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[ CAS No. 621-06-7 ] {[proInfo.proName]}

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Product Details of [ 621-06-7 ]

CAS No. :621-06-7 MDL No. :MFCD00086905
Formula : C14H13NO Boiling Point : -
Linear Structure Formula :- InChI Key :KYPIASPTMDEDQB-UHFFFAOYSA-N
M.W : 211.26 Pubchem ID :225533
Synonyms :

Calculated chemistry of [ 621-06-7 ]

Physicochemical Properties

Num. heavy atoms : 16
Num. arom. heavy atoms : 12
Fraction Csp3 : 0.07
Num. rotatable bonds : 4
Num. H-bond acceptors : 1.0
Num. H-bond donors : 1.0
Molar Refractivity : 65.24
TPSA : 29.1 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : No
CYP2D6 inhibitor : Yes
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.67 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.16
Log Po/w (XLOGP3) : 2.7
Log Po/w (WLOGP) : 2.68
Log Po/w (MLOGP) : 3.01
Log Po/w (SILICOS-IT) : 2.97
Consensus Log Po/w : 2.7

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.14
Solubility : 0.152 mg/ml ; 0.000721 mol/l
Class : Soluble
Log S (Ali) : -2.96
Solubility : 0.229 mg/ml ; 0.00109 mol/l
Class : Soluble
Log S (SILICOS-IT) : -5.33
Solubility : 0.000997 mg/ml ; 0.00000472 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.29

Safety of [ 621-06-7 ]

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

Application In Synthesis of [ 621-06-7 ]

* 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 [ 621-06-7 ]

[ 621-06-7 ] Synthesis Path-Downstream   1~92

  • 1
  • [ 952-06-7 ]
  • [ 621-06-7 ]
YieldReaction ConditionsOperation in experiment
92% With trimethylsilylphosphate In benzene for 18h; Ambient temperature;
87% With 10-methyl-9-phenylacridin-10-ium perchlorate In 1,2-dichloro-ethane at 20℃; for 5h; Irradiation; Sealed tube;
With pyridine; benzenesulfonyl chloride
With diethyl ether; phosphorus pentachloride
Multi-step reaction with 2 steps 1: Et3N / tetrahydrofuran / 1 h / Ambient temperature 2: 83 percent / SbCl5, AgSbF6 / acetonitrile / 3 h / Heating

  • 2
  • [ 621-06-7 ]
  • [ 6636-01-7 ]
YieldReaction ConditionsOperation in experiment
70% Stage #1: 2,N-diphenylacetamide With Lawessons reagent In toluene for 4h; Reflux; Stage #2: In ethanol; toluene for 2h; Reflux; Typical procedure for the synthesis of thioamide 2 (1 mmol scale) General procedure: A mixture of amide 1 (1.0 mmol) and Lawesson’s reagent(0.60 mmol) was refluxed in toluene (4 mL). The reactionprogress was monitored by TLC until full consumption of thestarting amide was observed. To the cooled mixture was addedEtOH (2 mL, excess) and the resulting mixture was heated atreflux for 2 h. Then, the volatiles were removed under reducedpressure. The residue was diluted with ethyl acetate followed byaqueous workup. The organic phase was dried over anhydrousMgSO4. The solvent was removed under reduced pressure. Thereside was purified by silica gel column chromatography usingpetroleum ether/ethyl acetate as the eluent to afford the desiredthioamide 2.
20% With n-butyllithium; tetraphosphorus decasulfide In tetrahydrofuran; hexane for 16h; Heating;
With toluene bei Siedetemperatur;
With Lawessons reagent

  • 3
  • [ 5110-77-0 ]
  • [ 621-06-7 ]
YieldReaction ConditionsOperation in experiment
51% With nickel In isopropyl alcohol for 20h; Heating;
With sodium amalgam; ethanol
  • 4
  • [ 103-81-1 ]
  • [ 62-53-3 ]
  • [ 621-06-7 ]
YieldReaction ConditionsOperation in experiment
87% With sulfated tungstate In toluene for 12h; Reflux; Green chemistry;
81% With 1-(3-sulfopropyl)pyridinium phosphotungstate In neat (no solvent) at 120℃; for 0.833333h; Microwave irradiation; 4.3.11. N-Phenyl-2-phenylacetamide (4a) General procedure: To a mixture of amide (2 mmol) and amine (2.6 mmol) ina 10 mL round bottomed ask was added [PyPS]3PW12O40 (140 mg, 0.04 mmol). The reaction mixture was stirred at the corresponding temperature under MW (700 W). The progress of the reaction was monitored by TLC. On completion, the mixture was diluted with ethyl acetate (20 mL) with stirring for 30 min. The insoluble catalyst was recovered by filtration or centrifugation. The filtrate was evaporated and the residue in almost pure form. Recrystallization or column chromatography could be used for further purication.
78% With copper diacetate In tert-Amyl alcohol at 140℃; for 16h; Inert atmosphere;
76% With water; boric acid at 150℃; for 16h;
74% With [bis(acetoxy)iodo]benzene In neat (no solvent) at 120℃; for 0.333333h; Microwave irradiation; Green chemistry;
12% With water; copper diacetate; pipecolic Acid at 100℃; for 18h;
at 150℃;

  • 5
  • [ 103-82-2 ]
  • [ 62-53-3 ]
  • [ 621-06-7 ]
YieldReaction ConditionsOperation in experiment
98% With Titania nano-particle at 110℃; for 0.5h;
98% With mesocellular siliceous foam-supported boronic acid catalyst In toluene at 120℃; for 23h; Sealed tube; Dean-Stark;
97% With Fe(3+)-K-10 montmorillonite clay In chloroform for 7h; Heating;
96% With triethylamine; betamethasone sodium phosphate In N,N-dimethyl-formamide for 0.333333h; Ambient temperature;
96% With sulphate-modified mesoporous carbon In toluene at 110℃; for 10h; 2.4. Catalytic Activity Studies of S-MWCNTand S-MC General procedure: The catalytic activity of S-MWCNT and S-MC catalystswere investigated in the synthesis of acetamide derivativesusing substituted aromatic amines (aniline, benzyl amine,para-chloro aniline and para-methoxy aniline) and aromaticacids (phenyl acetic acid, phenylthio acetic acid andIndole 3-acetic acid) in a liquid phase reaction. In a typicalprocedure of synthesis of acetamide derivatives, mixture ofaromatic acid and substituted aromatic amine in 1:1 molarratio was refluxed at 110 C using 50 mg of catalyst with10 mL of toluene as solvent in a 100 mL R B flask fittedwith water cooled condenser. After a definite periodof time, the reaction mixture was cooled to room temperatureand filtered to separate the solid catalyst. The productwas recovered from the filtrate using sodium bicarbonateand ethyl acetate. The separated acetamide derivativewas confirmed from TLC, MP, 1HNMR techniques. Furtheroptimization of the reaction conditions was made byusing different amounts of the catalysts, varying the temperature,duration of the reaction. The effect of differentsolvents in the synthesis of acetamide derivatives was alsochecked.
95% Stage #1: phenylacetic acid With ethanaminium,N-(difluoro-λ4-sulfanylidene)-N-ethyl-,tetrafluoroborate In ethyl acetate at 21℃; for 2h; Inert atmosphere; Stage #2: aniline In ethyl acetate at 21℃; for 1h; Inert atmosphere;
95% With carbon disulfide; dmap; aluminum oxide In acetonitrile at 200℃; for 0.45h; Flow reactor; Green chemistry;
95% With Methyltrimethoxysilan In toluene for 24h; Reflux; Inert atmosphere;
94% With triethylamine; Phenyl N-phenylphosphoramidochloridate In dichloromethane for 1h; Ambient temperature;
89% Stage #1: phenylacetic acid With iron(III) chloride; acetic acid In toluene at 50℃; Green chemistry; Stage #2: aniline In toluene at 70 - 75℃; for 6h; Green chemistry;
87% With (1-methyl-3-(3-sulfopropyl)-1H-imidazol-3-ium)3[PW12O403-] In neat (no solvent) at 100℃; for 0.133333h; Green chemistry; 4.4 General procedure for the synthesis of amides (Table 3) General procedure: To a mixture of amine (2 mmol) and carboxylic acid (6 mmol) in a 10 mL round bottomed flask was added [MIMPS]3PW12O40 (140 mg, 0.04 mmol). The reaction mixture was stirred at 100 °C. The progress of the reaction was monitored by TLC. On completion, the mixture was diluted with ethyl acetate (20 mL) with stirring for 30 min. The insoluble catalyst was recovered by filtration. The filtrate was washed with satd solution of NaHCO3 (5 mL×3), brine, and dried over anhyd Na2SO4. The solvent was evaporated and the residue in almost pure form. Recrystallization or column chromatography could be used for further purification.
86% Stage #1: phenylacetic acid With (E)-ethyl 2-cyano-2-(2-nitrophenylsulfonyloxyimino)acetate; N-ethyl-N,N-diisopropylamine In dichloromethane at 25℃; Stage #2: aniline In dichloromethane at 25℃;
85% With ZnO nanofluid at 110℃; for 2.5h; neat (no solvent);
85% Stage #1: phenylacetic acid With ethyl 2-(tert-butoxycarbonyloxyimino)-2-cyanoacetate; N-ethyl-N,N-diisopropylamine In ethyl acetate at 0 - 5℃; for 1h; Stage #2: aniline In ethyl acetate at 0 - 5℃; for 2h;
81% With triethylamine; fluoro-N,N,N',N'-tetramethylformamidinium hexafluorophosphate In N,N-dimethyl-formamide at 0 - 20℃; for 2.5h;
81% With activated K60 silica gel In toluene at 110℃; for 24h;
79% With 5percent wt mesoporous structured silica (Pluronic 123)-1,3,5-triisopropylbenzene as template expander In toluene at 110℃; for 24h;
78% With n-butylstannoic acid In 5,5-dimethyl-1,3-cyclohexadiene for 15h; Dean-Stark; Reflux; 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%.
76% With dmap; triethyl phosphite In pyridine at 100 - 110℃; for 12h;
75% Stage #1: phenylacetic acid With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In dichloromethane at 0℃; for 0.0833333h; Inert atmosphere; Stage #2: aniline In dichloromethane at 20℃; for 12h; Inert atmosphere; 4.1. General procedure A: synthesis of amides General procedure: To a solution of phenyl acetic acid (500 mg, 2.85 mmol) in DCM (10 mL), HOBt (3.4 mmol, 1.2 equiv.), EDC.HCl (3.4 mmol, 1.2 equiv.) and DIPEA (11.4 mmol, 4.0 equiv.) was added at 0 C, stirred for 5 min at the same temperature. Then aniline (2.85 mmol, 1.0 equiv.), was added to the mixture and stirred for 12 h at ambient temperature. The reaction mixture was diluted with dichloromethane (25 mL), washed with saturated aqueous NaHCO3 solution (5 mL), H2O (2 X 5 mL), saturated brine solution (5 mL) and an organic layer was dried over Na2SO4. The crude material obtained after removal of solvent was purified by column chromatography (silica gel 230-400 mesh, ethyl acetate - pet ether) to afford corresponding amides.
73% With isocyanate de chlorosulfonyle; triethylamine In dichloromethane 1.) 0 - 10 deg C, 3 h, 2.) room temp., 5 h;
72% With thiopyridyl-benzisothiazole 1,1-dioxide (BID-SPy); triethylamine In dichloromethane Heating;
72% With sulfated tungstate In toluene for 18h; Reflux;
63% With triethylamine; benzenesulfonyl chloride In acetone at 20 - 23℃; for 0.0833333h;
61% With phenylsilane In acetonitrile at 20℃; for 24h;
60% With tris(2,2,2-trifluoroethyl) borate In acetonitrile at 100℃; for 15h; Sealed tube;
52% at 150℃; for 0.5h; microwave irradiation;
50% With 4 A molecular sieve at 180℃; for 2h;
46% With diphenylsilane In acetonitrile at 80℃; for 16h; Inert atmosphere; Sealed tube; Green chemistry;
28% With 1-Methylpyrrolidine; diphenylsilane In acetonitrile at 100℃; for 0.333333h; Microwave irradiation; Green chemistry;
With trichlorophosphate
With N,N-bis[2-oxo-3-oxazolidinyl]phosphorodiamidic chloride; triethylamine CH2Cl2, 1.) 30 min, 2.) 2 h; Yield given. Multistep reaction;
With Escherichia coli penicillin acylase; potassium chloride In water at 24.84℃; Enzymatic reaction;
With benzotriazol-1-ol; N-isopropylethylamine; diisopropyl-carbodiimide In 2-methyltetrahydrofuran at 18℃; for 4h; Green chemistry;
With dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 6h; 2.1 (1) The synthesis of N,2-diphenylacetamide (5a) [0226] After dissolving compound 2 (1.00 g, 7.34 mmol) in MC (30 ml), the activation for 30 minutes was carried out by the addition of DCC (1.82 g, 8.81 mmol). After the sufficient activation, aniline (0.75 g, 8.07 mmol) was added thereto and the agitation for 6 hours was carried out at room temperature. After the identification of the reaction progress with TLC, DCU was removed by the filtration and solvents were removed by the distillation under the reduced pressure. Then, the next reaction was followed without the purification process.
With magnesium(II) nitrate hexahydrate In octane at 120℃; for 24h;

