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Chemical Structure| 7461-34-9
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Product Details of [ 7461-34-9 ]

CAS No. :7461-34-9 MDL No. :MFCD00018682
Formula : C14H12ClNO Boiling Point : -
Linear Structure Formula :- InChI Key :LSMWDKIFKGLNSW-UHFFFAOYSA-N
M.W : 245.70 Pubchem ID :346668
Synonyms :

Safety of [ 7461-34-9 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H317-H319 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 7461-34-9 ]

* 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 [ 7461-34-9 ]

[ 7461-34-9 ] Synthesis Path-Downstream   1~8

  • 1
  • [ 100-46-9 ]
  • [ 74-11-3 ]
  • [ 7461-34-9 ]
YieldReaction ConditionsOperation in experiment
99% With Bromotrichloromethane; 4-(diphenylphosphino)benzyltrimethylammonium bromide; triethylamine In tetrahydrofuran at 60℃; for 6h; Inert atmosphere; 4.3 Typical experimental procedure for amidation with IS-PPh3 General procedure: IS-PPh3 (746 mg, 1.8 mmol) was dried by a vacuum pump for 2 h at 70 °C. To a flask containing IS-PPh3 were added 4-methoxycarboxylic acid (152 mg, 1.0 mmol), BrCCl3 (357 mg, 1.8 mmol), benzylamine (129 mg, 1.2 mmol), triethylamine (0.14 mL, 1.0 mmol), and THF (4 mL). The obtained mixture was stirred for 6 h at 60 °C under Ar atmosphere. After the reaction, diethyl ether (10 mL) and aq HCl (1 M, 2 mL) were added at 0 °C and the obtained mixture was stirred for 15-30 min at room temperature. Then, the reaction mixture was poured into water (8 mL) and the obtained mixture was extracted with diethyl ether (10 mL×4). The combined organic layer was washed with water (10 mL) and brine (10 mL), and then dried over Na2SO4. After removal of the solvent under reduced pressure, N-benzyl-4-methoxybenzamide was obtained in 93% yield with 99% purity, as estimated by 1H NMR measurement. For cinnamic and aliphatic amides (entries 18-25 in Table 2) and indole-2-carboxamide (entry 16 in Table 2), the reaction mixture was poured into water (8 mL) and the obtained mixture was extracted with chloroform (10 mL×4). The combined organic layer was washed with water (10 mL) and brine (10 mL), and then dried over Na2SO4. After removal of the solvent under reduced pressure, N-benzylamide was obtained. or the recovery of IS-Ph3PO, NaCl (5.0 g) was added to the aqueous layer. The aqueous solution was extracted with CHCl3 (10 mL×5) and the combined organic layer was dried over NaSO4. After removal of the solvent, IS-Ph3PO containing a trace amount of IS-Ph3P was obtained in 95% yield.
99% With borane-ammonia complex In 5,5-dimethyl-1,3-cyclohexadiene for 6h; Reflux;
92% With nickel ferrite nanoparticle In neat (no solvent) for 0.166667h; Irradiation; Sealed tube;
90% Stage #1: para-chlorobenzoic acid With 1-chlorobenzotriazole; triphenylphosphine In dichloromethane for 0.25h; Stage #2: benzylamine With triethylamine In dichloromethane at 20℃; for 0.416667h; Typical Procedure for Conversions of Carboxylic Acids to Amides.N-benzylbenzamide (Table 3, Entry 1) General procedure: To a cold solution of PPh3 (0.327 g, 1.25 mmol) in CH2Cl2 (3 mL), freshly preparedNCBT (0.188 g, 1.25 mmol) was added with continuous stirring. Benzoic acid (0.122 g,1 mmol) was then added and stirring was continued for 15 min. Benzylamine (0.267 g,2.5 mmol) was added and the temperature was raised up to room temperature. The whitesuspension was neutralized by triethylamine (0.139 mL). Stirring was continued for 30 minat room temperature. The progress of the reaction was followed by TLC. Upon completionof the reaction, the concentrated residue was passed through a short silica-gel columnusing n-hexane-ethyl acetate (8:1) as eluent. N-Benzylbenzamide was obtained with 95%(0.201 g) yield after removing the solvent under reduced pressure.
90% With oxalyl dichloride; Triphenylphosphine oxide In acetonitrile at 20℃; for 0.5h;
89% With N-[3-(N,N-dimethylamino)-propyl]-N'-ethyl-carbodiimide hydrochloride In N,N-dimethyl-formamide Inert atmosphere;
88% With 4-methyl-morpholine; 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium toluene-4-sulfonate In dichloromethane at 90℃; for 0.166667h; Microwave irradiation;
84% With tetrakis(dimethylamino)diboron In toluene for 7h; Reflux;
82% With butyltin hydroxide oxide In toluene at 110℃; for 12h; Dean-Stark; General procedure for the synthesis of Amides General procedure: To a 250 mL three-necked reaction flask equipped with an agitator, Dean-Stark trap with a reflux condenser, temperature sensor, added 50 mL toluene, phenylacetic acid (2.5 g, 19.68 mmol), benzylamine (1.96 g, 19.68 mmol) and catalyst (0.82 g, 18 mol %). The mixture was stirred under gentle reflux at 110 °C in an oil bath. Water collected in the Dean-Stark trap, and the progress of the reaction was monitored by TLC. After consumption of starting materials, the reaction mixture was concentrated under reduced pressure to recovered 40 mL of toluene. The mixture was cooled to 20-25 °C to this added 100 mL hexane and stirred for 2 h. The precipitated solid was filtered. Solid containing product and the catalyst washed with 25 mL NaHCO3 (5%) solution, 25 mL of water and dried in an oven at 60 °C for 3 h. Dried solid extracted with acetone or methanol and filtered to separate the catalyst and filtrate containing amide was concentrated under reduced pressure to afford target amide, 2a as white solid, 4.01 gm, yield 97%. Similarly, the scalability of the reaction was assessed, phenylacetic acid 25 gm (183 mmol) with benzylamine 19.68 gm (183 mmol) and 18 mol % of n-butyl stannoic acid (6.9 g, 33 mmol) in 500 mL toluene after 3 h, maximum conversion of amide was observed, and the product was isolated by the procedure mentioned above to give 40.5 gm, yield 98%.
With 2-nitrophenyl thiocyanate; tributylphosphine In tetrahydrofuran
86 %Spectr. With tris(1,2-dioxyphenyl)cyclotriphosphazene In toluene at 128℃; for 16h; Inert atmosphere; Dean-Stark; Amides; General Procedure General procedure: An oven-dried 50 mL two-necked round-bottom flask was equippedwith a Teflon coated magnetic stirrer bar and connected to an azeotropiccondenser. To seal the apparatus, a balloon was connected tothe azeotropic condenser by a three-way stopcock; then, the atmospherewas replaced by N2 gas. Under a flow of N2, the flask wascharged with the CA (0.5 mmol, 1 equiv) and TAP-1 (11.48 mg, 5mol%). Then, the amine (0.5 mmol, 1 equiv) was added under N2 flow,followed by the solvent (dehydrated toluene or chlorobenzene; 7 mL).The reaction mixture was stirred under azeotropic reflux at 128 °C(133 °C in the case of chlorobenzene) for 16 h. Thereafter, the reaction flask was cooled to r.t., and the solvent was evaporated under reducedpressure using a rotary evaporator. The purification was performedby a three-step acid/base extraction. To this end, a separatory funnelwas charged with H2O and a DCM solution of the crude product mixture;after extraction, the organic layers (3 × 25 mL of DCM) were collectedand washed with sat. aq Na2CO3 (25 mL). The aqueous layerwas subsequently extracted with DCM (3 × 25 mL), and the organicphases were combined. The combined organic phases were washedwith aq HCl (1 M, 25 mL). The aqueous phase was extracted withDCM (3 × 25 mL). The combined organic layers were washed withbrine solution, dried over Na2SO4, and filtered. Finally the solvent ofthe filtrate was removed under reduced pressure.
81 %Spectr. With phenylsilane; FeH6Mo6O24(3-)*3H3N*7H2O*3H(1+) In toluene at 120℃; for 36h; Schlenk technique; Inert atmosphere;

