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[ CAS No. 84587-80-4 ] {[proInfo.proName]}

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Product Details of [ 84587-80-4 ]

CAS No. :84587-80-4 MDL No. :MFCD01341598
Formula : C9H8ClN3O Boiling Point : -
Linear Structure Formula :- InChI Key :ZBCXNGGSMCVRHL-UHFFFAOYSA-N
M.W : 209.63 Pubchem ID :583767
Synonyms :

Safety of [ 84587-80-4 ]

Signal Word:Danger Class:8
Precautionary Statements:P261-P264-P271-P280-P302+P352-P304+P340+P312-P305+P351+P338-P310-P332+P313-P362-P403+P233-P405-P501 UN#:1759
Hazard Statements:H315-H318-H335 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 84587-80-4 ]

* 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 [ 84587-80-4 ]

[ 84587-80-4 ] Synthesis Path-Downstream   1~51

  • 1
  • [ 934-32-7 ]
  • [ 79-04-9 ]
  • [ 84587-80-4 ]
YieldReaction ConditionsOperation in experiment
85% In benzene at 0 - 5℃; for 4h; Reflux;
75% With triethylamine In tetrahydrofuran for 12h; Ambient temperature;
65% In acetone at 0℃; Reflux;
63% Stage #1: 1H-benzimidazol-2-amine With potassium carbonate In acetone for 0.0833333h; Cooling with ice; Stage #2: chloroacetyl chloride In acetone at 0 - 5℃; for 6h; Reflux;
57.1% Stage #1: 1H-benzimidazol-2-amine With triethylamine In tetrahydrofuran at 0℃; for 0.75h; Stage #2: chloroacetyl chloride In tetrahydrofuran at 0℃; for 2h; General procedure for the synthesis of N-(1H-benzo[d]imidazol-2-yl)-2-chloroacetamide A solution of 2-aminobenzimidazole (0.5 g, 3.75 mmol) and triethylamine(0.52 mL, 3.75 mmol) in anhydrous tetrahydrofuran(THF) was stirred for 45 min. Subsequently, a solution of chloroacetylchloride (0.3 mL, 3.75 mmol) in THF was added drop wiseto the reaction mixture under ice cold conditions using a droppingfunnel and the contents were stirred further for 2 h. Completion ofthe reaction was monitored by TLC. The slurry was filtered and thefiltrate was evaporated under reduced pressure to obtain a solidresidue which was recrystallized from ethanol to afford 7 (0.45 g,57.17%), m.p. 198-200 C.43
51% Stage #1: 1H-benzimidazol-2-amine With triethylamine In tetrahydrofuran for 0.75h; Inert atmosphere; Stage #2: chloroacetyl chloride In tetrahydrofuran for 2h; Cooling with ice; Inert atmosphere;
With sodium hydroxide
With potassium carbonate In chloroform for 6h; Reflux; General Procedure for the Synthesis of 6a A mixture of 2a (0.1 mole), chloroacetyl chloride (0.1mole) and K2CO3 was refluxed in chloroform (20 ml) for aperiod of 6 h. Excess of solvent was removed under vacuum and residue was stirred with water (50 ml). The residue was washed with 5% NaHCO3 and subsequently with water. The crude product is dried and crystallized from methanol to furnish pale brown solid, which was then purified through column chromatography.
Alkaline conditions;
With triethylamine In tetrahydrofuran at 20℃; for 2h; 2.1.1. General Procedure for the Synthesis of the Compounds N-(1H-benzimidazol-2-yl)-2-mercaptoacetamide (1) 1H-Benzimidazol-2-amine (0.04 mol, 5.33 g) and triethylamine (0.048 mol, 6.70 mL) were dissolved in THF with a constant stirring at 0-5°C, then chloroacetyl chloride (0.048 mol, 3.82 mL) was added dropwise gradually to this solution. The reaction mixture thus obtained was further agitated for 2 h at room temperature. After the solvent was vaporised to dryness, the solid was filtered and washed with water. After that, raw product was recrystallised from ethanol.