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  • 6
  • [ 62-53-3 ]
  • [ 103-80-0 ]
  • [ 621-06-7 ]
YieldReaction ConditionsOperation in experiment
99% With samarium In acetonitrile at 20℃; for 3h;
95% In dichloromethane at 20℃; for 1h; Preparation of N, 2-diphenylacetamide (1a). To a solution of aniline (1.39 g, 15 mmol) in CH2Cl2 (25 mL), phenylacetyl chloride (1.3 mL, 10mmol) was added. The mixture was stirred at room temperature for 1 h. After that, HCl (1 N, 10mL) was added carefully and the solution was extracted with ethyl acetate (3x30 mL). The combined extracts was washed with saturated NaHCO3 (2x10 mL) and dried over Na2SO4. After removal of solvent, the residue was purified by recrystallization in EA to afford 1a (1.98 g, 95%)as a white solid. m.p. 116-117 °C. IR (KBr): 3461, 3284, 3254, 1658, 1601, 1439 cm-1. 1H NMR (500 MHz, CDCl3): δ 7.59 (s, 1H), 7.50 (d, J = 7.5 Hz, 2H), 7.40-7.37 (m, 2H), 7.34-7.32 (m,3H), 7.29-7.25 (m, 2H), 7.11-7.07 (m, 1H), 3.70 (s, 2H). 13C NMR (125 MHz, CDCl3): δ 169.49,137.81, 134.63, 129.57, 129.21, 129.00, 127.65, 124.53, 120.06, 44.77.
92% Stage #1: aniline With triethylamine In dichloromethane for 0.166667h; Cooling with ice; Stage #2: phenylacetyl chloride In dichloromethane for 3h; Cooling with ice; General procedure for the synthesis of 34a-36a, 39a-40a General procedure: To a round bottom flask was added DCM (10 mL), aniline (10 mmol) and triethylamine (15 mmol). The solution was stirred in ice bath for 10 min. Then, the acyl chloride (10 mmol) in DCM (10 mL) was added dropwise within 10 min. The resulted suspension was stirred for another 3 h. After completion of the reaction (monitored by TLC), the mixture was diluted with DCM (10 mL), and washed with saturated aqueous sodium carbonate (3×10 mL) and water (2×10 mL). The organic layer was washed with saturated brine and dried with anhydrous Na2SO4. The solvent was removed under reduced pressure to produce the crude product. Then, the recrystallization was conducted using EtOH to obtain the pure product.
90% With triethylamine In benzene for 6h; Heating;
85% With zinc powder In toluene for 0.583333h; Ambient temperature;
84% With pyridine In dichloromethane for 16h; Ambient temperature;
75% With dmap; triethylamine In dichloromethane at -5 - 20℃; Inert atmosphere;
With sodium hydroxide
With triethylamine In acetone for 1h; Heating;
In diethyl ether Ambient temperature; Yield given;
With morpholinomethyl polystyrene HL In dichloromethane at 20℃;
In N,N-dimethyl acetamide; water monomer at 0 - 20℃; for 1h; Inert atmosphere;
With triethylamine In dichloromethane at 0℃; for 3h;
1241 mg In dichloromethane at 0 - 20℃;
Stage #1: aniline With triethylamine In dichloromethane for 0.166667h; Cooling with ice; Stage #2: phenylacetyl chloride In dichloromethane for 2.25h;
With triethylamine In dichloromethane at 0℃;

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[10]Nagarajan, K.; Talwalker, P. K.; Kulkarni, C. L.; Shah, R. K.; Shenoy, S. J.; Prabhu, S. S. [Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1985, vol. 24, p. 83 - 97]
[11]Maran, Flavio; Celadon, Dino; Severin, Maria Gabriella; Vianello, Elio [Journal of the American Chemical Society, 1991, vol. 113, # 24, p. 9320 - 9329] McCarthy, Daniel G.; Hegarty, Anthony F. [Journal of the Chemical Society. Perkin transactions II, 1980, p. 579 - 591] Yamagami; Takao; Takeuchi [Chemical and Pharmaceutical Bulletin, 1983, vol. 31, # 11, p. 4172 - 4177] Shu; Chen; Heys [Journal of Organometallic Chemistry, 1996, vol. 524, # 1-2, p. 87 - 93]
[12]Buchstaller; Ebert; Anlauf [Synthetic Communications, 2001, vol. 31, # 7, p. 1001 - 1005]
[13]Cvetovich, Raymond J.; DiMichele, Lisa [Organic Process Research and Development, 2006, vol. 10, # 5, p. 944 - 946]
[14]Dong, Ying; Liu, Bangyu; Chen, Peng; Liu, Qun; Wang, Mang [Angewandte Chemie - International Edition, 2014, vol. 53, # 13, p. 3442 - 3446][Angew. Chem., 2014, vol. 126, # 13, p. 3510 - 3514,5]
[15]Rathore, Vandana; Sattar, Moh.; Kumar, Raushan; Kumar, Sangit [Journal of Organic Chemistry, 2016, vol. 81, # 19, p. 9206 - 9218]
[16]Pandia, Biplab Keshari; Gunanathan, Chidambaram [Journal of Organic Chemistry, 2021, vol. 86, # 15, p. 9994 - 10005]
[17]Chen, Yujie; He, Shuo; Huang, Zhi-Bin; Li, Bao; Shi, Da-Qing; Zhao, Yingsheng [Advanced Synthesis and Catalysis, 2022, vol. 364, # 9, p. 1555 - 1563]
  • 7
  • [ 103-82-2 ]
  • [ 6780-49-0 ]
  • [ 621-06-7 ]
  • 8
  • [ 103-82-2 ]
  • [ 6780-49-0 ]
  • [ 621-06-7 ]
  • [ 101-97-3 ]
  • [ 62-53-3 ]
  • [ 109-94-4 ]
  • 9
  • [ 103-82-2 ]
  • [ 102-07-8 ]
  • [ 621-06-7 ]
YieldReaction ConditionsOperation in experiment
67% With magnesium(II) nitrate hexahydrate In octane at 130℃; for 24h;
  • 10
  • [ 621-06-7 ]
  • [ 14181-75-0 ]
YieldReaction ConditionsOperation in experiment
With bromine; triethylamine; triphenylphosphine In tetrachloromethane for 5h; Heating;
Multi-step reaction with 2 steps 1: PCl5 / benzene / 1 h / Heating 2: NEt3 / benzene / 6 h / Heating
Multi-step reaction with 2 steps 1: phosphorus pentachloride / benzene / 1 h / 80 °C 2: triethylamine / benzene / 6 h / Reflux
  • 11
  • [ 621-06-7 ]
  • [ 1739-00-0 ]
YieldReaction ConditionsOperation in experiment
94% With lithium aluminium tetrahydride In 1,4-dioxane; diethyl ether
92% With borane-ammonia complex; boron trifluoride diethyl etherate; tris(pentafluorophenyl)borate In 1,2-dichloro-ethane at 60℃; for 24h;
Multi-step reaction with 2 steps 1: hydrogen; [2-((diphenylphospino)methyl)-2-methyl-1,3-propanediyl]bis[diphenylphosphine]; bis(trifluoromethanesulfonyl)amide; tris(2,4-pentanedionato)ruthenium(III) / dibutyl ether / 18 h / 160 °C / 45004.5 Torr / Autoclave 2: hydrogen; [2-((diphenylphospino)methyl)-2-methyl-1,3-propanediyl]bis[diphenylphosphine]; bis(trifluoromethanesulfonyl)amide; tris(2,4-pentanedionato)ruthenium(III) / dibutyl ether / 18 h / 160 °C / 45004.5 Torr / Autoclave
70 %Chromat. With cobalt(II) bis[bis((trifluoromethyl)sulfonyl)amide]; trimethylsilyl trifluoromethanesulfonate; (p-anisyl)triphos; hydrogen In n-heptane at 125℃; for 14h; Autoclave; Sealed tube;

  • 12
  • [ 621-06-7 ]
  • [ 74157-87-2 ]
YieldReaction ConditionsOperation in experiment
With phosphorus pentachloride In benzene for 1h; Heating;
With phosphorus pentachloride In benzene for 1h; Inert atmosphere; Reflux;
With phosphorus pentachloride In toluene Heating;
With phosphorus pentachloride In benzene at 80℃; for 1h;