Reference: [1]Kawagoe, Yuhsuke; Moriyama, Katsuhiko; Togo, Hideo [Tetrahedron, 2013, vol. 69, # 19, p. 3971 - 3977]
[2]Ramachandran, P. Veeraraghavan; Hamann, Henry J. [Organic Letters, 2021, vol. 23, # 8, p. 2938 - 2942]
[3]Houlding, Thomas K.; Tchabanenko, Kirill; Rahman, Md. Taifur; Rebrov, Evgeny V. [Organic and Biomolecular Chemistry, 2013, vol. 11, # 25, p. 4171 - 4177]
[4]Rouhi-Saadabad, Hamed; Akhlaghinia, Batool [Phosphorus, Sulfur and Silicon and the Related Elements, 2015, vol. 190, # 10, p. 1703 - 1714]
[5]Jiang, Lixue; Yu, Jing; Niu, Fanfan; Zhang, Derundong; Sun, Xiaoling [Heteroatom Chemistry, 2017, vol. 28, # 2]
[6]Bai, Shao-Tao; Bheeter, Charles B.; Reek, Joost N. H. [Angewandte Chemie - International Edition, 2019, vol. 58, # 37, p. 13039 - 13043][Angew. Chem., 2019, vol. 131, # 37, p. 13173 - 13177,5]
[7]Janczewski, Łukasz; Zieliński, Dariusz; Kolesińska, Beata [Open Chemistry, 2021, vol. 19, # 1, p. 265 - 280]
[8]Sawant, Dinesh N.; Bagal, Dattatraya B.; Ogawa, Saeko; Selvam, Kaliyamoorthy; Saito, Susumu [Organic Letters, 2018, vol. 20, # 15, p. 4397 - 4400]
[9]Potadar, Santoshkumar M.; Mali, Anil S.; Waghmode, Krishnakant T.; Chaturbhuj, Ganesh U. [Tetrahedron Letters, 2018, vol. 59, # 52, p. 4582 - 4586]
[10]Grieco,P.A. et al. [Journal of Organic Chemistry, 1979, vol. 44, p. 2945 - 2947]
[11]Movahed, Farzaneh Soleymani; Sawant, Dinesh N.; Bagal, Dattatraya B.; Saito, Susumu [Synthesis, 2020, vol. 52, # 21, p. 3253 - 3262]
[12]Shi, Da; Wang, Aiping; Wang, Jingjing; Xie, Ya; Yu, Han [Chemical Communications, 2022, vol. 58, # 8, p. 1127 - 1130]
  • 2
  • [ 104-88-1 ]
  • [ 100-46-9 ]
  • [ 7461-34-9 ]
YieldReaction ConditionsOperation in experiment
98% With 3-mesityl-4-methylthiazol-3-ium bis((trifluoromethyl)sulfonyl)imide; 1,8-diazabicyclo[5.4.0]undec-7-ene In N,N-dimethyl-formamide at 60℃; Flow reactor; Electrochemical reaction;
92% Stage #1: 4-chlorobenzaldehyde With tert.-butylhydroperoxide; 1,1,1,3',3',3'-hexafluoro-propanol; tetra-(n-butyl)ammonium iodide In benzene at 70℃; for 6h; Stage #2: benzylamine In benzene at 20℃; for 12h;
92% With tert.-butylhydroperoxide In 1,4-dioxane at 60℃; for 8h; Inert atmosphere;
88% With tert.-butylhydroperoxide; copper(l) iodide; sodium hydride; 1,3-bis(mesityl)imidazolium chloride In acetonitrile at 90℃; for 6h; Inert atmosphere; Schlenk technique; Amides 3a-y; General Procedure General procedure: An oven-dried Schlenk tube was charged with a solution of NHCprecursor 1a (10 mol%) and CuI (10 mol%) in CH3CN (3 mL)under N2. NaH (10 mol%) was added, and the resulting mixturewas stirred vigorously for about 20-30 min and then the appropriatealdehyde (2.5mmol) and amine (2.5mmol) were added tothe flask together with TBHP (3 equiv). The mixture wasrefluxed for 6 h in an oil bath then cooled to r.t., filtered througha Celite pad, and washed with H2O. The organic portion wasextracted with EtOAc, dried (Na2SO4), and purified by columnchromatography (silica gel, EtOAc-hexane).
87% With polystyrene divinyl benzene-supported bis(benzimidazolylmethyl)aminecopper(II) chloride In acetonitrile at 60℃; for 6h; 2.4. General procedure for direct amidation reaction General procedure: In a typical reaction 60 mg of Cu(PS-BBMA)Cl2 was taken in 5mL acetonitrile, benzaldehyde (1.0 mmol) and benzylamine (1.2mmol) were added to it. The mixture was stirred at 60 °C for 6 h(monitored by TLC). The catalyst was separated by filtration andthe solution was concentrated in vacuo. The resulting residuewas purified by column chromatography on silica gel with ethylacetate/petroleum ether (1:8) as elutant to afford the amide product(Scheme 2).
79% With dihydridotetrakis(triphenylphosphine)ruthenium; sodium hydride; acetonitrile; 1,3-di(propan-2-yl)-1H-imidazol-3-ium bromide In toluene for 24h; Inert atmosphere; Reflux;
70% With oxygen; sodium hydroxide In tetrahydrofuran; water at 0℃; for 23h;
62% With sodium hydrogen sulfate; [bis(acetoxy)iodo]benzene In neat (no solvent) at 20℃; for 2h; Milling;

