190, # 7, p. 1045 - 1055]
[9]Parikh, Kalpesh; Joshi, Abhishek; Kshatriya, Rahulsingh; Joshi, Deepkumar [Pharmaceutical Chemistry Journal, 2015, vol. 49, # 8, p. 523 - 529]
[10]Chen, Ling; Wang, Peiyi; Li, Zhenxing; Zhou, Lei; Wu, Zhibing; Song, Baoan; Yang, Song [Chinese Journal of Chemistry, 2016, vol. 34, # 12, p. 1236 - 1244]
[11]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]
[12]Aziz-Ur-Rehman; Ahtzaz, Samreen; Abbasi, Muhammad Athar; Siddiqui, Sabahat Zahra; Rasool, Shahid; Ahmad, Irshad [Journal of the Chilean Chemical Society, 2017, vol. 62, # 1, p. 3370 - 3375]
[13]Aziz-ur-Rehman; Arif; Abbasi; Siddiqui; Rasool; Shah [Russian Journal of Bioorganic Chemistry, 2017, vol. 43, # 3, p. 328 - 339][Bioorg. Khim., 2017, vol. 43, # 3, p. 328 - 339,12]
[14]Abbasi; Ramzan; Aziz-ur-Rehman; Siddiqui; Shah; Hassan; Seo; Ashraf; Mirza; Ismail [Russian Journal of Bioorganic Chemistry, 2018, vol. 44, # 6, p. 801 - 811][Bioorg. Khim., 2018, vol. 44, # 6, p. 801 - 811,11]
[15]Tian, Kun; Li, Xiao-Qin; Zhang, Li; Gan, Yi-Yuan; Meng, Jiao; Wu, Shou-Qun; Wan, Jin-Lin; Xu, Yang; Cai, Chao-Ting; Ouyang, Gui-Ping; Wang, Zhen-Chao [Chemical Papers, 2019, vol. 73, # 1, p. 17 - 25]
[16]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]
[17]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]
[18]Yu, Gang; Chen, Shunhong; He, Feng; Luo, Dexia; Zhang, Yu; Wu, Jian [Turkish Journal of Chemistry, 2019, vol. 43, # 4, p. 1075 - 1085]
[19]El-Zahabi, Mohamed Ayman; Sakr, Helmy; El-Adl, Khaled.; Zayed, Mohamed; Abdelraheem, Adel S.; Eissa, Sally I.; Elkady, Hazem; Eissa, Ibrahim H. [Bioorganic Chemistry, 2020, vol. 104]
[20]Liu, Jie; Zhang, Guang-Yu; Zhang, Zhe; Li, Bo; Chai, Fei; Wang, Qi; Zhou, Zi-Dan; Xu, Ling-Ling; Wang, Shou-Kai; Jin, Zhen; Tang, You-Zhi [Bioorganic Chemistry, 2021, vol. 112]
[21]Cao, Xiao; Liu, Fang; Liu, Liwei; Liu, Tingting; Peng, Feng; Wang, Qifan; Xie, Chengwei; Xue, Wei; Yang, Jinsong [Journal of Agricultural and Food Chemistry, 2021, vol. 69, # 37, p. 11085 - 11094]
[22]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]
  • 4
  • [ 74367-78-5 ]
  • [ 41491-54-7 ]
  • 5-(3-chlorophenyl)-2-((3,5-dinitrobenzyl)sulfanyl)-1,3,4-oxadiazole [ No CAS ]
  • 5
  • [ 1128-76-3 ]
  • [ 41491-54-7 ]
Same Skeleton Products
Historical Records