  • 13
  • [ 6636-01-7 ]
  • [ 621-06-7 ]
YieldReaction ConditionsOperation in experiment
96% With Celite; silver carbonate In acetonitrile at 20℃; for 3h;
65% With sulfuric acid; dihydrogen peroxide; cobalt(II) chloride In isopropyl alcohol at 25℃; for 2h; pH 3-4;
65 % Chromat. With hydrogenchloride; N-nitrosopiperidine; potassium iodide In dichloromethane; water at 22℃; for 48h;
  • 14
  • [ 103-82-2 ]
  • [ 103-71-9 ]
  • [ 621-06-7 ]
  • [ 102-07-8 ]
YieldReaction ConditionsOperation in experiment
1: 50% 2: 31% With triethylamine In toluene at 60℃; for 2h;
  • 15
  • [ 136848-28-7 ]
  • [ 621-06-7 ]
YieldReaction ConditionsOperation in experiment
83% In dichloromethane; acetonitrile for 3h; Heating;
83% With silver hexafluoroantimonate; antimonypentachloride In acetonitrile for 3h; Heating;
  • 16
  • [ 621-06-7 ]
  • [ 33513-42-7 ]
  • [ 2859-30-5 ]
YieldReaction ConditionsOperation in experiment
65% Stage #1: N,N-dimethyl-formamide With trichlorophosphate at 0 - 20℃; for 0.5h; Stage #2: 2,N-diphenylacetamide at 5℃; for 24h; Reflux; Synthesis of 2-chloro-3-phenylquinoline, 4 Dimethyl formamide (3.85 mL, 0.05 mol) was cooled to 0 °C in a flask equipped with a dropping funnel. POCl3 (12.97 mL, 0.14 mol) was added dropwise from a dropping funnel with stirring. The resultant reagent was stirred for a further 30 min at RT and then cooled to 5°C. Thereafter, N-phenyl-benzylamide 3 (2.1 g,0.012 mol) was added and the stirring was further continued for 30 min; the reaction set-up was shifted to a water bath and reflexed for 24 h. After being subjected to the reaction conditions, the cooled reaction mixture was poured into crushed ice and neutralized with Na2CO3 solution. The solid 2-chloro-3-phenylquinoline 4 was filtered, dried and then purified by column chromatography. Yield 2.22 g(65%); m.p. 134°C; 1H NMR (CDCl3): δ 8.09 (m, 2H, C4and C8-H), 7.82 (d, 1H, J = 8.0 Hz, C5-H), 7.73 (t, 1H,J = 8.5 Hz, C7-H), 7.56(t, 1H, J = 7.0 Hz, C6-H), 7.39-7.51 (m, 5H, Ph-H); 13C NMR (CDCl3): δ 149.50,146.58, 139.16, 137.44, 134.86, 130.66, 129.68,128.36, 128.04, 127.98, 127.58, 127.47, 127.26, 123.56.
42% With trichlorophosphate at 75℃; for 5h;
  • 17
  • [ 62-53-3 ]
  • [ 101-41-7 ]
  • [ 621-06-7 ]
YieldReaction ConditionsOperation in experiment
92% With trimethylaluminum In tetrahydrofuran; toluene at 125℃; for 0.0333333h;
90% With indium (III) iodide at 110 - 120℃; for 8.5h;
88% With zinc In N,N-dimethyl-formamide for 0.1h; microwave irradiation;
83% With C18H15IMnN3O3; sodium t-butanolate In toluene at 120℃; for 18h; Inert atmosphere; Schlenk technique;
75% With 1,3,4,6,7,8-hexahydro-2H-pyrimido[1,2-a]pyrimidine at 75℃; for 12h;
With aluminum oxide; berberine chloride In benzene for 3h; Ambient temperature;

  • 18
  • [ 621-06-7 ]
  • C14H12(2)HNO [ No CAS ]
  • C14H12(2)HNO [ No CAS ]
YieldReaction ConditionsOperation in experiment
With deuterium In dichloromethane Ambient temperature;
With deuterium In dichloromethane Ambient temperature;
  • 19
  • [ 621-06-7 ]
  • [ 7472-70-0 ]
  • 1,3-Diphenyl-4-p-tolylamino-5-[(Z)-p-tolylimino]-1,5-dihydro-pyrrol-2-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
42% With n-butyllithium In tetrahydrofuran; hexane 0 deg C, 15 min; RT 2h;
  • 20
  • [ 74-96-4 ]
  • [ 621-06-7 ]
  • [ 42003-85-0 ]
  • [ 125576-06-9 ]
YieldReaction ConditionsOperation in experiment
1: 2.13 % Chromat. 2: 0.42 % Chromat. With potassium hydroxide In toluene at 60℃; for 2.5h;
  • 21
  • [ 19813-45-7 ]
  • [ 621-06-7 ]
YieldReaction ConditionsOperation in experiment
88% With silica gel In dichloromethane
  • 22
  • [ 101-97-3 ]
  • [ 62-53-3 ]
  • [ 621-06-7 ]
YieldReaction ConditionsOperation in experiment
98% With potassium <i>tert</i>-butylate; Aliquat 336 at 150℃; for 0.0333333h; microwave irradiation;
85% In neat (no solvent) at 130℃; for 6h; Synthesis of N-phenyl-benzylamide, 3 2-Phenylethyl ethanoate 2 (0.1 mol) was measured out and mixed with 0.1 mol of aniline 1 and was heated directly at 130 °C for 6 h. The solid which appeared was further purified by washing with chloroform and petroleum ether mixture, 85% yield of N-phenyl-benzylamide 3 was obtained. Yield 2.82 g (85%); m.p. 107°C;IR(KBr): 3284, 3059, 1657 cm-1; 1H NMR (CDCl3):δ 7.12-7.42 (m, 10H, (benzyl)-Ar-H (anilino)-Ar-H),7.06-7.10 (bs, 1H,-NH-H), 3.74 (s, 2H, COCH2-H); 13CNMR (CDCl3): δ 169.11, 137.61, 134.43, 129.58,129.30, 128.98, 128.50, 127.75, 124.51, 119.84,44.90.
83% With 1-(3-sulfopropyl)pyridinium phosphotungstate In neat (no solvent) at 120℃; for 0.833333h; Microwave irradiation; 4.3. Generalprocedure for the synthesis of amides Toa mixture of ester and amine in a 20 mL round bottomed flask was added [PyPS]3PW12O40(140 mg, 0.04 mmol). The reaction mixture was stirred at the corresponding temperature under MW (700 W). The progress of the reaction was monitored byTLC. On completion, the mixture was diluted with ethyl acetate (20 mL) with stirring for 30 min. The insoluble catalyst was recovered by filtration or centrifugation. The filtrate was evaporated and the residue in almost pureform. Recrystallization or column chromatography could be used for further purification.
  • 23
  • [ 621-06-7 ]
  • [ 6630-33-7 ]
  • 1,3-diphenylquinolin-2(1H)-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
33% With copper(l) iodide; potassium carbonate; N,N`-dimethylethylenediamine In toluene at 150℃; for 18h;
  • 24
  • [ 103-80-0 ]
  • [ 1227476-15-4 ]
  • [ 621-06-7 ]
YieldReaction ConditionsOperation in experiment
96% With samarium diiodide In tetrahydrofuran at 65℃; for 0.1h;
  • 25
  • [ 621-06-7 ]
  • [ 835-38-1 ]
YieldReaction ConditionsOperation in experiment
60% In acetonitrile at 20℃; for 24h; Irradiation;
  • 26
  • [ 103-80-0 ]
  • [ 17082-12-1 ]
  • [ 621-06-7 ]
YieldReaction ConditionsOperation in experiment
95% With samarium; titanium tetrachloride In tetrahydrofuran at 65℃; for 0.1h;
  • 27
  • [ 103-82-2 ]
  • [ 621-06-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: thionyl chloride / benzene
Multi-step reaction with 2 steps 1: SOCl2 / CHCl3
Multi-step reaction with 2 steps 1: (C2H5)3N, SO2ClF / CH2Cl2 / 1 h / Ambient temperature 2: 2 h / Ambient temperature
Multi-step reaction with 2 steps 1: sodium hydroxide; thionyl chloride / N,N-dimethyl acetamide; water / 0.42 h / -5 °C / Inert atmosphere 2: N,N-dimethyl acetamide; water / 1 h / 0 - 20 °C / Inert atmosphere
Multi-step reaction with 2 steps 1: dicyclohexyl-carbodiimide / tetrahydrofuran; dichloromethane / Cooling with ice 2: chloroform
Multi-step reaction with 2 steps 1.1: thionyl chloride; triethylamine / dichloromethane / 0.33 h / 0 °C / Inert atmosphere 1.2: 0 °C / Inert atmosphere 2.1: potassium tetrachloropalladate(II) / isopropyl alcohol / 24 h / 80 °C / Inert atmosphere
Multi-step reaction with 2 steps 1: sulfuric acid / 3 h / 75 °C 2: neat (no solvent) / 6 h / 130 °C
Multi-step reaction with 2 steps 1: thionyl chloride / dichloromethane; N,N-dimethyl-formamide / 1 h / 20 °C / Inert atmosphere 2: dichloromethane / 0 - 20 °C
Multi-step reaction with 2 steps 1: 1,2-dichloro-ethane / 5 h / 20 °C 2: N,N-dimethyl-formamide / 24 h / 20 °C

  • 28
  • [ 103-80-0 ]
  • [ 621-06-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: acetic acid anhydride 2: pyridine
Multi-step reaction with 2 steps 1: acetic acid anhydride 2: 180 °C
Multi-step reaction with 2 steps 1: water; KSH 2: 100 °C
20.07 g (95%) With pyridine; hydrogenchloride; aniline In dichloromethane; water 1 N-Phenyl 2-Phenylacetamide (IVa) EXAMPLE 1 N-Phenyl 2-Phenylacetamide (IVa) To a stirred solution of 9.3 g (0.10 Mole) of aniline (IIIa) and 8.3 g (0.10 Mole) pyridine in 100 mL CH2 Cl2 at 0° C. under an argon atmosphere was added a solution of 15.5 g (0.10 Mole) phenylacetyl chloride (IIa) in 25 mL CH2 Cl2 over a 30 minute period. The solution was allowed to warm to 25° C. over 1 hour and was quenched into 200 mL H2 O. The aqueous layer was washed with two 100 mL portions of CH2 Cl2 and the combined organic layers were washed with two 100 mL portions of 10% HCl solution The organic extract was dried over MgSO4, filtered, concentrated, and crystallized from CH2 Cl2 /hexane to give 20.07 g (95%) of colorless needles. mp. 115°-116° C. δ1 H-NMR (CDCl3) ppm 7.0-7.6 (m,11 H); 3.67 (S,2 H).

