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Chemical Structure| 588-46-5 Chemical Structure| 588-46-5
Chemical Structure| 588-46-5

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Product Details of N-Benzylacetamide

CAS No. :588-46-5
Formula : C9H11NO
M.W : 149.19
SMILES Code : CC(NCC1=CC=CC=C1)=O
English Name :N-Benzylacetamide
MDL No. :MFCD00059204
InChI Key :UZJLYRRDVFWSGA-UHFFFAOYSA-N
Pubchem ID :11500

Safety of N-Benzylacetamide

Application In Synthesis of N-Benzylacetamide

* 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 [ 588-46-5 ]

[ 588-46-5 ] Synthesis Path-Downstream   1~20

  • 1
  • [ 588-46-5 ]
  • [ 56222-10-7 ]
YieldReaction ConditionsOperation in experiment
54% With sulfuric acid; nitric acid at 10 - 15℃;
With nitric acid
nitration;
  • 3
  • [ 1432-43-5 ]
  • [ CAS Unavailable ]
  • [ 588-46-5 ]
YieldReaction ConditionsOperation in experiment
19% In acetonitrile for 3h; Ambient temperature;
  • 4
  • [ 588-46-5 ]
  • [ 34185-04-1 ]
  • [ 80311-94-0 ]
YieldReaction ConditionsOperation in experiment
1: 12% 2: 2% With potassium superoxide; 18-crown-6 ether In benzene for 168h; Ambient temperature; aromatic ortho and para hydroxylation of various N-benzylamides with potassium superoxide;
1: 2% 2: 12% With potassium superoxide; 18-crown-6 ether In benzene for 168h; Ambient temperature;
  • 5
  • [ CAS Unavailable ]
  • [ 4626-58-8 ]
  • [ 1575-46-8 ]
  • [ 588-46-5 ]
  • [ 78075-81-7 ]
  • [ 96240-08-3 ]
YieldReaction ConditionsOperation in experiment
1: 35% 2: 10% With rhodium(II) acetate; hydrogen; triphenylphosphine In ethyl acetate at 90℃; for 20h;
  • 6
  • [ 5817-70-9 ]
  • [ 75-36-5 ]
  • [ 588-46-5 ]
YieldReaction ConditionsOperation in experiment
65% With sodium iodide In acetonitrile at 60℃; for 15h;
  • 7
  • [ 13031-43-1 ]
  • [ 100-46-9 ]
  • [ 588-46-5 ]
  • 8
  • [ 588-46-5 ]
  • [ 7697-37-2 ]
  • [ 180080-55-1 ]
  • [ 56222-10-7 ]
YieldReaction ConditionsOperation in experiment
at 0℃; Nitrierung;
  • 9
  • [ 5817-70-9 ]
  • [ 75-24-1 ]
  • [ 588-46-5 ]
YieldReaction ConditionsOperation in experiment
67% In 1,2-dichloro-ethane; toluene at -30 - 65℃; for 48h;
  • 10
  • [ 588-46-5 ]
  • [ 133816-00-9 ]
  • [ 887266-68-4 ]
YieldReaction ConditionsOperation in experiment
33% With potassium hexamethylsilazane In toluene at -30 - 20℃; for 15h;
Stage #1: N-(phenylmethyl)acetamide With potassium hexamethylsilazane In toluene at -30 - 20℃; Stage #2: phenyl(trimethylsilylethynyl)iodonium triflate In toluene at 20℃; for 15h;
With potassium hexamethylsilazane In toluene at 20℃;
  • 11
  • [ 588-46-5 ]
  • [ 2015-14-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: chlorosulfuric acid 2: aqueous ammonia
  • 12
  • [ 111-35-3 ]
  • [ 100-46-9 ]
  • [ 588-46-5 ]
  • [ 10264-12-7 ]
YieldReaction ConditionsOperation in experiment
1: 75% 2: 71% With dichloro(benzene)ruthenium(II) dimer; N,N-diisopropylimidazolium bromide; sodium hydride In toluene; acetonitrile at 115℃; for 24h; Inert atmosphere; Reflux;
  • 13
  • [ 334-88-3 ]
  • [ 124-38-9 ]
  • [ 1594106-07-6 ]
  • [ 588-46-5 ]
  • [ 10479-30-8 ]
  • [ 96011-42-6 ]
YieldReaction ConditionsOperation in experiment