  • 3
  • [ 619-56-7 ]
  • [ 100-51-6 ]
  • [ 7461-34-9 ]
YieldReaction ConditionsOperation in experiment
92% With bis[dichloro(pentamethylcyclopentadienyl)iridium(III)]; caesium carbonate In toluene at 130℃; for 12h; 21 N-benzyl-4-chlorobenzamide 4- chlorobenzonitrile (137mg, 1mmol), [(IPr) AuNTf] (17mg, 0.02mmol, 2mol%),tetrahydrofuran (0.5ml), H 2O (0.5ml) were successively added to the reaction flask25mlSchlenk. After the mixture was reacted at 130 °C at 12 hours, cooled to roomtemperature, the solvent was removed in vacuo under reduced pressure. The [Cp * IrCl 2]2After (8mg, 0.01mmol, 1mol%), benzyl alcohol (130mg, 1.2mmol), cesium carbonate (65mg,0.2equiv.) And toluene (1ml) was added to the reaction flask and the reaction mixturewas continued at 130°C at 12h cooled to room temperature. The solvent was removedrotary evaporation, then purified by column chromatography (developing solvent: ethylacetate / petroleum ether) to give pure title compound Yield: 92%.
92% With C23H24ClIrN3OS(1+)*F6P(1-); caesium carbonate In toluene at 120℃;
85% With potassium carbonate at 160℃; for 12h;
76% With bis[dichloro(pentamethylcyclopentadienyl)iridium(III)] In neat (no solvent) at 160℃; for 3h; Microwave irradiation; N-Alkylation of Amides with Alcohols; General Procedure General procedure: N-Alkylation of Amides with Alcohols; General ProcedureThe amide (100 mg, 1 equiv), alcohol (3 equiv) and (Cp*IrCl2)2 (2.5mol%) were added to a microwave reactor tube. The reaction mixturewas subjected to microwave irradiation at 160 °C for 3 h. The mixture was allowed to cool to r.t. and H2O (10 mL) was added. Themixture was extracted with EtOAc (3 × 10 mL). The combined organiclayers were dried (Na2SO4) and filtered. The solvent was removedunder reduced pressure and the residue was purified usingflash silica gel chromatography with CH2Cl2-MeOH (95:5) to furnishthe N-alkylamide (Tables 2 and 3).
25% With potassium phosphate; 1,10-Phenanthroline; nickel dibromide In toluene at 130℃; for 48h; Schlenk technique; Inert atmosphere;
199 mg With caesium carbonate In toluene at 130℃; for 12h; Inert atmosphere; Schlenk technique;
With bis[dichloro(pentamethylcyclopentadienyl)iridium(III)]; caesium carbonate In toluene at 130℃; for 12h;