  • 29
  • [ 621-06-7 ]
  • [ 4732-66-5 ]
YieldReaction ConditionsOperation in experiment
89% With tetra(n-butyl)ammonium hydrogensulfate; sodium hydrogencarbonate In 1,4-dioxane for 12h; Reflux; Synthesis of 2-oxo-N, 2-diphenylacetamide (2a). To a 25 mL round-bottom flask, N,2-diphenylacetamide 1a (105.5 mg, 0.5 mmol), NaHCO3 (126mg, 1.5 mmol), and n-Bu4NHSO4 (254.7 mg, 0.75 mmol) in dioxane (2.5 mL) were added in the presence of atmospheric oxygen which was dried through a calcium chloride tube. The reaction mixture was stirred for 12 h under reflux until 1a disappeared monitored by TLC. After that, the mixture was filtered and washed with EA. The filtrate was concentrated under reduced pressure and the crude product was purified by column chromatography on silica gel (eluent: petroleumether/ethyl acetate = 5:1) to give 2a (101 mg, 89%) as a light yellow solid. m.p. 43-45 °C. IR (KBr): 3436, 3338, 3059, 2925, 1667, 1596, 1281 cm-1. 1H NMR (500 MHz, CDCl3): δ 9.04 (s,1H), 8.40 (dd, J = 7.5, 1.0 Hz, 2H), 7.71 (d, J = 7.5 Hz, 2H), 7.66-7.63 (m, 1H), 7.50 (t, J = 8.0Hz, 2H), 7.39 (t, J = 8.0 Hz, 2H), 7.19 (t, J = 7.5 Hz, 1H). 13C NMR (125 MHz, CDCl3): δ 187.57,159.09, 136.76, 134.71, 133.16, 131.53, 129.30, 128.65, 125.38, 120.06. MS (EI): m/z (%) 225(27) [M+], 211 (10), 120 (10), 119 (10), 106 (21), 105 (100), 91 (18), 77 (47).
70% With 18-crown-6 ether; potassium superoxide In N,N-dimethyl-formamide at 0 - 20℃; for 0.5h; Inert atmosphere; 4.2. General procedure B: synthesis of ketoamides General procedure: A pre-cooled solution of N-2-diphenylacetamide (100 mg, 0.47 mmol) in DMF (3 mL), 18-crown-6 (150 mg, 0.56 mmol), followed by KO2 (100 mg,1.41 mmol) was added at 0 C, reaction mass immediately turns to brown color. Reaction mass warmed to room temperature, stirred for 30 min and or until completion of starting material (monitored by TLC). Reaction mass was poured on ice, extracted with ethyl acetate (3 X 25 mL). The combined organicwas washed with H2O (2 X 5 mL), brine solution (5 mL) and dried over Na2SO4 and evaporated under vacuum. The crude material thus obtained was purified by column chromatography (silica gel 230-400 mesh, ethyl acetate - pet ether) to afford corresponding aketoamide.
Multi-step reaction with 2 steps 1: sodium / versetzt das Reaktionsgemisch mit Alkohol und mit einer 1,2 Mol Aethylformiat und zerlegt die entstandene Natriumverbindung mit eiskalter Schwefelsaeure 2: permanganate; acetone
  • 30
  • [ 451-40-1 ]
  • [ 621-06-7 ]
YieldReaction ConditionsOperation in experiment
85% With methanesulfonic acid; tetrabutylammoniun azide In 1,2-dimethoxyethane at 80℃; for 0.0833333h; Flow reactor;
43% With nitromethane; trifluoromethylsulfonic anhydride; acetic acid In formic acid at 80 - 120℃; 25 Example 6 p-Methoxyacetanilide Take a reaction tube, add 60-100mg (1.2mmol) of nitromethane, 50-60mg (0.3mmol) of phenyl phenylmethyl ketone 0.5mL of acetic acid,Trifluoromethanesulfonic anhydride 150-200mg (0.6mmol), formic acid 30-60mg (0.75mmol), stirred at 80-120°C for 1-72 hours. After the reaction, 10 mL of sodium hydroxide solution was added to quench the reaction, extracted with ethyl acetate 3 times, the organic phase was washed with 5 mL of brine, and the organic phases were combined and separated by column chromatography to obtain 27.2 mg of 2-phenylacetanilide, with a yield of 43% .
43% With formic acid; nitromethane; trifluoromethylsulfonic anhydride In acetic acid at 100℃; for 12h;
Multi-step reaction with 2 steps 1: alcohol; hydroxylamine 2: PCl5; diethyl ether
Multi-step reaction with 2 steps 1: sodium acetate; hydroxylamine hydrochloride / ethanol; water / Reflux 2: zinc trifluoromethanesulfonate; phthalic anhydride / acetonitrile / 20 °C / Inert atmosphere

  • 31
  • O-ethylthiobenzoate [ No CAS ]
  • [ 621-06-7 ]
  • 2,3,N-triphenyl-3-mercaptopropenamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
With lithium diisopropyl amide In tetrahydrofuran; cyclohexane 10.B Part B Part B 2,3,N-triphenyl-3-mercaptopropenamide A mixture of 1.27 g (6.02 mmol) phenylacetanilide and 20 mL tetrahydrofuran was stirred at 0° C. Lithium diisopropylamide (4.4 mL of 1.5M in cyclohexane, 1.1 equivs.) was added dropwise and the solution stirred 15 mins. followed by stirring at room temperature for 15 mins. The mixture was then cooled to 0° C. and 1.00 g (6.02 mmol) O-ethylthiobenzoate (S. O. Lawesson, et. al., Bull. Soc. Chim. Belg. 87 (4), 293 (1978)) was added dropwise in 10 mL tetrahydrofuran. After addition was complete, the ice bath was removed and the solution stirred 30 mins. followed by stirring at reflux for 48 hrs. The solution was allowed to cool to room temperature and poured into 50 mL water. The aqueous layer was acidified with concentrated hydrochloric acid to yield a reddish-orange solid. The solid was recrystallized from absolute ethanol to provide 0.16 mg (0.48 mmol, 8%) 2,3,N-triphenyl-3-mercaptopropenamide as a pale, yellow solid, mp=144°-146° C.(d). NMR (CDCl3 /TMS): 5.20 (s, 1H), 7.07-7.41 (m, 16H). IR (KBr): 3400, 3302, 1658.
  • 32
  • [ 621-06-7 ]
  • [ 105-36-2 ]
  • [ 134581-47-8 ]
  • [ 134581-51-4 ]
YieldReaction ConditionsOperation in experiment
80% In N,N-dimethyl-formamide 2 1,5-dihydro 1,3-diphenyl-4 hydroxy-2H-pyrrol-2-one (Va) EXAMPLE 2 1,5-dihydro 1,3-diphenyl-4 hydroxy-2H-pyrrol-2-one (Va) To a stirred slurry of 500 mg (12 mmol) of a 60% oil dispersion of sodium hydride (which had been washed with hexane) in 12 ml dry DMF under argon atmosphere was added 1.06 g (5.0 mmol) of N-phenyl-2-phenyl acetamide (IVa) in 5 mL dry DMF. Gas evolution had ceased after 30 minutes and 0.560 mL(5.0 mmol) of ethyl bromoacetate was added via syringe. The solution was stirred at 25° C. for 30 minutes, then warmed to 80° C. for 4 hours. The cooled solution was carefully poured into 200 mL H2 O, washed with ether, filtered over celite and acidified to pH=2. The white precipitate was filtered, washed well with H2 O and dried under high vacuum to give 1.04 g (4.0 mmol, 80% yield) of 1,3-diphenyl-2,4-pyrrolidinedione Ia, mp 285°-287° C. (Dec.): IR(KBr) 3500-2400 (b, OH), 1620, 1400 cm-1; 1 H-NMR (DMSO) ppm δ 7.99 (d, 2 H, J=6 Hz), 7.73 (d,2 H, J=6 Hz), 7.37 (t, 4 H, J=6 Hz), 7.19 (t, 1 H, J=6 Hz), 7.05 (t, 1 H, J=6 Hz), 4.48 (s, 2 H).
  • 33
  • sodium methoxide (NaOCH3) [ No CAS ]
  • [ 621-06-7 ]
  • [ 85803-62-9 ]
  • 3-[2-(4-methylpiperazin-1-yl)phenyl]-2,N-diphenylacrylamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
With sodium methylate; In methanol; ethyl acetate; N,N-dimethyl-formamide; benzene; EXAMPLE 1 3-[2-(4-Methylpiperazin-1-yl)phenyl]2,N-diphenylacrylamide To a mixture of <strong>[85803-62-9]2-(4-methylpiperazin-1-yl)benzaldehyde</strong> (0.157 g, 0.77 mmol), 2,N-diphenylacetamide (0.162 g, 0.77 mmol), benzene (1.0 mL) and N,N-dimethylformamide (1.1 mL) was added anhydrous sodium methoxide (0.087 g, 1.62 mmol). Under a nitrogen atmosphere (N2), the mixture was heated to 80° C. for 16 hours, at which time another 46 mg of sodium methoxide (NaOCH3) was added and heating continued at 130° C. for 7 hours. The reaction was cooled to room temperature and was diluted with ethyl acetate (EtOAc), washed twice with 1N lithium chloride (LiCl), once with saturated aqueous sodium chloride, and dried over calcium sulfate (CaSO4). After filtration, the crude product was absorbed onto 450 mg of silica gel and added to a 4.0*8 inch column packed with silica gel and ethyl acetate. Elution with ethyl acetate (200 mL) followed by 1percent methanol: 99percent ethyl acetate (100 mL) gave 35 mg of a light yellow oil which was crystallized from methylene chloride:hexanes to give the title product, 5 mg, as a yellow powder. Mass spectrum: 398 (M+1); 1H-NMR (CDCl3, 300 MHz) delta 7.61 (2H, dd), 7.52 (1H, d, J=7.69 Hz), 7.50-7.26 (10H, m), 7.04 (3H, m), 3.14-3.14 (4H, m), 2.57 (4H, br s), 2.33 (3H, s).
  • 34
  • [ 591-50-4 ]
  • [ 103-81-1 ]
  • [ 621-06-7 ]
YieldReaction ConditionsOperation in experiment
78% With copper(I) thiophene-2-carboxylate; sodium t-butanolate In dimethyl sulfoxide at 100℃; for 6h; Inert atmosphere;
72% With copper(ll) sulfate pentahydrate; sodium ascorbate; sodium t-butanolate In dimethyl sulfoxide at 100℃; for 7h; 1 General procedure for N-arylation of primary amides General procedure: CuSO4*5H2O (0.15 mmol), NaAsc (0.3 mmol), aryl iodides (1mmol), primary amides (1.2mmol), t-BuONa (2.0 mmol), and DMSO (3mL) were added to a flask. The reaction mixture was stirred under air, and then cooled to room temperature and extracted with ethyl acetate (3×10 mL). The organic layer was then dried over anhydrous Na2SO4, and the solvent was removed under reduced pressure. The secondary amides were finally obtained by column chromatography on silica gel eluted with ethyl acetate/petroleum ether.
70% With cobalt(II) oxalate dihydrate; caesium carbonate; N,N`-dimethylethylenediamine In water at 130℃; for 24h; Green chemistry; General Procedure for N-Arylation of Pyrrolidinone/AliphaticAmides: General procedure: A mixture of cobalt(II) oxalate dihydrate(Sigma-Aldrich, 0.294 mmol), Cs2CO3 (2.94 mmol), pyrrolidinoneor aliphatic amide (1.47 mmol), DMEDA (0.588 mmol),distilled H2O (0.3 mL) and aryl halide (2.205 mmol) were addedto an 8.0-mL reaction vial fitted with a Teflon-sealed screw cap.The reaction mixture was stirred under air in a closed system at120 °C and 130 °C, respectively for 24 h. The heterogeneousmixture was subsequently cooled to r.t. and diluted withCH2Cl2. The combined organic extracts were dried over anhydNa2SO4, filtered and the solvent was removed under reducedpressure. The crude product was loaded into the column usingminimal amounts of CH2Cl2 and was purified by silica gel column chromatography to afford the N-arylated product. Theidentity and purity of products were confirmed by 1H NMR and13C NMR spectroscopic analysis.
69% With dimethylenecyclourethane; copper(l) iodide; sodium methylate In dimethyl sulfoxide at 120℃; for 24h;