1: 51 %Spectr. 2: 15 %Spectr. 3: 13 %Spectr. Stage #1: carbon dioxide; N-benzyl-N-(methoxy(phenyl)methyl)acetamide With aluminum (III) chloride; manganese; lithium chloride In tetrahydrofuran at 60℃; for 18h; Stage #2: diazomethane In tetrahydrofuran
1: 45 %Spectr. 2: 22 %Spectr. 3: 7 %Spectr. Stage #1: carbon dioxide; N-benzyl-N-(methoxy(phenyl)methyl)acetamide With manganese; boron trifluoride diethyl etherate; lithium chloride In tetrahydrofuran at -10℃; for 18h; Stage #2: diazomethane In tetrahydrofuran
1: 67 %Spectr. 2: 8 %Spectr. 3: 7 %Spectr. Stage #1: carbon dioxide; N-benzyl-N-(methoxy(phenyl)methyl)acetamide With manganese; boron trifluoride diethyl etherate; lithium chloride In tetrahydrofuran at 0℃; for 18h; Stage #2: diazomethane In tetrahydrofuran
  • 14
  • [ 334-88-3 ]
  • [ 124-38-9 ]
  • [ 1594106-07-6 ]
  • [ 588-46-5 ]
  • [ 10479-30-8 ]
YieldReaction ConditionsOperation in experiment
1: 44 %Spectr. 2: 9 %Spectr. Stage #1: carbon dioxide; N-benzyl-N-(methoxy(phenyl)methyl)acetamide With aluminum (III) chloride; magnesium In tetrahydrofuran at 60℃; for 18h; Stage #2: diazomethane In tetrahydrofuran
  • 15
  • [ 588-46-5 ]
  • [ 28073-51-0 ]
  • [ 88963-85-3 ]
YieldReaction ConditionsOperation in experiment
With chlorosulfonic acid at 50 - 75℃; for 3.5h; Overall yield = 67 %; Overall yield = 467 mg; Intermediate 34 - 4-(N-methylacetamido)benzenesulfonyl chloride N-methylacetanilide (500 mg, 3.35 mmol) was placed in an ice bath with stirring, and 2 ml of chlorosulfonic acid (used as a solvent) was slowly added dropwise after cooling. After the completion of the dropwise addition, the mixture was slowly warmed to room temperature for 10 minutes, placed in a 50 ° C oil bath for 1.5 hours, and further raised to 75 ° C for 2 hours. After adding ice cubes to quench the reaction, the mixture was extracted three times with ethyl acetate, and the organic phase was combined and washed three times with saturated brine. Drying with anhydrous magnesium sulfate, filtration, distillation under reduced pressure, Purification by column chromatography to give intermediate 34 (light grey solid 539mg), The yield was 65%.Show moreShow less
  • 16
  • [ 100-46-9 ]
  • [ 562-90-3 ]
  • [ 588-46-5 ]
YieldReaction ConditionsOperation in experiment
99% In tetrahydrofuran at 20℃; for 0.5h;
  • 17
  • [ 574-39-0 ]
  • [ 100-46-9 ]
  • [ 588-46-5 ]
YieldReaction ConditionsOperation in experiment
99% In tetrahydrofuran at 30℃; for 24h; The General Procedure of N-Acylation in Scheme 3,4, and 6. General procedure: To a solution of NAC 1a or 1b12 (0.3mmol) in THF(0.5 M) was added amine (0.9mmol) at 30 °C. The mixture was stirred for 24 h, quenched with 1N HCl, and extracted with EtOAc (3). The combined organic layers were washed with brine, dried over anhydrous MgSO4, and filtered. The filtrate was concentrated under reduced pressure. The residue was purified by column chromatography on silica gel to give the corresponding N-Bz or N-Ac amides 3.
  • 18
  • [ 14897-48-4 ]
  • [ 5122-20-3 ]
  • [ 588-46-5 ]
  • [ 2410292-47-4 ]
YieldReaction ConditionsOperation in experiment