  • 4
  • [ 7461-34-9 ]
  • [ 82082-51-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: water; zirconium(IV) chloride / toluene / 22 h / 110 °C / Inert atmosphere; sealed tube 2: para-xylene / 22 h / 150 °C / Inert atmosphere; sealed tube
  • 6
  • [ 873-76-7 ]
  • [ 100-46-9 ]
  • [ 7461-34-9 ]
YieldReaction ConditionsOperation in experiment
97% With C49H41N4O2P2RuS(1+)*NO3(1-); potassium <i>tert</i>-butylate In toluene at 120℃; for 12h; Green chemistry; Typical procedure for amidation of amines with alcohols General procedure: In a 25 cm3 round bottomed flask, 0.20 mol% of ruthenium(II) catalyst, 2 mmol of alcohol and amine substrates, 15 mol% of potassium tert-butoxide (KtBuO) were placed and dissolved in 2.0 cm3 of toluene. The reaction flask was kept at 120 °C for 12 h in an oil bath. Upon completion of reaction (monitored by TLC), the solvent was removed under vacuum and the resulting residue was purified by column chromatography on silica gel using ethylacetate/n-hexane. The amide products were dried overnight under vacuum. The resulting amides were identified by comparison of the 1H and 13C NMR data with those previously reported (ESI† )
96% With C53H41ClN4O3P2Ru; sodium hydride; acetonitrile In toluene at 120℃; for 12h; Inert atmosphere; 2.4. Typical procedure for amidation of amines with alcohols In a 25 mL round bottomed flask were placed 0.25 mol% of ruthenium(II) catalyst, 1 mmol of alcohol, 1 mmol of amine, 20 mol % of sodium hydride (NaH), 5 mol% CH3CN and 2.0 mL of toluene. The reaction flask was heated at 120 C for 12 h under argon atmosphere. Upon completion of the reaction (reaction was monitored by TLC), the solvent was removed under vacuum and the resulting residue was purified by column chromatography on silica gel using ethyl acetate/n-hexane solvent mixture. The amide product was dried under vacuum overnight. The resulting amides were identified by comparison of the 1H and 13C NMR data with those previously reported (ESI).
92% With oxygen; sodium hydroxide In tetrahydrofuran; water at 25℃; for 12h; Green chemistry;
82% With [RuCl(p-cymene)(1,3-dibenzylbenzimidazolin-2-ylidene)(PPh3)]PF6; sodium hydride In toluene at 125℃; for 24h; chemoselective reaction;
75% With oxygen; sodium hydroxide In tetrahydrofuran; water at 35℃; for 24h;
75% With [RhCl2(p-cymene)]2; 1-ethyl-3-methyl-1H-benzo[d]imidazol-3-ium iodide; sodium hydride In toluene; mineral oil for 36h; Schlenk technique; Inert atmosphere; Reflux;
72% With [ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2; 1,3-dimethylbenzimidazolium Iodide; sodium hydride In toluene at 110℃; for 48h; Schlenk technique; Glovebox; Inert atmosphere; Reflux;
33% With 3-methyl-butan-2-one; [ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2; caesium carbonate; 1,4-di(diphenylphosphino)-butane In <i>tert</i>-butyl alcohol at 125℃; for 24h; Schlenk technique; Inert atmosphere; Representative Procedure for Formation of Amides from Alcohols General procedure: To an oven-dried, nitrogen purged Schlenk tube containing [Ru(p-cymene)Cl2]2(46.9 mg, 0.075 mmol), dppb (64.0 mg, 0.15 mmol) and Cs2CO3(97.7 mg, 0.30 mmol) was added alcohol (3 mmol), amine (0.33 mmol),3-methyl-2-butanone (0.8 ml, 7.5 mmol) and tBuOH(3 ml) and the reaction heated at reflux for 24 h. On completion, the reaction was allowed to cool to room temperature before the solvent was removed invacuo. The crude product was purified by column chromatography (diethyl ether/petroleum ether (b.p. 40-60 °C) as eluent) before recyrstallization from(dichloromethane/hexane), to afford the corresponding amide in good yield.