  • 35
  • [ 369-57-3 ]
  • [ 140-29-4 ]
  • [ 621-06-7 ]
YieldReaction ConditionsOperation in experiment
97% Stage #1: benzenediazonium tetrafluoroborate; phenylacetonitrile for 0.0166667h; Microwave irradiation; Stage #2: With water In diethyl ether
  • 36
  • [ 60-12-8 ]
  • [ 62-53-3 ]
  • [ 621-06-7 ]
YieldReaction ConditionsOperation in experiment
51% With oxygen; lithium hydroxide In water at 80℃; for 12h;
35% With [RuCl2(p-cymene)(iPr2-imy)]; potassium <i>tert</i>-butylate; tricyclohexylphosphine In toluene at 110℃; for 24h; Inert atmosphere;
35% With potassium <i>tert</i>-butylate In 1,3,5-trimethyl-benzene for 24h; Inert atmosphere; Reflux; 10 General Amidation Procedure Using an Isolated Ru-Complex; The isolated Ru(p-cymene)Cl2IiPr complex (0.025 mmol), PCy3 (0.025 mmol) and KOtBu (0.05 mmol) were weighted into an oven-dried Schlenk tube. A condenser was attached and vacuum applied before the flask was filled with argon (repeat twice). Freshly distilled toluene (1 mL) was then added and the mixture was heated at reflux temperature for 20 min. The flask was removed from the oil bath and the alcohol (0.5 mmol) and the amine (0.5 mmol) were added. The flask was returned to the oil bath and heated at reflux for 24 hours. After cooling to room temperature, the solvent was removed in vacuo and the residue was purified by column chromatography to give the amide. Results are presented in FIG. 7.
34% With dichloro(η6-p-cymene)(1,3-dimethylimidazole-2-ylidene)ruthenium; potassium <i>tert</i>-butylate In 1,3,5-trimethyl-benzene at 163℃; for 24h; Inert atmosphere;
34% In toluene for 24h; Inert atmosphere; Reflux; Alkaline conditions; 14 General Procedure for Amide Synthesis using 46-50; In an argon- filled glovebox, a 10 mL oven-dried Schlenk tube was charged with complex 46, 47, 48, 49 or 50 (0.025 mmol), base (0.075 mmol), and 0.6 mL of toluene. The Schlenk tube was then taken out, and alcohol (0.50 mmol) and amine (0.55 mmol) were added. The reaction mixture was heated to reflux under a flow of argon to facilitate removal of hydrogen for 24 h before being cooled to room temperature. All the volatiles were removed under vacuum. Purification of the crude product by flash chromatography afforded amides. All the amides were identified by spectral comparison with literature data (Naota et al., 1991, supra; Watson et al, 2009, supra; Nordstroem et al., 2008, supra).; Substrate Scope [0094] Complex 46, with smaller wingtip groups of NHC, was chosen to expand the substrate scope, expecting improvement for challenging sterically hindered substrates. A range of amides were synthesized with good to excellent yields with precatalyst 46 (Fig. 9). Excellent yields were obtained for sterically nonhindered substrates (entries 1, 2). Modestly hindered substrates worked reasonably well (entries 3, 4).[0095] Cyclic secondary amines such as 21 and 22 also reacted smoothly, producing the corresponding amides with good yields (entries 5, 6). In particular, five- to sevenmembered cyclic lactams, 29, 30, and 31, were synthesized efficiently from α,ω-amino alcohols (entries 7-9). The electronic effect on alcohols was studied using benzyl alcohol derivatives. Slighlty reduced yields were observed with electron-deficient substrates (entries 10-12). However, rather disappointingly, it also showed a similar limitation on sterically bulky substrates and less basic aniline, demonstrating challenges in this area (entries 13, 14; Gunanathan et al, 2007, supra; Naota et al., 1991, supra; Watson et al., 2009, supra; Nordstroem et al., 2008, supra). Catalytic Intermediates
25% With dichloro(benzene)ruthenium(II) dimer; sodium hydride; acetonitrile; 1,3-di(propan-2-yl)-1H-imidazol-3-ium bromide In 1,3,5-trimethyl-benzene at 163℃; for 36h; Inert atmosphere;
21% With cyclooctadiene ruthenium(II) dichloride; potassium <i>tert</i>-butylate; 1,3-diisopropyl-1H-imidazol-3-ium chloride; tricyclopentylphosphonium tetrafluoroborate In 1,3,5-trimethyl-benzene for 24h; Inert atmosphere; Reflux;
19% Stage #1: 2-phenylethanol; aniline With pyridine; ruthenium trichloride; C17H25N2(1+)*I(1-); sodium hydride In toluene for 24h; Inert atmosphere; Reflux; Stage #2: In toluene

  • 37
  • [ 7032-25-9 ]
  • [ 201230-82-2 ]
  • [ 100-39-0 ]
  • C20H16N2O [ No CAS ]
  • C20H16N2O [ No CAS ]
  • [ 621-06-7 ]
YieldReaction ConditionsOperation in experiment
With palladium diacetate; triethylamine; triphenylphosphine In tetrahydrofuran at 100℃; for 1h; stereoselective reaction;
  • 38
  • [ 201230-82-2 ]
  • [ 100-39-0 ]
  • [ 62-53-3 ]
  • [ 91-73-6 ]
  • [ 758640-21-0 ]
  • [ 621-06-7 ]
YieldReaction ConditionsOperation in experiment
With palladium diacetate; triphenylphosphine In tetrahydrofuran at 110℃; for 10h;
  • 39
  • [ 201230-82-2 ]
  • [ 100-44-7 ]
  • [ 62-53-3 ]
  • [ 758640-21-0 ]
  • [ 621-06-7 ]
YieldReaction ConditionsOperation in experiment
With palladium diacetate; triphenylphosphine In tetrahydrofuran at 110℃; for 15h;
  • 40
  • [ 103-82-2 ]
  • [ 701-73-5 ]
  • [ 621-06-7 ]
YieldReaction ConditionsOperation in experiment
88% With 1,8-diazabicyclo[5.4.0]undec-7-ene In N,N-dimethyl-formamide at 60℃; for 0.05h; Microwave irradiation;
  • 41
  • [ 201230-82-2 ]
  • [ 1666-17-7 ]
  • [ 62-53-3 ]
  • [ 621-06-7 ]
YieldReaction ConditionsOperation in experiment
84% Stage #1: benzaldehyde p-toluenesulfonylhydrazone With sodium hydride In toluene at 0 - 20℃; for 0.5h; Inert atmosphere; Stage #2: carbon monoxide; aniline With tris-(dibenzylideneacetone)dipalladium(0); potassium carbonate In toluene at 60℃; for 24h;
  • 42
  • [ 201230-82-2 ]
  • [ 100-52-7 ]
  • [ 62-53-3 ]
  • [ 621-06-7 ]
YieldReaction ConditionsOperation in experiment
73% Stage #1: benzaldehyde With sodium sulfate; toluene-4-sulfonic acid hydrazide In toluene at 60℃; for 0.0833333h; Inert atmosphere; Stage #2: carbon monoxide; aniline With tris-(dibenzylideneacetone)dipalladium(0); lithium tert-butoxide In toluene at 60℃; for 23h;
  • 43
  • [ 2142-69-0 ]
  • [ 621-06-7 ]
  • [ 1315568-19-4 ]
YieldReaction ConditionsOperation in experiment
64% With copper(l) iodide; caesium carbonate; ethylenediamine In toluene at 110℃; for 24h; Inert atmosphere; Sealed tube;
  • 44
  • [ 621-06-7 ]
  • [ 1371615-24-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: phosphorus pentachloride / benzene / 1 h / 80 °C 2: triethylamine / benzene / 6 h / Reflux 3: [Cu(CH3CN)2(PPh3)2][ClO4]; triphenylphosphine / dichloromethane / 25 °C
  • 45
  • [ 60-12-8 ]
  • [ 622-37-7 ]
  • [ 621-06-7 ]
YieldReaction ConditionsOperation in experiment
22% With dihydridotetrakis(triphenylphosphine)ruthenium; sodium hydride; acetonitrile; 1,3-di(propan-2-yl)-1H-imidazol-3-ium bromide In 1,3,5-trimethyl-benzene for 48h; Reflux; Inert atmosphere; Schlenk technique; Glovebox;
  • 46
  • [ 140-29-4 ]
  • [ 62-53-3 ]
  • [ 621-06-7 ]
YieldReaction ConditionsOperation in experiment
77% With copper doped mesoporous polymelamine-formaldehyde In water at 80℃; for 14h;
72% Stage #1: aniline With tetrafluoroboric acid In water Inert atmosphere; Stage #2: phenylacetonitrile With potassium phosphate; water at 80℃; for 12h; General procedure General procedure: A mixture of aryl diazonium tetrafluoroborates compounds (0.5 mmol), nitriles (0.5 mmol), H2O (1.5 mmol) and K3PO4 (0.6 mmol) was dissolved in acetonitrile (1.0 mL) or ethyl acetate (1.0 mL) under N2 atmosphere, stirred at 80 oC for 12h. Removal of the solvent under a reduced pressure gave the crude product; pure product was obtained by passing the crude product through a short silica gel column using Hexane/EtOAc (1:1-2:1) as eluent.
71% With water; copper diacetate; pipecolic Acid at 100℃; for 18h; 2. General procedure for the catalytic reaction General procedure: Nitrile (1 mmol), amine (1.3 mmol), Cu(OAc)2 (0.1 mmol), and the ligand 2-piperidinecarboxylic acid (0.2 mmol) in water (5mL) were put into a teflon septum screw-capped tube. The reaction mixture was stirred at 100 °C for 18 h without an inert gas atmosphere and then cooled to room temperature and extracted with dichloromethane. The organic layer was dried over Na2SO4 and the solvent was removed under reduced pressure. The residue was purified by silica-gel column chromatography to afford the corresponding product
  • 47
  • [ 62-53-3 ]
  • [ 83-13-6 ]
  • [ 621-06-7 ]
YieldReaction ConditionsOperation in experiment
90% Stage #1: aniline; diethyl 2-phenylmalonate at 100 - 130℃; Stage #2: With caesium carbonate In 1,4-dioxane at 100℃;
  • 48
  • [ 201230-82-2 ]
  • [ 62-53-3 ]
  • [ 108-88-3 ]
  • [ 621-06-7 ]
YieldReaction ConditionsOperation in experiment
62% With di-tert-butyl peroxide; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; palladium dichloride at 125℃; for 24h; Autoclave;
34% With dichloro[4,5-bis(diphenylphosphino)-9,9’-dimethylxanthene]palladium(II) at 120℃; for 16h; Autoclave; Inert atmosphere;
  • 49
  • [ 501-65-5 ]
  • [ 621-06-7 ]
YieldReaction ConditionsOperation in experiment
89% With (triphenylphosphine)gold(I) chloride; trimethylsilylazide; water; silver carbonate; trifluoroacetic acid In 1,2-dichloro-ethane at 60℃; Schlenk technique; Inert atmosphere;
88% With trimethylsilylazide; silver carbonate; trifluoroacetic acid In water; 1,2-dichloro-ethane at 60℃; for 12h; Schlenk technique; Inert atmosphere;
73% With formic acid; nitromethane; trifluoromethylsulfonic anhydride In acetic acid at 100℃; for 12h;
62% With sodium azide; C16H17AuBrN3O; water; trifluoroacetic acid In 1,2-dichloro-ethane at 25℃; for 2h; Schlenk technique; Inert atmosphere; 6.3. General procedure for catalysis General procedure: Alkynes (0.5 mmol), NaN3 (1 mmol), H2O (1 mmol), catalyst 1(2 mol%) and TFA/DCE (2 mL, 1:1 v/v) were taken in a Schlenk tube inside a fume hood. The reaction mixture was allowed to stir for 2 h at room temperature. Then 25 mL water was added to it and theorganics were extracted with ethyl acetate (3 x 10 mL). The solventwas evaporated under reduced pressure. The residue was purifiedby column chromatography on silica gel (petroleum ether/ethylacetate) to give the desired amide product. Yields were calculatedbased on isolated products. GC yields were reported in presence ofinternal standard dodecane.