1: 6.04 g 2: 4.1 g With benzylamine; copper(I) bromide at 110℃; for 6h; Inert atmosphere; Sealed tube; 4.3.12.2. Isolation of the N-benzyl acetamide co-product. 4.3.12.1 Gravimetric determination of the aryl iodide conversion Using 1/3 amounts of reagents and same conditions as above but heating the reaction mixture only for 6 h at 110 °C resulted in ∼80 % conversion of aryl iodide (30 mmol), the limiting reagent. This figure was calculated by gravimetric analysis of the water soluble iodide ions in the form of CuI precipitate. For this reason the steam distillation residue of the boiler flask was first extracted with ether to remove the co-product N-benzyl acetamide and the residual free benzyl amine. Next the water layer was filtered to remove the remains of the copper(I) catalyst (5 mol %) used. Note that CuBr was transformed to CuI in the reaction due to its higher stability and lower solubility in the amine solvents and water. The clear filtrate was treated with CuSO4×5H2O (35 mmol) and the liberated I2 was titrated with NaHSO3 solution. The precipitated CuI was filtered, triturated with methanol, filtered again and washed with 20 % HCl and water, and dried to give 4.6 g (24 mmol) of CuI as cream-white powder. Working up the steam distillate of this experiment as shown in subsection 4.3.12 gave 6.04 g (73 %) 11l sulfide as a colorless oil of bp 142-143 °C/16 mmHg, containing ∼15 mol% unreacted 10l aryl iodide as determined by 1H NMR analysis. This result suggests that the sulfide 11l and its precursor iodide 10l should have similar boiling points, thus they are difficult to separate by distillation. Instead, longer reaction time or the use of a larger excess of the CF3CH2SH source could result in the complete conversion of this sterically hindered aryl iodide and will allow simple isolation of the pure product by distillation. 4.3.12.2 Isolation of the N-benzyl acetamide co-product The ether extract of the experiment in subsection 4.3.12.1 was washed with 5 % HCl and water, then dried (Na2SO4). Evaporation of the solvent afforded slightly brown crystalline product, which was identified by 1H and 13C NMR as CH3CONHCH2C6H5. Yield: 4.10 g (27.5 mmol, 92 % referred to the 30 mmol of trifluoroethyl thioacetate 9 used). (0043) 1H NMR (250 MHz, CDCl3) δ 7.40 - 7.15 (m, 5H, Ar), 6.28 (br s, 1H, NH), 4.38 (d, 3JHH = 5.7 Hz, 2H, CH2), 1.97 (s, 3H, CH3); 13C NMR (63 MHz, CDCl3) δ 170.6 (CO), 138.6 (Ar), 129.1 (Ar), 128.2 (Ar), 127.9 (Ar), 44.1 (CH3), 23.5 (CH2).
  • 19
  • [ 588-46-5 ]
  • [ 85690-51-3 ]
  • [ 99362-10-4 ]
  • [ 180080-56-2 ]
YieldReaction ConditionsOperation in experiment
Stage #1: N-(phenylmethyl)acetamide With 1,1,1,3',3',3'-hexafluoro-propanol; 2-tert-butyl-1,1,3,3-tetramethylguanidine; 5-(trifluoromethyl)picolinic acid at -18℃; Inert atmosphere; Sealed tube; Stage #2: With hydroxylamine-O-sulfonic acid at 30℃; Inert atmosphere; Sealed tube; Overall yield = 52 percent;
  • 20
  • [ 588-46-5 ]
  • [ 1640981-20-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: pyridine; trifluoromethylsulfonic anhydride / dichloromethane / 2 h / 0 - 25 °C / Inert atmosphere 1.2: 3 h / 18 - 25 °C / Inert atmosphere 2.1: N-Bromosuccinimide / acetonitrile / 2 h / 0 - 25 °C 3.1: 6-hydroxy-N-(4-hydroxy-2,6-dimethylphenyl)picolinamide; copper(l) iodide; potassium phosphate; water / dimethyl sulfoxide / 31.5 h / 80 °C / Inert atmosphere
 

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