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Product Details of [ 2707-23-5 ]

CAS No. :2707-23-5 MDL No. :MFCD00084933
Formula : C9H7ClF3NO Boiling Point : -
Linear Structure Formula :- InChI Key :BHXKHTOSJBCCMU-UHFFFAOYSA-N
M.W : 237.61 Pubchem ID :2736464
Synonyms :

Safety of [ 2707-23-5 ]

Signal Word:Danger Class:8
Precautionary Statements:P260-P264-P270-P280-P301+P330+P331-P303+P361+P353-P304+P340-P305+P351+P338-P310-P363-P405-P501 UN#:3261
Hazard Statements:H302-H314 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 2707-23-5 ]

* 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 [ 2707-23-5 ]

[ 2707-23-5 ] Synthesis Path-Downstream   1~5

  • 1
  • [ 455-14-1 ]
  • [ 79-04-9 ]
  • [ 2707-23-5 ]
YieldReaction ConditionsOperation in experiment
97% With Sodium hydrogenocarbonate In dichloromethane at 0 - 20℃; for 4h;
97% With Sodium hydrogenocarbonate In dichloromethane at 0℃; for 4h;
96% With Sodium hydrogenocarbonate In dichloromethane at 0℃; for 1h; 5 General synthetic procedure for the intermediates 4a-4s General procedure: Propionyl chloride (6.0mmol) in dry CH2Cl2 (10mL) was added dropwise to a mixture of 4-methoxybenzenamine (5.0mmol), sodium bicarbonate (12.5mmol) and dry CH2Cl2 (15mL). The mixture was stirred in ice water bath for 1h and poured into water and then extracted with CH2Cl2 (3×30mL). The combined organic layer was washed with brine and dried over anhydrous MgSO4. The solvent was evaporated to dryness to afford the compound 4a. Others amide derivatives 4b-4s were synthesized similarly. Physical constants and spectral data of compounds 4a-4s are summarized below.
92.2% With potassium carbonate In acetone at 0 - 15℃;
88.5% With triethylamine In dichloromethane at 0 - 25℃;
88.5% With triethylamine In dichloromethane at 0 - 25℃; 5.2.1. General procedure for synthesis of 2-chloro-N-substituted-acetamide (1a-v) General procedure: 2-Chloroacetyl chloride (24 mmol) was slowly added dropwise to a mixture of R-NH2 (20 mmol) and Et3N (24 mmol, 3.3 mL) in anhydrous CH2Cl2 (20 mL) at 0 °C. The reaction mixture was warmed to room temperature and stirred for an additional 20 h. After the solvent was removed under reduced pressure, the residue was washed with ice water (3 × 20 mL) and the precipitate was separated by filtration. The crude product was purified by crystallization from a mixture solvent of Et2O/petroleum.
88% In N,N-dimethyl acetamide at 0 - 20℃;
84% With anhydrous Sodium acetate In glacial acetic acid for 0.5h; Cooling with ice; 4.1.1 General synthetic procedure for 2-chloro-N-(substituted) phenyl acetamides (12a-o) General procedure: Initially, appropriate amine (0.05mol) was dissolved in glacial acetic acid (25ml) containing saturated solution of sodium acetate (25ml). In case, if the substance did not dissolve completely then the mixture was warmed and the resultant solution was cooled in an ice-bath with stirring. To the ice cold solution chloroacetyl chloride (4.8ml, 0.06mol) was added drop wise with continuous stirring to avoid the vigorous reaction. After half an hour, a white colored product was separated out and filtered. The product was firstly washed with 50% aqueous acetic acid and finally with water. The crude product was then recrystallized from ethanol. The product so obtained was dried under vacuum to obtain the series of intermediate compounds (12a-o).
80% With triethylamine In dichloromethane at 0 - 20℃; for 1h; 2-Chloro-N-(3-(trifluoromethoxy)phenyl)acetamide General procedure: To a stirred solution of3-(trifluoromethoxy)aniline (1.85 mL, 13.81 mmol) in dichloromethane (40 mL)was added chloroacetyl chloride (1.42 g, 12.56 mmol) at 0 oC.The reaction mixture was stirred at room temperature for 1 h. Diluteddichloromethane (40 mL), the mixture was washed with 2N HCl (40 mL), brine (40mL) and water (40 mL). The organic layer was dried over MgSO4,filtered and concentrated to get the crude residue, which was purified bysilica gel column chromatography (EtOAc/Hx = 2/8) to give 2-chloro-N-(3-(trifluoromethoxy)-phenyl)acetamide(2.5 g, 79%) as a white solid.
80% With triethylamine In dichloromethane at 0 - 20℃; for 1h; 3) synthesis of Substance 2 Substance 2-1 (5 mL, 39.82 mmol) was dissolved in dichloromethane (250 mL) and triethylamine (8.32 mL, 59.72 mmol) was added.After addition, chloroacetyl chloride (3.48 mL, 43.80 mmol) was slowly added dropwise at 0°C. After the reaction mixture is stirred at room temperature for 1 hour, when the reaction is completed, dichloromethane is added to dilute the solution and washed with 2N HCl and water. After the organic layers were collected, magnesium sulfate was added, filtered, and the filtrate was concentrated to obtain material 2 (7.62 g, 80%) by silica gel chromatography (eluent ethyl acetate:hexane = 1:4).
78% With pyridine In dichloromethane at 20℃; for 12h; 1.1