  • 50
  • [ 201230-82-2 ]
  • sodium 2-benzylidene-1-tosylhydrazin-1-ide [ No CAS ]
  • [ 62-53-3 ]
  • [ 621-06-7 ]
YieldReaction ConditionsOperation in experiment
95% With 1,4-diaza-bicyclo[2.2.2]octane; cobalt(II) tetramethyldibenzotetraaza[14]annulene In toluene at 60℃; for 16h; Inert atmosphere; Autoclave;
75% With potassium phosphate; cobalt(II) 5,10,15,20-tetraphenylporphyrin; Aliquat<SUP> </SUP>(at)366 In toluene at 50℃; for 18h; Inert atmosphere; Autoclave;
  • 51
  • [ 103-82-2 ]
  • [ 814-49-3 ]
  • [ 62-53-3 ]
  • [ 621-06-7 ]
YieldReaction ConditionsOperation in experiment
60% Stage #1: phenylacetic acid; diethyl chlorophosphate With triethylamine In tetrahydrofuran at 15 - 20℃; for 3h; Stage #2: aniline In tetrahydrofuran at 20 - 25℃; for 1h;
  • 52
  • [ 591-50-4 ]
  • [ 140-29-4 ]
  • [ 621-06-7 ]
YieldReaction ConditionsOperation in experiment
79% With copper(l) iodide; water; potassium carbonate; 3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate; sodium hydroxide; N,N`-dimethylethylenediamine at 100℃; for 3h; Inert atmosphere; Sealed tube; 4.3. General procedure 2: for the N-arylation between iodobenzeneand substituted benzonitriles (3m-s) General procedure: To a screw-capped vial (50 ml) were added iodobenzene 1a(1.0 mmol), substituted benzonitrile 2 (2.0 mmol), K2CO3 (276 mg,2.0 mmol), NaOH (40 mg,1.0 mmol), CuI (19 mg, 0.1 mmol), DMEDA(9 mg, 0.1 mmol), and [bmim]PF6 (14 mg, 0.05 mmol) in water(2 ml). The vial was flushed with nitrogen then sealed with the cap,and allowed to stir at 100 C for the specific reaction time. Thereaction mixture was extracted with EtOAc (315 ml). The combinedorganic extracts were dried over Na2SO4 for 12 h and evaporatedunder vacuum. The crude products were purified in a silicagel column for further purification, using PE/EtOAc (5:1) as theeluent.
  • 53
  • [ 621-06-7 ]
  • [ 95-92-1 ]
  • [ 5347-00-2 ]
YieldReaction ConditionsOperation in experiment
With potassium <i>tert</i>-butylate In tetrahydrofuran at 0℃; for 3h; 2.5 (5) The synthesis of 3-hydroxy-1,4-diphenyl-1H-pyrrole-2,5-dione (6a) [0230] After the addition of anhydride THF (20 ml) to compound 5a (1.55 g, 7.34 mmol), the temperature was adjusted to 0° C. Diethyloxalate (1.45 g, 9.50 mmol) and potassium t-butoxide (1.35 g, 11.9 mmol) were added thereto and the agitation for 3 hours was carried out. After the identification of the reaction progress with TLC, the solution was poured into the distilled water and acidified with 1N HCL aqueous solution. Three times extractions were carried out with EA and three times washings were carried out with brine. Water was removed by using Na2SO4, solvents were removed and then, the suspension was carried out by HX.
  • 54
  • [ 62-53-3 ]
  • (isopropylideneamino) 2-phenylacetate [ No CAS ]
  • [ 621-06-7 ]
YieldReaction ConditionsOperation in experiment
81% With CAL-B In tert-butyl methyl ether at 55℃; for 8h; Green chemistry; Enzymatic reaction; chemoselective reaction;
  • 55
  • [ 103-82-2 ]
  • (±)-N-phenylprop-2-ene-1-sulfinamide [ No CAS ]
  • [ 621-06-7 ]
YieldReaction ConditionsOperation in experiment
With dmap In chloroform at 70℃; for 6h; Inert atmosphere;
  • 56
  • [ 621-06-7 ]
  • [ 103-81-1 ]
  • [ 62-53-3 ]
YieldReaction ConditionsOperation in experiment
95 %Chromat. With phosphoric acid; ammonia In ethylene glycol at 145℃; for 15h;
94 %Chromat. With phosphoric acid; ammonia In ethylene glycol at 145℃; for 15h;
  • 57
  • [ 1011269-13-8 ]
  • [ 621-06-7 ]
YieldReaction ConditionsOperation in experiment
85% With water; trifluoroacetic acid In dichloromethane at 20℃; for 3h; 2.2. General procedure for the preparation of amides 2; Typical Procedure II General procedure: The reaction of ynamides 1 (0.3 mmol), TFA (67 μL), H2O (27 μL) and DCM (2.0 mL) was carried out at room temp. for 3-5 h, as the progress of the reaction was monitored by TLC analysis. Upon completion, the mixture was diluted with H2O (10 mL). The resulting mixture was extracted with DCM (3×10 mL), and the combined extracts were dried with anhydrous Na2SO4. The solvent was removed by evaporation under reduced pressure. The crude product was purified by flash chromatography on a silica gel column (petroleum ether/ethyl acetate) to afford amides 2. N,2-diphenylacetamide (2a): yield 85 % (53.7 mg); White solid. Mp 116-117 °C (n-hexane/ethyl acetate). 1H NMR (400 MHz, CDCl3) δ7.40 (t, J = 8.0 Hz, 4H), 7.36-7.30 (m, 3H), 7.27 (t, J = 7.6 Hz, 2H), 7.16 (s, 1H), 7.08 (t, J = 7.6 Hz, 2 H), 3.72 (s, 2H); 13C NMR (100 MHz, CDCl3) δ 169.0, 137.6, 134.4, 129.5, 129.2, 128.9, 127.7, 124.4, 119.8, 44.8; HRMS (ESI+): m/z calcd. for C14H13NO (M++ Na) 234.0889, found 234.0884. Crystal data for 2a: C14H13NO; M = 211.25; Monoclinic; space group P21/n; final R indices [I>2σ(I)]: R1=0.0379, wR2=0.0915, R indices(all data): R1=0.0536, wR2=0.1017, a = 5.6832(5) Å, b = 25.278(2) Å, c = 8.0124(7)Å; β = 91.916(2)°, V = 1150.44(17) Å3; T= 296 K; Z = 4; reflection measured/independent: 6372/2032 (Rint = 0.022), number of observations [I>2σ(I)]: 1561, parameters: 145.
76% With water; trifluoroacetic acid In acetonitrile at 20℃; for 12h;
  • 58
  • [ 524-38-9 ]
  • [ 621-06-7 ]
  • 2-(1,3-dioxoisoindolin-2-yloxy)-N,2-diphenylacetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
30% With [bis(acetoxy)iodo]benzene In dichloromethane at 20℃; for 4h; Schlenk technique; Inert atmosphere;
  • 59
  • [ 4732-66-5 ]
  • [ 621-06-7 ]
YieldReaction ConditionsOperation in experiment
96% With potassium tetrachloropalladate(II) In isopropyl alcohol at 80℃; for 24h; Inert atmosphere; chemoselective reaction;
  • 60
  • [ 4732-66-5 ]
  • [ 621-06-7 ]
  • N-phenyl-2-hydroxy-4-phenylacetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
1: 10% 2: 51% With palladium dichloride; HSiPh3 In methanol at 60℃; for 24h;
  • 61
  • [ 621-06-7 ]
  • [ 60-12-8 ]
  • [ 1739-00-0 ]
  • [ 62-53-3 ]
YieldReaction ConditionsOperation in experiment
1: 62% 2: 62% 3: 20% With tris(2,4-pentanedionato)ruthenium(III); hydrogen; bis(trifluoromethanesulfonyl)amide; [2-((diphenylphospino)methyl)-2-methyl-1,3-propanediyl]bis[diphenylphosphine] In dibutyl ether at 160℃; for 18h; Autoclave;
65 %Chromat. With tris(2,4-pentanedionato)ruthenium(III); ytterbium(III) trifluoromethanesulfonate nonohydrate; hydrogen; [2-((diphenylphospino)methyl)-2-methyl-1,3-propanediyl]bis[diphenylphosphine] In 1,4-dioxane at 150℃; for 60h; Autoclave;
  • 62
  • [ 621-06-7 ]
  • [ 60-12-8 ]
  • [ 62-53-3 ]
YieldReaction ConditionsOperation in experiment
1: 93 %Chromat. 2: 94 %Chromat. With {Ru(H)(BH4)(CO)(3-(di-tert-butylphosphino)-N-((1-methyl-1H-imidazol-2-yl)methyl)propylamine)}; hydrogen In isopropyl alcohol at 150℃; for 18h; Autoclave;
1: 98 %Chromat. 2: 94 %Chromat. With C16H25MnN3O3P(1+)*Br(1-); potassium <i>tert</i>-butylate; hydrogen In cyclohexane at 100℃; for 16h; Inert atmosphere; Autoclave;
  • 63
  • [ 145235-81-0 ]
  • [ 62-53-3 ]
  • [ 621-06-7 ]
YieldReaction ConditionsOperation in experiment
89% With tris(2,2'-bipyridyl)ruthenium dichloride In acetonitrile at 20℃; Irradiation;
  • 64
  • [ 103-82-2 ]
  • N-tert-butyl-N'-phenyl-S-phenylisothiourea [ No CAS ]
  • [ 621-06-7 ]
YieldReaction ConditionsOperation in experiment
98% With iron(III)-acetylacetonate In isopropyl alcohol at 83℃; for 24h; Microwave irradiation;
  • 65
  • [ 621-06-7 ]
  • [ 98-95-3 ]
  • [ 33142-36-8 ]
YieldReaction ConditionsOperation in experiment
56% With potassium <i>tert</i>-butylate In dimethyl sulfoxide at 20℃; for 4h; Inert atmosphere; chemoselective reaction;
  • 66
  • [ 7270-63-5 ]
  • [ 621-06-7 ]
  • C16H13NO2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
68% With bis[dichloro(pentamethylcyclopentadienyl)iridium(III)]; sodium acetate; silver(I) triflimide In 1,4-dioxane at 70℃; for 10h;
  • 67
  • [ 260783-80-0 ]
  • [ 201230-82-2 ]
  • [ 62-53-3 ]
  • [ 621-06-7 ]
YieldReaction ConditionsOperation in experiment
97% With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate; triphenylphosphine In dimethyl sulfoxide; toluene at 100℃; for 12h; Schlenk technique;