With pyridine In dichloromethane at 0 - 20℃; for 12h;

Reference: [1]Location in patent: experimental part Mobinikhaledi, Akbar; Kalhor, Mehdi; Hatami, Masoome [Heterocyclic Communications, 2010, vol. 16, # 2-3, p. 165 - 170]
[2]Caroti; Ceccotti; Da Settimo; Primofiore; Franzone; Reboani; Cravanzola [Il Farmaco, 1989, vol. 44, # 3, p. 227 - 255]
[3]Location in patent: experimental part Mobinikhaledi, Akbar; Foroughifar, Naser; Kalhor, Mehdi; Mirabolfathy, Mansoureh [Journal of Heterocyclic Chemistry, 2010, vol. 47, # 1, p. 77 - 80]
[4]Yang, Shao-Kang; Kang, Joon S.; Oelschlaeger, Peter; Yang, Ke-Wu [ACS Medicinal Chemistry Letters, 2015, vol. 6, # 4, p. 455 - 460]
[5]Abbhi, Vasudha; Saini, Lovneet; Mishra, Srishti; Sethi, Gautam; Prem Kumar, Alan; Piplani, Poonam [Bioorganic and Medicinal Chemistry, 2017, vol. 25, # 21, p. 6071 - 6085]
[6]Li, Xue-Dong; Liu, Li; Cheng, Liang [Organic and Biomolecular Chemistry, 2018, vol. 16, # 47, p. 9191 - 9196]
[7]Ridi; Checchi [Annali di Chimica, 1954, vol. 44, p. 28,35]
[8]Ghate, Manjunath; Devi, Praveena; Parikh, Jignesh; Vyas, Vivek K. [Medicinal Chemistry, 2013, vol. 9, # 3, p. 474 - 485]
[9]Xiang, Yang; Chang, Ya-Nan; Ge, Ying; Kang, Joon S.; Zhang, Yi-Lin; Liu, Xiao-Long; Oelschlaeger, Peter; Yang, Ke-Wu [Bioorganic and Medicinal Chemistry Letters, 2017, vol. 27, # 23, p. 5225 - 5229]
[10]Evren, Asaf Evrim; Tekinkoca, Sinem; Yurttaş, Leyla [Letters in drug design and discovery, 2018, vol. 15, # 2, p. 154 - 159]
[11]Srinivasarao, Singireddi; Nandikolla, Adinarayana; Nizalapur, Shashidhar; Yu, Tsz Tin; Pulya, Sravani; Ghosh, Balaram; Murugesan, Sankaranarayanan; Kumar, Naresh; Chandra Sekhar, Kondapalli Venkata Gowri [RSC Advances, 2019, vol. 9, # 50, p. 29273 - 29292]
  • 4
  • [ 110-85-0 ]
  • [ 84587-80-4 ]
  • [ 84587-78-0 ]
YieldReaction ConditionsOperation in experiment
75% In ethanol Heating;
  • 5
  • [ 504-24-5 ]
  • [ 84587-80-4 ]
  • N-(1H-Benzoimidazol-2-yl)-2-(pyridin-4-ylamino)-acetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
76% In ethanol Heating;
  • 6
  • [ 591-55-9 ]
  • [ 84587-80-4 ]
  • N-(1H-Benzoimidazol-2-yl)-2-(pyrimidin-5-ylamino)-acetamide [ No CAS ]
  • 7
  • [ 84587-80-4 ]
  • [ 124-40-3 ]
  • [ 84587-73-5 ]
YieldReaction ConditionsOperation in experiment
75% In ethanol for 6h; Heating;
  • 8
  • [ 84587-80-4 ]
  • [ 1209989-15-0 ]
YieldReaction ConditionsOperation in experiment
50% With potassium carbonate In acetone for 4h; Reflux;
  • 9
  • [ 107-10-8 ]
  • [ 84587-80-4 ]
  • [ 1286735-18-9 ]
YieldReaction ConditionsOperation in experiment
56% Stage #1: propylamine With sulfur In N,N-dimethyl-formamide at 20℃; for 1h; Stage #2: N-(1H-benzo[d]imidazol-2-yl)-2-chloroacetamide In N,N-dimethyl-formamide at 20℃;
  • 10
  • [ 33966-50-6 ]
  • [ 84587-80-4 ]
  • [ 1286735-20-3 ]
YieldReaction ConditionsOperation in experiment
60% Stage #1: SEC-BUTYLAMINE With sulfur In N,N-dimethyl-formamide at 20℃; for 1h; Stage #2: N-(1H-benzo[d]imidazol-2-yl)-2-chloroacetamide In N,N-dimethyl-formamide at 20℃;
  • 11
  • [ 111-26-2 ]
  • [ 84587-80-4 ]
  • [ 1286735-22-5 ]
YieldReaction ConditionsOperation in experiment
61% Stage #1: hexan-1-amine With sulfur In N,N-dimethyl-formamide at 20℃; for 1h; Stage #2: N-(1H-benzo[d]imidazol-2-yl)-2-chloroacetamide In N,N-dimethyl-formamide at 20℃;
  • 12
  • [ 84587-80-4 ]
  • [ 578-54-1 ]
  • [ 1286735-28-1 ]
YieldReaction ConditionsOperation in experiment