  • 7
  • [ 623-03-0 ]
  • [ 140-11-4 ]
  • [ 7461-34-9 ]
YieldReaction ConditionsOperation in experiment
82% With silica sulfuric acid at 100℃; for 1.5h; Green chemistry; General Procedure for the Preparation of N-Benzylamides in the Presence of Silica Sulfuric Acid General procedure: In the 10 mL round-bottomed flask, a mixture of the nitrile (1 mmol) and benzyl acetate (0.150 g, 1 mmol) in the presence of silica sulfuric acid (0.06 g, equal to 0.2 mmol H+)was heated in an oil bath at 100°C, with stirring. The progress of the reaction was monitored by TLC using methanol:n-hexane (1:10) as eluent. After completion of the reaction, the solid mixture was cooled and diluted with ethanol and filtered. The filtrate was evaporated to dryness and the residue was purified by column chromatography to give the pure products in 70-92% yields based on the starting nitrile.
  • 8
  • [ 100-46-9 ]
  • [ 1889-71-0 ]
  • [ 7461-34-9 ]
  • [ 1485-70-7 ]
YieldReaction ConditionsOperation in experiment
With oxygen; N,N,N,N-tetraethylammonium tetrafluoroborate; In N,N-dimethyl-formamide; at 25℃; for 12h;Electrolysis; General procedure: Constant current electrolyses were performed at 25C, using an Amel Model 552 potentiostat equipped with an Amel Model 731 integrator. All the experiments were carried out in a divided glass cell separated through a porous glass plug filled up with a layer of gel (i.e., methyl cellulose 0.5% vol dissolved in DMF-Et4NBF4 1.0moldm-3); Pt spirals (apparent area 0.8cm2) were used as both cathode and anode. DMF-Et4NBF4 0.1moldm-3 was used as solvent-supporting electrolyte system (catholyte: 10cm3; anolyte: 5cm3). The current density was 20mAcm-2. In the catholyte 0.5mmol of benzoin (or deoxybenzoin, or benzil) and 1.0mmol of amine were present, with continuous O2 bubbling. The electrolysis was stopped after a prefixed charge (see Tables 1-4), the oxygen bubbling was stopped and the catholyte was kept under stirring at rT for 12hours. Usual workup gave the benzamides reported in Tables 1-4. All the isolated benzamides gave spectral data identical to those reported in the literature. Products spectral characterisation is reported in the Supporting Information.
Same Skeleton Products
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