95% With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate; triphenylphosphine In dimethyl sulfoxide; toluene at 100℃; Schlenk technique; 1 To a dried Schlenk tube was added stirring, PdCl2(dppf)(4.4mg,0.006mmol),PPh3(15.7mg, 0.06mmol), Na2CO3(42.4mg, 0.4mmol), trimethyl benzyl ammonium triflate (0.4 mmol), a CO-filled balloon was attached to a Schlenk tube, and then pumped by the air pump system, purified three times; Schlenk tube filled with the entire atmosphere of CO.1mL PhMe and then injected into a micro-syringe injection 0.2mL DMSO and then 0.2mmol of aniline by syringe.The reaction was at 100 for reaction, TLC monitoring of the reaction was followed until the reaction was complete aniline, reaction was removed, cooled to room temperature.Was added to the reaction mixture 4mL of saturated sodium chloride solution, extracted with ethyl acetate (3 × 10mL), the organic phases were combined and dried over anhydrous sodium sulfate, filtered, and rotary evaporated to give the crude product is spin-dried, and finally the column layer Analysis of separation and purification to give pure amide product.As a pale yellow solid, yield 95%.
  • 68
  • [ 2009-97-4 ]
  • [ 621-06-7 ]
  • ethyl 2-methyl-1-(2-phenylacetyl)-1H-indole-3-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
63% With bis[dichloro(pentamethylcyclopentadienyl)iridium(III)]; acetic acid; silver(I) triflimide In 1,2-dichloro-ethane at 60℃; for 10h;
  • 69
  • [ 140-29-4 ]
  • [ 114-83-0 ]
  • [ 38604-74-9 ]
  • [ 621-06-7 ]
YieldReaction ConditionsOperation in experiment
1: 72% 2: 19% With bis-[(trifluoroacetoxy)iodo]benzene In neat (no solvent) at 40℃; for 2h; Sealed tube;
  • 70
  • [ 1197040-29-1 ]
  • [ 1666-17-7 ]
  • [ 621-06-7 ]
YieldReaction ConditionsOperation in experiment
60% With water; palladium diacetate; triphenylphosphine; lithium tert-butoxide In tetrahydrofuran at 100℃; for 5h; Sealed tube;
  • 71
  • [ 621-06-7 ]
  • [ 7338-94-5 ]
  • [ 131684-06-5 ]
YieldReaction ConditionsOperation in experiment
30% With potassium hydroxide In 1,4-dioxane at 100℃; for 6h; Sealed tube; Green chemistry;
  • 72
  • [ 108-88-3 ]
  • [ 103-70-8 ]
  • [ 621-06-7 ]
YieldReaction ConditionsOperation in experiment
56% With bis(acetylacetonate)nickel(II); di-tert-butyl peroxide; carbon monoxide at 110℃; for 16h; Autoclave; (1) Typical procedure for the reaction of alkanes (1) and formanilides (2) without auxiliary solvent General procedure: To a 50 mL of autoclave, was added cyclohexane (1a, 20 mL),formanilide (2a, 10 mmol), Ni(acac)2 (1 mmol, 0.26 g) and DTBP(12 mmol, 1.76 g). After replaced with argon twice, the autoclave was rinsed three times with CO and then heated to 110°C under 20 bar CO for 16 h. The autoclave is then cooled to room temperature and carefully relieved of pressure. The solid catalyst was filtered off. The excess alkane was removed under reduced pressureand the residue was separated by silica gel column chromatography (Petroleum ether/ethyl acetate) to give the product 3aa.
  • 73
  • [ 621-06-7 ]
  • N-(4-hydroxy-2-nitrophenyl)-2-phenylacetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
49% With boron trifluoride diethyl etherate; nitric acid; acetic acid; bis-[(trifluoroacetoxy)iodo]benzene In water at 80℃; for 2.5h;
  • 74
  • [ 621-06-7 ]
  • [ 64-19-7 ]
  • 3-nitro-4-(2-phenylacetamido)phenyl acetate [ No CAS ]
YieldReaction ConditionsOperation in experiment
52% With boron trifluoride diethyl etherate; nitric acid; bis-[(trifluoroacetoxy)iodo]benzene In water at 40℃; for 1.5h;
  • 75
  • S-phenylacetyl-5,6-diphenyl-1,2,4-triazine-3-thione [ No CAS ]
  • [ 62-53-3 ]
  • [ 621-06-7 ]
YieldReaction ConditionsOperation in experiment
85% In chloroform at 20℃; Aminolysis of N-PaDTT (3′) with amines (8) :formation of amides (18) N-PaDTT (3′, 0.268g, 2 mmol) in chloroform (10ml) was mixed up with freshly distilled aniline (8a, 0.2ml, 2 mmol). The reaction mixture was stirred for 5min under the room temp conditions. During the courseof reaction, the dark green colour changed to redorange indicating the regeneration of 3-mercapto-5,6-diphenyl-1,2,4-triazine (1). The products wereseparated using alumina column. The first fraction wasidentified as phenyl acetyl aminobenzene (18a) yield0.31g (85%), m.p. 117 0 (lit 23 118 0 ). 3-Mercapto-5,6-diphenyl-1,2,4-triazine (1) was also separated as byproduct in almost quantitative yield.To verify the generality of the above reaction,aminolysis was extended to other amines like 2-methylaniline (8b), 4-methylaniline (8d), benzyl amine(8g), ethyl amine (8j). The respective amides, phenylacetyl amino (2-methyl) benzene (18b), phenyl acetylamino (4-methyl) benzene (18d), N-Benzoyl-2-phenylethanamide (18g), phenyl acetylamino ethane(18j), were obtained in 70-80% yield. The reactionswere also followed by tlc and spectrophotometrically.Using neutral alumina column all the products wereseparated and characterized. The characterizationdata are given in Table-1. In all aminolysis reactions3-mercapto-5,6-diphenyl-1,2,4-triazine (1) was isolatedalmost in quantitative yield.
  • 76
  • [ 98-95-3 ]
  • [ 101-97-3 ]
  • [ 621-06-7 ]
YieldReaction ConditionsOperation in experiment
81% Stage #1: nitrobenzene; Ethyl 2-phenylethanoate With chromium chloride; chloro-trimethyl-silane; magnesium; 4,4'-di-tert-butyl-2,2'-bipyridine In tetrahydrofuran at 90℃; for 12h; Schlenk technique; Inert atmosphere; Stage #2: With hydrogenchloride; water In tetrahydrofuran
  • 77
  • [ 103-82-2 ]
  • [ 100-46-9 ]
  • [ 621-06-7 ]
YieldReaction ConditionsOperation in experiment
75% With polystyrene-supported boronic acid In toluene at 160 - 165℃; for 24h; Dean-Stark;
  • 78
  • [ 26306-06-9 ]
  • [ 621-06-7 ]
YieldReaction ConditionsOperation in experiment
87% With phthalic anhydride; zinc trifluoromethanesulfonate In acetonitrile at 20℃; Inert atmosphere; 3. General procedure for o-phthalic anhydride/Zn(OTf)2 co-catalyzed Beckmann rearrangement General procedure: Oxime 1 (1.0 mmol, 1.0 equiv), Zn(OTf)2 (73.7 mg, 0.2 mmol, 0.2 equiv) and o-phthalic anhydride (15.0 mg, 0.1 mmol, 0.1 equiv) were dissolved in 1.0 mL CH3CN at rt under nitrogen atomesphere and stirred until the complete consumption of the oxime monitored by TLC analysis. The mixture was evaporated and the residue was purified on flash column chromatography with petroleum ether/ethyl acetate (5:1~2:1) as eluent to afford the desired amide 2.
84% With 1,1,1,3',3',3'-hexafluoro-propanol; tetrabutylammonium tetrafluoroborate; water In 1,2-dichloro-ethane at 20℃; for 0.733333h; Electrochemical reaction;
  • 79
  • [ 621-06-7 ]
  • [ 7495-11-6 ]
YieldReaction ConditionsOperation in experiment
86% With tetrabutylammomium bromide; copper(ll) bromide In tetrahydrofuran at 65℃; regioselective reaction; General procedure for the synthesis of 1b-14ba, 15b-44b General procedure: A round bottom flask was charged with Bu4NBr (2 mmol, 0.64 g), EtOH (8 mL) and 2-methylaniline (2 mmol, 0.21 g) followed by CuBr2 (3 mmol, 0.67 g). The resulted mixture was stirred at 25 °C. After the completion of the reaction (monitored by TLC), the solvent was evaporated under reduced pressure. To the residue was added ammonium hydroxide (5 mL, 25% w/v) and water (5 mL) with stirring, and the suspension was extracted with DCM(10 mL×4) The organic phase was washed with saturated brine and dried over anhydrous Na2SO4. The product 2b was obtained using flash chromatograph column eluted with PE : EA (5 : 1).
  • 80
  • [ 59-88-1 ]
  • [ 140-29-4 ]
  • [ 621-06-7 ]
YieldReaction ConditionsOperation in experiment
65% With tert.-butylnitrite; iodine In neat (no solvent) at 25℃; for 6h; II. Typical Experimental Procedure For 3 (3a as an example): General procedure: To a round-bottom flask (25 mL) was added phenylhydrazine hydrochloride 1a (43 mg, 0.3 mmol), benzonitrile 2a (0.3 mL, 3 mmol), t-BuONO (53 μL, 0.45 mmol), I2 (38 mg, 0.15 mmol), the mixture was well stirred for 6 h at 25 oC (the whole process was closely monitored by TLC). Then the reaction mixture was purified by a flash silica gel column chromatography (eluent: Petroleum ether (PE)/Ethyl acetate (EA) = 10:1) to give N-phenylbenzamide 3a as a white solid (38 mg, 64%).
  • 81
  • [ 536-74-3 ]
  • [ 62-53-3 ]
  • [ 621-06-7 ]
YieldReaction ConditionsOperation in experiment
98% With potassium hexafluorophosphate; 4-methylpyridine-1-oxide; chloro(cyclopentadienyl)bis(triphenylphosphine)ruthenium (II) In water; 1,2-dichloro-ethane at 100℃; for 24h; Inert atmosphere; Sealed tube;
  • 82
  • [ 4472-41-7 ]
  • [ 621-06-7 ]
  • C15H12(2)HNO [ No CAS ]
YieldReaction ConditionsOperation in experiment
69% With dimethylamine borane; potassium <i>tert</i>-butylate at 120℃; for 0.5h; Inert atmosphere;
  • 83
  • [ 62167-00-4 ]
  • [ 62-53-3 ]
  • [ 621-06-7 ]
YieldReaction ConditionsOperation in experiment
78% With 10-methyl-9-(2,4,6-trimethylphenyl) acridinium tetrafluoroborate In acetonitrile at 20℃; for 5h; Irradiation;