60% Stage #1: ortho-ethylaniline With sulfur In N,N-dimethyl-formamide at 20℃; for 1h; Stage #2: N-(1H-benzo[d]imidazol-2-yl)-2-chloroacetamide In N,N-dimethyl-formamide at 20℃;
  • 13
  • [ 84587-80-4 ]
  • [ 2038-57-5 ]
  • [ 1286735-25-8 ]
YieldReaction ConditionsOperation in experiment
51% Stage #1: 3-Phenylpropan-1-amine With sulfur In N,N-dimethyl-formamide at 20℃; for 1h; Stage #2: N-(1H-benzo[d]imidazol-2-yl)-2-chloroacetamide In N,N-dimethyl-formamide at 20℃;
  • 14
  • [ 84587-80-4 ]
  • [ 108-91-8 ]
  • [ 1286735-24-7 ]
YieldReaction ConditionsOperation in experiment
57% Stage #1: cyclohexylamine With sulfur In N,N-dimethyl-formamide at 20℃; for 1h; Stage #2: N-(1H-benzo[d]imidazol-2-yl)-2-chloroacetamide In N,N-dimethyl-formamide at 20℃;
  • 15
  • [ 84587-80-4 ]
  • [ 110-58-7 ]
  • [ 1286735-21-4 ]
YieldReaction ConditionsOperation in experiment
72% Stage #1: n-Pentylamine With sulfur In N,N-dimethyl-formamide at 20℃; for 1h; Stage #2: N-(1H-benzo[d]imidazol-2-yl)-2-chloroacetamide In N,N-dimethyl-formamide at 20℃;
  • 16
  • [ 84587-80-4 ]
  • [ 109-73-9 ]
  • [ 1286735-19-0 ]
YieldReaction ConditionsOperation in experiment
53% Stage #1: N-butylamine With sulfur In N,N-dimethyl-formamide at 20℃; for 1h; Stage #2: N-(1H-benzo[d]imidazol-2-yl)-2-chloroacetamide In N,N-dimethyl-formamide at 20℃;
  • 17
  • [ 84587-80-4 ]
  • [ 62-53-3 ]
  • [ 1286735-27-0 ]
YieldReaction ConditionsOperation in experiment
53% Stage #1: aniline With sulfur In N,N-dimethyl-formamide at 20℃; for 1h; Stage #2: N-(1H-benzo[d]imidazol-2-yl)-2-chloroacetamide In N,N-dimethyl-formamide at 20℃;
  • 18
  • [ 84587-80-4 ]
  • [ 95-51-2 ]
  • [ 1286735-30-5 ]
YieldReaction ConditionsOperation in experiment
50% Stage #1: o-chloroaniline With sulfur In N,N-dimethyl-formamide at 20℃; for 1h; Stage #2: N-(1H-benzo[d]imidazol-2-yl)-2-chloroacetamide In N,N-dimethyl-formamide at 20℃;
  • 19
  • [ 84587-80-4 ]
  • [ 1003-03-8 ]
  • [ 1286735-23-6 ]
YieldReaction ConditionsOperation in experiment
60% Stage #1: Cyclopentamine With sulfur In N,N-dimethyl-formamide at 20℃; for 1h; Stage #2: N-(1H-benzo[d]imidazol-2-yl)-2-chloroacetamide In N,N-dimethyl-formamide at 20℃;
  • 20
  • [ 84587-80-4 ]
  • [ 88-05-1 ]
  • [ 1286735-31-6 ]
YieldReaction ConditionsOperation in experiment
50% Stage #1: 2,4,6-trimethylaniline With sulfur In N,N-dimethyl-formamide at 20℃; for 1h; Stage #2: N-(1H-benzo[d]imidazol-2-yl)-2-chloroacetamide In N,N-dimethyl-formamide at 20℃;
  • 21
  • [ 84587-80-4 ]
  • [ 100-46-9 ]
  • [ 1286735-26-9 ]
YieldReaction ConditionsOperation in experiment
58% Stage #1: benzylamine With sulfur In N,N-dimethyl-formamide at 20℃; for 1h; Stage #2: N-(1H-benzo[d]imidazol-2-yl)-2-chloroacetamide In N,N-dimethyl-formamide at 20℃;
  • 22
  • [ 84587-80-4 ]
  • [ 589-16-2 ]
  • [ 1286735-29-2 ]
YieldReaction ConditionsOperation in experiment
55% Stage #1: 4-aminoethylbenzene With sulfur In N,N-dimethyl-formamide at 20℃; for 1h; Stage #2: N-(1H-benzo[d]imidazol-2-yl)-2-chloroacetamide In N,N-dimethyl-formamide at 20℃;
  • 23
  • [ 84587-80-4 ]
  • [ 333-20-0 ]
  • C10H8N4OS [ No CAS ]
YieldReaction ConditionsOperation in experiment
In acetone for 12h; Reflux; General Procedure for the Synthesis of 7a A mixture of 6a (0.01 mole), KSCN (0.02 mole) and dry acetone (50 ml) was refluxed for 12 h. Excess of solvent wasremoved under vacuum and the residue was stirred withwater (50 ml). The solid product was filtered, washed withwater and dried. The crude product was crystallized frommethanol to furnish greenish solid.
  • 24
  • [ 95-54-5 ]
  • [ 84587-80-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: acetonitrile; water; methanol / 12 h / 20 °C 2: potassium carbonate / chloroform / 6 h / Reflux
Multi-step reaction with 2 steps 1.1: water / 48 h / 20 °C / Cooling with ice 2.1: triethylamine / tetrahydrofuran / 0.75 h / 0 °C 2.2: 2 h / 0 °C
Multi-step reaction with 2 steps 1: methanol / 0.08 h / Reflux 2: pyridine / dichloromethane / 12 h / 0 - 20 °C
  • 25
  • [ 84587-80-4 ]
  • [ 1353654-28-0 ]
  • 4-(5-((2-((1H-benzo[d]imidazol-2-yl)amino)-2-oxoethyl)thio)-4H-1,2,4-triazol-3-yl)butanoic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
60% Stage #1: 4-(5-mercapto-4H-1,2,4-triazol-3-yl)butanoic acid With sodium hydroxide In ethanol for 0.0833333h; Stage #2: N-(1H-benzo[d]imidazol-2-yl)-2-chloroacetamide In ethanol for 6h; Reflux;
Alkaline conditions;
  • 26
  • [ 84587-80-4 ]
  • [ 1119452-21-9 ]
  • 2-(5-((2-((1H-benzo[d]imidazol-2-yl)amino)-2-oxoethyl)thio)-4H-1,2,4-triazol-3-yl)benzoic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
83% Stage #1: 2-(5-mercapto-4H-1,2,4-triazol-3-yl)benzoic acid With potassium carbonate In acetone for 0.0833333h; Stage #2: N-(1H-benzo[d]imidazol-2-yl)-2-chloroacetamide In acetone for 6h; Reflux;
Alkaline conditions;
  • 27
  • 3-(5-mercapto-4H-1,2,4-triazol-3-yl)propanoic acid [ No CAS ]
  • [ 84587-80-4 ]
  • 3-(5-((2-((1H-benzo[d]imidazol-2-yl)amino)-2-oxoethyl)thio)-4H-1,2,4-triazol-3-yl)propanoic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
78% Stage #1: 3-(5-mercapto-4H-1,2,4-triazol-3-yl)propanoic acid With sodium hydroxide In ethanol for 0.0833333h; Stage #2: N-(1H-benzo[d]imidazol-2-yl)-2-chloroacetamide In ethanol for 6h; Reflux;
Alkaline conditions;
  • 28
  • [ 84587-80-4 ]
  • [ 121-45-9 ]
  • dimethyl {2-[(1H-benzo[d]imidazol-2-yl)amino]-2-oxoethyl}phosphonate [ No CAS ]
YieldReaction ConditionsOperation in experiment
77% at 20 - 120℃; for 12h; Inert atmosphere; General procedure for the preparation of phosphate esters General procedure: Under the protection of N2, triethyl phosphate (0.012 mol) wasadded to the corresponding chloride (0.01 mol) at room temperature; the resulting mixture was refluxed at 120°Cfor12h,during which time the reaction was monitored by TLC (Rf =0.5, AcOEt/petroleumether 2:1). The cooled mixture was purified by flash chromatography (CHCl3/AcOEt 4:1) to yield thephosphonatesQ1, Q2,andQ3.
  • 29
  • [ 84587-80-4 ]
  • N-(1H-benzo[d]imidazol-2-yl)-2-iodoacetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
With sodium iodide In acetone at 60℃; for 0.5h; General procedure for the synthesis of acetamide derivatives 9a-m A solution of N-(1H-benzo[d]imidazol-2-yl)-2-chloracetamide(7) (1.91 mmol) and sodium iodide (1.90 mmol) in dry acetonewas refluxed with stirring at 60 C for 30 min.
With potassium iodide In acetone at 55℃; for 12h;
  • 30
  • 2‐(5‐mercapto‐1,3,4‐thiadiazol‐2‐yl)phenol [ No CAS ]
  • [ 84587-80-4 ]
  • N-(1H-benzimidazol-2-yl)-2-((5-(2-hydroxyphenyl)-1,3,4-thiadiazol-2-yl)thio)acetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
38% With potassium carbonate In acetone Reflux; 1.3.1 General procedure 1 General procedure: To a solution of mercaptoazoles (1.0 mmol) dissolved in 25 mL acetone was added N-benzimidazolyl-2-chloroacetamide or nitro substituted benzimidazol (1.0 mmol) in acetone and K2CO3 (0.14 g, 1.0 mmol), refluxed for 6-12 h, and then cooled to room temperature. The reaction mixture was slowly poured into 10 mL of cold water. The resulting solid was collected, washed with water, acetone and recrystallization with EtOH, and the crystals were dried to give the azolylthioacetamides 1, 2 and 23.
  • 31
  • [ 84587-80-4 ]
  • [ 29638-33-3 ]
  • N-(1H-benzo[d]imidazol-2-yl)-2-((5-(2-hydroxyphenyl)-1,3,4-oxadiazol-2-yl)thio)acetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
46% With potassium carbonate In acetone Reflux; 1.3.1 General procedure 1 General procedure: To a solution of mercaptoazoles (1.0 mmol) dissolved in 25 mL acetone was added N-benzimidazolyl-2-chloroacetamide or nitro substituted benzimidazol (1.0 mmol) in acetone and K2CO3 (0.14 g, 1.0 mmol), refluxed for 6-12 h, and then cooled to room temperature. The reaction mixture was slowly poured into 10 mL of cold water. The resulting solid was collected, washed with water, acetone and recrystallization with EtOH, and the crystals were dried to give the azolylthioacetamides 1, 2 and 23.