78% With 10-methyl-9-(2,4,6-trimethylphenyl) acridinium tetrafluoroborate In acetonitrile at 20℃; for 5h; Irradiation; 16 Example 16: Preparation of N, 2-diphenylacetamide (3p) Under air, aniline (0.2 mmol, 19 mg) was dissolved in acetonitrile (2 mL), and Mes-Acr-MeBF4 (2 mol%, 2 mg) and thiophenylacetic acid (0.4 mmol, 61 mg) were added. The mixture was stirred under 36W blue LED at room temperature for 5 hours. The mixture was quenched with water (2 mL) and then extracted with EtOAc (3 x 4 mL). The organic phase was washed with brine, dried over Na 2 SO 4 and spin-dried, and then separated by column chromatography to obtain 33 mg of a white solid product with a yield of 78%.
  • 84
  • (±)-cis-phenyloxirane-2-carbonitrile [ No CAS ]
  • [ 62-53-3 ]
  • [ 621-06-7 ]
YieldReaction ConditionsOperation in experiment
66% With boron trifluoride diethyl etherate In 1,4-dioxane at 190℃; for 0.5h; Microwave irradiation; Green chemistry;
  • 85
  • [ 40669-47-4 ]
  • [ 621-06-7 ]
YieldReaction ConditionsOperation in experiment
57% With methanol; copper acetylacetonate; water; N-fluorobis(benzenesulfon)imide In acetonitrile at 80℃; for 24h; Schlenk technique; Inert atmosphere;
  • 86
  • [ 103-81-1 ]
  • [ 108-90-7 ]
  • [ 621-06-7 ]
YieldReaction ConditionsOperation in experiment
With C33H37N4P; potassium carbonate; bis(dibenzylideneacetone)-palladium(0) In <i>tert</i>-butyl alcohol at 95℃; for 5h; Inert atmosphere; Sonication; 14 Example 14 Under the protection of nitrogen, add 1mol% Pd (dba) 2 (7.96mg) and 2mol% ligand [IV] (16.00mg) to the 25mL reaction tube with branch tube.Add phenylacetamide (0.36g, 1.2 equivalent) and potassium carbonate (0.46g, 1.5 equivalent),Replace the air with nitrogen three times, then add ultrasonic deoxygenated tert-butanol (2.5g) and replace with nitrogen,Then add chlorobenzene (0.25g, 1.0 equivalent), replace with nitrogen three times, increase the temperature to 95 ° C, react for 5h, and detect by gas phase, the conversion rate is 99.3%.
With C33H37N4P; potassium carbonate; bis(dibenzylideneacetone)-palladium(0) In <i>tert</i>-butyl alcohol at 95℃; for 5h; Inert atmosphere; Sonication; 14 Example 14 Under the protection of nitrogen, add 1mol% Pd (dba) 2 (7.96mg), 2mol% ligand [] (16.00mg) into a 25mL reaction tube with branch tube, and then add phenylacetamide (0.36g, 1.2 equivalent) and Potassium carbonate (0.46g, 1.5 equiv), replace air with nitrogen three times, then add ultrasonic deoxygenated tert-butanol (2.5g) and replace with nitrogen, then add chlorobenzene (0.25g, 1.0 equiv), replace with nitrogen three times, heat up To 95 , reaction 5h, gas phase detection, conversion rate 99.3%
  • 87
  • [ 621-06-7 ]
  • [ 96746-54-2 ]
YieldReaction ConditionsOperation in experiment
85% With picoline; diphenyl phosphoryl azide for 16h; Reflux; Inert atmosphere;
85% With diphenyl phosphoryl azide for 16h; Reflux; Inert atmosphere; Synthesis of 1,5-disubstituted tetrazoles General procedure: DPPA or p-NO2DPPA (0.4mmol) was added to a solution containing the amide (0.2mmol) in pyridine or 4-methylpyridine (0.3mL) under an N2 atmosphere. After stirring for 16h at reflux (oil bath), the mixture was diluted with AcOEt (30mL). The mixture was washed with 1N HCl, water, saturated aqueous NaHCO3, and brine (25mL), and then dried over Na2SO4. Concentrating the solvent in vacuo followed by purification of the residue on a silica gel column (AcOEt:n-Hexane 1:1-1:4) gave the desired tetrazole.
  • 88
  • [ 2990-05-8 ]
  • [ 621-06-7 ]
YieldReaction ConditionsOperation in experiment
85% With 1-[2-(N-(3-diphenylphosphinopropyl))aminoethyl]pyrrolidine; triethylamine; palladium dichloride In water at 100℃; for 12h; regioselective reaction; General Procedure for Hydrodehalogenation of o-Haloanilides General procedure: To a stirred solution of o-haloanilide (1 mmol), PdCl2 (3.6 mg,0.02 mmol), Et3N (202 mg, 2 mmol), and dppap (8.5 mg, 0.05mmol) in water (5 mL) at 100 °C for 12 h. After completion ofthe reaction (indicated by TLC), the mixture was filtered, andthe filtrate was extracted with EtOAc (2 × 5 mL). The organiclayer was dried by anhydrous Na2SO4, concentrated in vacuo,and the residue was isolated by column chromatography(PE/EtOAc, 5:1) to afford the respective products.
  • 89
  • [ 13140-72-2 ]
  • [ 621-06-7 ]
YieldReaction ConditionsOperation in experiment
84% With 1-[2-(N-(3-diphenylphosphinopropyl))aminoethyl]pyrrolidine; triethylamine; palladium dichloride In water at 100℃; for 12h; regioselective reaction; General Procedure for Hydrodehalogenation of o-Haloanilides General procedure: To a stirred solution of o-haloanilide (1 mmol), PdCl2 (3.6 mg,0.02 mmol), Et3N (202 mg, 2 mmol), and dppap (8.5 mg, 0.05mmol) in water (5 mL) at 100 °C for 12 h. After completion ofthe reaction (indicated by TLC), the mixture was filtered, andthe filtrate was extracted with EtOAc (2 × 5 mL). The organiclayer was dried by anhydrous Na2SO4, concentrated in vacuo,and the residue was isolated by column chromatography(PE/EtOAc, 5:1) to afford the respective products.
82% With copper acetylacetonate; diethylamine; vasicine In ethanol at 100℃; for 12h; Sealed tube; 3 Add 1b (1mmol, 289mg), copper acetylacetonate (0.2mmol, 52mg), anatine (0.4mmol, 76mg), diethylamine (2mmol, 146mg) and ethanol (5mL) to a 10mL reaction tube. The reaction tube was sealed and placed in an oil bath at 100° C. and stirred for 12 hours, and then cooled to room temperature. After concentration in vacuo and separation by column chromatography, the target product 2b (173 mg, 82%) was obtained.
81% With copper acetylacetonate; ethanol; diethylamine; vasicine at 100℃; for 12h; Sealed tube; regioselective reaction; 1.3 General procedure for the hydrodehalogenation of o-haloanilides General procedure: To a stirred solution of the 2-bromoanilide 1xa or 2-iodmoanilide 1xb (1 mmol), Cu(acac)2 (13mg, 0.05 mmol), vasicine (19 mg, 0.1 mmol) and Et2NH (146 mg, 2 mmol), EtOH (5 mL) in a sealed tube at 100 °C for 12 h. After cooled to room temperature, the reaction was concentrated in vacuo and purified by column chromatography to afford respective products.
  • 90
  • [ 201230-82-2 ]
  • [ 100-44-7 ]
  • [ 62-53-3 ]
  • [ 621-06-7 ]
YieldReaction ConditionsOperation in experiment
85% With palladium diacetate; N-ethyl-N,N-diisopropylamine; bis[2-(diphenylphosphino)phenyl] ether In toluene at 70℃; for 16h; Inert atmosphere; General Procedure General procedure: To a round-bottomed ACE glass pressureflask containing a magnetic stirrer was added toluene (20 mL),chloromethylbenzene (1.0 g, 7.9 mmol) and N,N-diisopropylethylamine(1.5 equiv). The mixture was degassed with subsurfacenitrogen purge for 5 minutes. Palladium(II) acetate (2.5mol%) and bis(2-diphenylphosphinophenyl)ether (5 mol%)were added, followed by the primary or secondary amine (1.2equiv) to give a pale-yellow solution. The flask was purged withnitrogen, filled with carbon monoxide to 50 psig and heated at70 °C with magnetic stirring overnight. The reaction mixturewas cooled to ambient temperature and residual CO vented. Thereaction mixture was partitioned between EtOAc (200 mL) and10% aq. citric acid (2 × 30 mL). The organic layer was washedwith water then brine, dried over MgSO4, filtered and evaporated.The residue was loaded to the top of a silica gel plug withCH2Cl2 and eluted with a gradient of EtOAc in isohexane toafford the amide products.
  • 91
  • [ 329937-74-8 ]
  • [ 621-06-7 ]
YieldReaction ConditionsOperation in experiment
85% With copper acetylacetonate; diethylamine; vasicine In ethanol at 100℃; for 12h; Sealed tube; 4 Add 1b' (1mmol, 337mg), copper acetylacetonate (0.05mmol, 13mg), anatine (0.1mmol, 19mg), diethylamine (2mmol, 146mg) and ethanol (5mL) to a 10mL reaction tube. The reaction tube was sealed and placed in an oil bath at 100° C. and stirred for 12 hours, and then cooled to room temperature. Concentrated in vacuo and separated by column chromatography to obtain the target product 2b (179 mg, 85%).
85% With copper acetylacetonate; ethanol; diethylamine; vasicine at 100℃; for 12h; Sealed tube; regioselective reaction; 1.3 General procedure for the hydrodehalogenation of o-haloanilides General procedure: To a stirred solution of the 2-bromoanilide 1xa or 2-iodmoanilide 1xb (1 mmol), Cu(acac)2 (13mg, 0.05 mmol), vasicine (19 mg, 0.1 mmol) and Et2NH (146 mg, 2 mmol), EtOH (5 mL) in a sealed tube at 100 °C for 12 h. After cooled to room temperature, the reaction was concentrated in vacuo and purified by column chromatography to afford respective products.
  • 92
  • [ 62-53-3 ]
  • [ 620-05-3 ]
  • [ 199620-15-0 ]
  • [ 621-06-7 ]
YieldReaction ConditionsOperation in experiment
90% In N,N-dimethyl-formamide at 25℃; for 48h; Irradiation; Green chemistry;
Same Skeleton Products
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