  • 32
  • [ 84587-80-4 ]
  • [ 29546-25-6 ]
  • N-(1H-benzimidazol-2-yl)-2-((5-benzyl-1,3,4-thiadiazol-2-yl)thio)acetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
32% With potassium hydroxide In ethanol for 6h; Reflux; 1.3.2 General procedure 2 General procedure: To a solution of potassium hydroxide (0.057 g, 1.2mmol) and mercaptoazoles (1.0 mmol) dissolved in 10 mL of ethanol was added N-benzimidazolyl-2-chloroacetamide, N-benzoxazolyl-2-chloroacetamide or nitro substituted benzimidazolyl-2-chloroacetamide (1.0 mmol) and refluxed for 6 h, the solvent was removed under reduced pressure, the resulting residue was poured into 5 mL of saturated NaHCO3 solution and stayed overnight. The solid was collected by filtration and boiled with hot MeOH, then the residues was filtrate and dried under vacuum to offer the azolylthioacetamides 3-16, 18-22 and 26-28.
  • 33
  • [ 84587-80-4 ]
  • [ 23288-90-6 ]
  • N-(1H-benzimidazol-2-yl)-2-((5-benzyl-1,3,4-oxadiazol-2-yl)thio)acetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
43% With potassium hydroxide In ethanol for 6h; Reflux; 1.3.2 General procedure 2 General procedure: To a solution of potassium hydroxide (0.057 g, 1.2mmol) and mercaptoazoles (1.0 mmol) dissolved in 10 mL of ethanol was added N-benzimidazolyl-2-chloroacetamide, N-benzoxazolyl-2-chloroacetamide or nitro substituted benzimidazolyl-2-chloroacetamide (1.0 mmol) and refluxed for 6 h, the solvent was removed under reduced pressure, the resulting residue was poured into 5 mL of saturated NaHCO3 solution and stayed overnight. The solid was collected by filtration and boiled with hot MeOH, then the residues was filtrate and dried under vacuum to offer the azolylthioacetamides 3-16, 18-22 and 26-28.
  • 34
  • [ 84587-80-4 ]
  • [ 13373-10-9 ]
  • 2-((4-amino-5-benzyl-4H-1,2,4-triazol-3-yl)thio)-N-(1H-benzimidazol-2-yl)acetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
54% With potassium hydroxide In ethanol for 6h; Reflux; 1.3.2 General procedure 2 General procedure: To a solution of potassium hydroxide (0.057 g, 1.2mmol) and mercaptoazoles (1.0 mmol) dissolved in 10 mL of ethanol was added N-benzimidazolyl-2-chloroacetamide, N-benzoxazolyl-2-chloroacetamide or nitro substituted benzimidazolyl-2-chloroacetamide (1.0 mmol) and refluxed for 6 h, the solvent was removed under reduced pressure, the resulting residue was poured into 5 mL of saturated NaHCO3 solution and stayed overnight. The solid was collected by filtration and boiled with hot MeOH, then the residues was filtrate and dried under vacuum to offer the azolylthioacetamides 3-16, 18-22 and 26-28.
  • 35
  • [ 84587-80-4 ]
  • [ 85103-36-2 ]
  • N-(1H-benzimidazol-2-yl)-2-((5-(3-nitrophenyl)-1,3,4-thiadiazol-2-yl)thio)acetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
32% With potassium hydroxide In ethanol for 6h; Reflux; 1.3.2 General procedure 2 General procedure: To a solution of potassium hydroxide (0.057 g, 1.2mmol) and mercaptoazoles (1.0 mmol) dissolved in 10 mL of ethanol was added N-benzimidazolyl-2-chloroacetamide, N-benzoxazolyl-2-chloroacetamide or nitro substituted benzimidazolyl-2-chloroacetamide (1.0 mmol) and refluxed for 6 h, the solvent was removed under reduced pressure, the resulting residue was poured into 5 mL of saturated NaHCO3 solution and stayed overnight. The solid was collected by filtration and boiled with hot MeOH, then the residues was filtrate and dried under vacuum to offer the azolylthioacetamides 3-16, 18-22 and 26-28.
  • 36
  • [ 84587-80-4 ]
  • [ 51805-88-0 ]
  • 2-((5-(2-aminophenyl)-1,3,4-thiadiazol-2-yl)thio)-N-(1H-benzimidazol-2-yl)acetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
45% With potassium hydroxide In ethanol for 6h; Reflux; 1.3.2 General procedure 2 General procedure: To a solution of potassium hydroxide (0.057 g, 1.2mmol) and mercaptoazoles (1.0 mmol) dissolved in 10 mL of ethanol was added N-benzimidazolyl-2-chloroacetamide, N-benzoxazolyl-2-chloroacetamide or nitro substituted benzimidazolyl-2-chloroacetamide (1.0 mmol) and refluxed for 6 h, the solvent was removed under reduced pressure, the resulting residue was poured into 5 mL of saturated NaHCO3 solution and stayed overnight. The solid was collected by filtration and boiled with hot MeOH, then the residues was filtrate and dried under vacuum to offer the azolylthioacetamides 3-16, 18-22 and 26-28.
  • 37
  • [ 84587-80-4 ]
  • [ 32058-76-7 ]
  • 2-((5-(2-aminophenyl)-1,3,4-oxadiazol-2-yl)thio)-N-(1H-benzimidazol-2-yl)acetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
28% With potassium hydroxide In ethanol for 6h; Reflux; 1.3.2 General procedure 2 General procedure: To a solution of potassium hydroxide (0.057 g, 1.2mmol) and mercaptoazoles (1.0 mmol) dissolved in 10 mL of ethanol was added N-benzimidazolyl-2-chloroacetamide, N-benzoxazolyl-2-chloroacetamide or nitro substituted benzimidazolyl-2-chloroacetamide (1.0 mmol) and refluxed for 6 h, the solvent was removed under reduced pressure, the resulting residue was poured into 5 mL of saturated NaHCO3 solution and stayed overnight. The solid was collected by filtration and boiled with hot MeOH, then the residues was filtrate and dried under vacuum to offer the azolylthioacetamides 3-16, 18-22 and 26-28.
  • 38
  • [ 84587-80-4 ]
  • [ 174574-09-5 ]
  • 2-((5-(2-aminophenyl)-4H-1,2,4-triazol-3-yl)thio)-N-(1H-benzimidazol-2-yl)acetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
63% With potassium hydroxide In ethanol for 6h; Reflux; 1.3.2 General procedure 2 General procedure: To a solution of potassium hydroxide (0.057 g, 1.2mmol) and mercaptoazoles (1.0 mmol) dissolved in 10 mL of ethanol was added N-benzimidazolyl-2-chloroacetamide, N-benzoxazolyl-2-chloroacetamide or nitro substituted benzimidazolyl-2-chloroacetamide (1.0 mmol) and refluxed for 6 h, the solvent was removed under reduced pressure, the resulting residue was poured into 5 mL of saturated NaHCO3 solution and stayed overnight. The solid was collected by filtration and boiled with hot MeOH, then the residues was filtrate and dried under vacuum to offer the azolylthioacetamides 3-16, 18-22 and 26-28.
  • 39
  • [ 84587-80-4 ]
  • [ 97035-89-7 ]
  • 2-((4-amino-5-(2-aminophenyl)-4H-1,2,4-triazol-3-yl)thio)-N-(1H-benzimidazol-2-yl)acetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
46% With potassium hydroxide In ethanol for 6h; Reflux; 1.3.2 General procedure 2 General procedure: To a solution of potassium hydroxide (0.057 g, 1.2mmol) and mercaptoazoles (1.0 mmol) dissolved in 10 mL of ethanol was added N-benzimidazolyl-2-chloroacetamide, N-benzoxazolyl-2-chloroacetamide or nitro substituted benzimidazolyl-2-chloroacetamide (1.0 mmol) and refluxed for 6 h, the solvent was removed under reduced pressure, the resulting residue was poured into 5 mL of saturated NaHCO3 solution and stayed overnight. The solid was collected by filtration and boiled with hot MeOH, then the residues was filtrate and dried under vacuum to offer the azolylthioacetamides 3-16, 18-22 and 26-28.
  • 40
  • [ 84587-80-4 ]
  • C7H8N4S2 [ No CAS ]
  • 2-((4-amino-5-(thiophen-2-ylmethyl)-4H-1,2,4-triazol-3-yl)thio)-N-(1H-benzo[d]imidazol-2-yl)acetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
37% With potassium hydroxide In ethanol for 6h; Reflux; 1.3.2 General procedure 2 General procedure: To a solution of potassium hydroxide (0.057 g, 1.2mmol) and mercaptoazoles (1.0 mmol) dissolved in 10 mL of ethanol was added N-benzimidazolyl-2-chloroacetamide, N-benzoxazolyl-2-chloroacetamide or nitro substituted benzimidazolyl-2-chloroacetamide (1.0 mmol) and refluxed for 6 h, the solvent was removed under reduced pressure, the resulting residue was poured into 5 mL of saturated NaHCO3 solution and stayed overnight. The solid was collected by filtration and boiled with hot MeOH, then the residues was filtrate and dried under vacuum to offer the azolylthioacetamides 3-16, 18-22 and 26-28.
  • 41
  • [ 84587-80-4 ]
  • [ 21528-04-1 ]
  • 2,2'-((5,5'-(ethane-1,2-diyl)bis(1,3,4-thiadiazole-5,2-diyl))bis(sulfanediyl))bis(N-(1H-benzimidazol-2-yl)acetamide) [ No CAS ]
YieldReaction ConditionsOperation in experiment
33% With potassium hydroxide In ethanol for 6h; Reflux; 1.3.2 General procedure 2 General procedure: To a solution of potassium hydroxide (0.057 g, 1.2mmol) and mercaptoazoles (1.0 mmol) dissolved in 10 mL of ethanol was added N-benzimidazolyl-2-chloroacetamide, N-benzoxazolyl-2-chloroacetamide or nitro substituted benzimidazolyl-2-chloroacetamide (1.0 mmol) and refluxed for 6 h, the solvent was removed under reduced pressure, the resulting residue was poured into 5 mL of saturated NaHCO3 solution and stayed overnight. The solid was collected by filtration and boiled with hot MeOH, then the residues was filtrate and dried under vacuum to offer the azolylthioacetamides 3-16, 18-22 and 26-28.
  • 42
  • [ 84587-80-4 ]
  • [ 13183-79-4 ]
  • N-(1H-benzimidazol-2-yl)-2-[(1-methyl-1H-tetrazol-5-yl)thio]acetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
76% With potassium carbonate In acetone for 6h; 2.1.2. N-(1H-benzimidazol-2-yl)-2-(substituted mercapto)acetamide derivatives (2a-2h) A mixture of N-(1H-benzimidazol-2-yl)-2-chloroacetamide(1) (2.39 mmol, 0.5 g), appropriate mercapto derivatives (3.20 mmol) and K2CO3 (2.39 mmol, 0.24 g) in acetone was stirred for 6 hours. At the end of the period, the solvent was vaporised and the residue was washed with water and filtered. After dryness, raw product was recrystallised from alcohol. Some chemical properties were given in Table 1. 2.1.3. N-(1H-benzimidazol-2-yl)-2-[(1-methyl-1H-tetrazol-5-yl)thio]acetamide (2a) m. p. 235°C, 1H-NMR (300 MHz, DMSO-d6, ppm) δ4.00 (s, 3H, CH3), 4.35 (s, 2H, CH2), 7.08-7.11 (m, 2H, Ar-H), 7.41-7.44 (m, 2H, Ar-H), 12.02 (brs, 2H, NH).13C-NMR (75 MHz, DMSO-d6, ppm) 34.17 (CH3), 37.75(CH2), 114.40, 121.81, 136.04, 153.73, 167.90 (C=O). MS[M+1]+: m/z 290.0819. For C11H11N7OS calculated: Elemental Analysis: % C45.67; %H 3.83; %N 33.89; found: %C 45.66; %H 3.84; %N33.87.
  • 43
  • [ 84587-80-4 ]
  • [ 24854-43-1 ]
  • N-(1H-benzimidazol-2-yl)-2-((4-methyl-4H-1,2,4-triazol-3-yl)thio)acetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
78% With potassium carbonate In acetone for 6h; 2.1.2. N-(1H-benzimidazol-2-yl)-2-(substituted mercapto)acetamide derivatives (2a-2h) A mixture of N-(1H-benzimidazol-2-yl)-2-chloroacetamide(1) (2.39 mmol, 0.5 g), appropriate mercapto derivatives (3.20 mmol) and K2CO3 (2.39 mmol, 0.24 g) in acetone was stirred for 6 hours. At the end of the period, the solvent was vaporised and the residue was washed with water and filtered. After dryness, raw product was recrystallised from alcohol. Some chemical properties were given in Table 1.
  • 44
  • [ 84587-80-4 ]
  • [ 149-30-4 ]
  • N-(1H-benzimidazol-2-yl)-2-(benzothiazol-2-ylthio)acetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
75% With potassium carbonate In acetone for 6h; 2.1.2. N-(1H-benzimidazol-2-yl)-2-(substituted mercapto)acetamide derivatives (2a-2h) A mixture of N-(1H-benzimidazol-2-yl)-2-chloroacetamide(1) (2.39 mmol, 0.5 g), appropriate mercapto derivatives (3.20 mmol) and K2CO3 (2.39 mmol, 0.24 g) in acetone was stirred for 6 hours. At the end of the period, the solvent was vaporised and the residue was washed with water and filtered. After dryness, raw product was recrystallised from alcohol. Some chemical properties were given in Table 1.
  • 45
  • [ 84587-80-4 ]
  • [ 134469-07-1 ]
  • 2-((1H-benzimidazol-2-yl)thio)-N-(1H-benzimidazol-2-yl)acetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
74% With potassium carbonate In acetone for 6h; 2.1.2. N-(1H-benzimidazol-2-yl)-2-(substituted mercapto)acetamide derivatives (2a-2h) A mixture of N-(1H-benzimidazol-2-yl)-2-chloroacetamide(1) (2.39 mmol, 0.5 g), appropriate mercapto derivatives (3.20 mmol) and K2CO3 (2.39 mmol, 0.24 g) in acetone was stirred for 6 hours. At the end of the period, the solvent was vaporised and the residue was washed with water and filtered. After dryness, raw product was recrystallised from alcohol. Some chemical properties were given in Table 1.
  • 46
  • [ 84587-80-4 ]
  • [ 51618-29-2 ]
  • N-(1H-benzimidazol-2-yl)-2-((6-chlorobenzothiazol-2-yl)thio)acetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
75% With potassium carbonate; In acetone; for 6h; A mixture of N-(1H-benzimidazol-2-yl)-2-chloroacetamide(1) (2.39 mmol, 0.5 g), appropriate mercapto derivatives (3.20 mmol) and K2CO3 (2.39 mmol, 0.24 g) in acetone was stirred for 6 hours. At the end of the period, the solvent was vaporised and the residue was washed with water and filtered. After dryness, raw product was recrystallised from alcohol. Some chemical properties were given in Table 1.
  • 47
  • [ 6325-91-3 ]
  • [ 84587-80-4 ]
  • N-(1H-benzimidazol-2-yl)-2-((5-nitro-1H-benzimidazol-2-yl)thio)acetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
79% With potassium carbonate In acetone for 6h; 2.1.2. N-(1H-benzimidazol-2-yl)-2-(substituted mercapto)acetamide derivatives (2a-2h) A mixture of N-(1H-benzimidazol-2-yl)-2-chloroacetamide(1) (2.39 mmol, 0.5 g), appropriate mercapto derivatives (3.20 mmol) and K2CO3 (2.39 mmol, 0.24 g) in acetone was stirred for 6 hours. At the end of the period, the solvent was vaporised and the residue was washed with water and filtered. After dryness, raw product was recrystallised from alcohol. Some chemical properties were given in Table 1.
  • 48
  • [ 84587-80-4 ]
  • [ 27231-36-3 ]
  • N-(1H-benzimidazol-2-yl)-2-((5-methyl-1H-benzimidazol-2-yl)thio)acetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
78% With potassium carbonate In acetone for 6h; 2.1.2. N-(1H-benzimidazol-2-yl)-2-(substituted mercapto)acetamide derivatives (2a-2h) A mixture of N-(1H-benzimidazol-2-yl)-2-chloroacetamide(1) (2.39 mmol, 0.5 g), appropriate mercapto derivatives (3.20 mmol) and K2CO3 (2.39 mmol, 0.24 g) in acetone was stirred for 6 hours. At the end of the period, the solvent was vaporised and the residue was washed with water and filtered. After dryness, raw product was recrystallised from alcohol. Some chemical properties were given in Table 1.
  • 49
  • [ 84587-80-4 ]
  • [ 37052-78-1 ]
  • N-(1H-benzimidazol-2-yl)-2-((5-methoxy-1H-benzimidazol-2-yl)thio)acetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
76% With potassium carbonate; In acetone; for 6h; A mixture of N-(1H-benzimidazol-2-yl)-2-chloroacetamide(1) (2.39 mmol, 0.5 g), appropriate mercapto derivatives (3.20 mmol) and K2CO3 (2.39 mmol, 0.24 g) in acetone was stirred for 6 hours. At the end of the period, the solvent was vaporised and the residue was washed with water and filtered. After dryness, raw product was recrystallised from alcohol. Some chemical properties were given in Table 1.
  • 50
  • [ 84587-80-4 ]
  • [ 3395-04-8 ]
  • C16H13N5OS [ No CAS ]
YieldReaction ConditionsOperation in experiment
45% With sodium ethanolate In ethanol for 24h; Inert atmosphere; Reflux;
  • 51
  • [ 84587-80-4 ]
  • C10H16N4OS*C2HF3O2 [ No CAS ]
  • 2-(4-((2-acetamidothiazol-5-yl)methyl)piperazin-1-yl)-N-(1H-benzo[d]imidazole-2-yl)acetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
104 mg With potassium carbonate In acetonitrile at 20℃; General procedure for the synthesis of compounds 7j, 15-44 (ProcedureD). General procedure: To a stirred suspension of intermediates 11 (1.2 equiv) andK2CO3 (2.4 equiv) in ACN was added intermediates 14 (1.0 equiv), thereaction mixture was stirred at room temperature overnight. Themixture was diluted with H2O and extracted with EtOAc, the EtOAclayer was dried over Na2SO4, filtered off, and concentrated in vacuo. Thecrude product was purified by flash column chromatography (DCM:MeOH) to obtain the desired compounds.
104 mg With potassium carbonate In acetonitrile at 20℃; General procedure for the synthesis of compounds 7j, 15-44 (ProcedureD). General procedure: To a stirred suspension of intermediates 11 (1.2 equiv) andK2CO3 (2.4 equiv) in ACN was added intermediates 14 (1.0 equiv), thereaction mixture was stirred at room temperature overnight. Themixture was diluted with H2O and extracted with EtOAc, the EtOAclayer was dried over Na2SO4, filtered off, and concentrated in vacuo. Thecrude product was purified by flash column chromatography (DCM:MeOH) to obtain the desired compounds.
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