General procedure for the synthesis of 2-halo-N-arylacetamides (2a-2i) General procedure: The solution of arylamine (1.0 equiv.) and pyridine (1.0 equiv.) in DCM (concentration, 0.4 M) was cooled in an ice bath. Thesolution of 2-chloroacetyl chloride or 2-bromoacetyl bromide (1.1 equiv.) in DCM (concentration, 0.5 M) was added dropwise to theabove solution according to the references [1-3]. The resulting reaction mixture was warmed to room temperature and stirred for 12 h.The reaction mixture was diluted with DCM and then washed with 1M HCl and brine. The organic layer was dried over anhydrousMgSO4, filtered and concentrated in vacuo. The crude product was purified by crystallization from a mixture of solvent DCM andpetroleum ether.
61% Stage #1: 4-trifluoromethylphenylamine With potassium carbonate In dichloromethane at 0℃; for 0.25h; Inert atmosphere; Stage #2: chloroacetyl chloride In dichloromethane at 0 - 20℃; for 2h; Inert atmosphere; 4.1.1 General procedure for synthesis of 2-chloro-N-phenyl substituted acetamides (2a-2t and 5a-5b) General procedure: To a solution of substituted aniline (compounds 1a-1t) or 5-aminoindole and 6-aminoquinoline (1.0 equiv.) in dichloromethane (CH2Cl2) (15mL) at 0°C, potassium carbonate (K2CO3) (2.0 equiv.) was added. The reaction was stirred at 0°C for 15min. Into this stirring solution, chloroacetyl chloride (1.0 equiv.) was added dropwise at 0°C. The mixture was stirred for 2hat room temperature. After completion of the reaction, water (20mL) was added, and the mixture was extracted with dichloromethane. The organic solvent phase was concentrated under vacuum to afford the desired compounds 2a-2t, 5a and 5b.
42% Stage #1: 4-trifluoromethylphenylamine With triethylamine In dichloromethane at 20℃; for 0.166667h; Stage #2: chloroacetyl chloride In dichloromethane at 20℃; 4.5.15. 2-Chloro-N-(4-trifluoromethyl-phenyl)-acetamide (20) Procedure as for 14 except using 4-trifluoromethylaniline(1.9 mL, 15 mmol). Pure 20 was obtained as a yellow powder (1.5 g, 42%). m/z (ES), found 235.6225 (C9H6ClF3NO [MH])requires 236.0168; δH/ppm (400 MHz, d6-DMSO): 10.64 (1H, s,NH), 7.80 (2H, d, J = 8.5, Ar-H), 7.70 (2H, d, J = 8.6, Ar-H), 4.30(2H, s, CH2).
31% With sodium hydroxide In water monomer
With triethylamine In dichloromethane at 5℃; for 0.5h;
With anhydrous sodium carbonate In toluene at 20℃; for 1.5h;
With triethylamine In dichloromethane at -5 - 20℃;
In dichloromethane at 0 - 23℃;
Stage #1: 4-trifluoromethylphenylamine With potassium carbonate In dichloromethane at 20℃; for 0.5h; Stage #2: chloroacetyl chloride In dichloromethane at 20℃; Reflux; 2.2.1. Step 1: synthesis of 2-chloro-N-(4-nitrophenyl)acetamide General procedure: A suspension of 4-nitroaniline (7 g, 0.051 mol) and anhydrouspotassium carbonate (7 g, 0.051 mol) in dichloromethane (30 mL)was stirred for 30 min at room temperature. The reaction mixturewas cooled on an ice bath. To this was added an ice-cooled solutionof chloroacetylchloride (5.7 g, 0.051 mol) in dichloromethane(20 mL) drop wise over a period of 30 min. The reaction mixturewas stirred overnight at room temperature followed by reflux foradditional 30 min. Excess solvent was removed and the residuewas neutralized with aqueous sodium bicarbonate solution (5%w/v). The product obtained was filtered off and washed thoroughlywith cold water. The crude product obtained was dried under vacuum(10 g, yield: 92%). TLC (chloroform, Rf = 0.5). The product wassufficiently pure and used in the next step directly.
With potassium carbonate In dichloromethane
With potassium carbonate In acetone at 0 - 20℃; for 0.5h;
With triethylamine In 1,4-dioxane at 0 - 5℃;
With triethylamine In dichloromethane at 0℃;
With sodium hydroxide at 20℃;
In glacial acetic acid at 0 - 20℃; 4.2. General procedure for synthesis of benzaldehydes required forthe preparation of compounds 35-72 General procedure: Various substituted anilines were dissolved in glacial acetic acidat 0 °C, to this was added over 30 min choloroacetylchloride (2equivalents). The reaction mixture was brought to room temperatureand stirred overnight. Saturated sodium bicarbonate solutionwas added till complete neutralization. The resulting precipitatewas filtered off and washed with n-hexane and dried. The resultantproduct was used further without any purification. Either of 3-hydroxy benzaldehyde, 4-hydroxy benzaldehyde, vanillin or isovanillin(1 equivalent) was dissolved in acetone and potassiumcarbonate (2 equivalents) was added. Then correspondingsubstituted acetamide was mixed to the stirring solution. Finally,potassium iodide (1.5 equivalent) was added. The reaction mixturewas refluxed for 8-10 h. After completion of reaction, the resultantmixture was concentrated and treated with water and extractedwith ethyl acetate (3 x 20 mL). The organic layers were combinedand treated with brine and dried over sodium sulfate andconcentrated. The crude mixture was purified over silica gel(60-120) using petroleum ether: ethyl acetate (9:1).
With triethylamine In dichloromethane at 20℃; for 1h; General synthetic procedure of intermediate 5 General procedure: A substituted aniline (5.0 mmol) and triethylamine (1.87 g,18.5 mmol) were dissolved by dichloromethane (10 mL),and stirred under an ice-water bath, to which chloroacetylchloride (1.29 g, 11.5 mmol) was added dropwise. Afteraddition, the reaction mixture was stirred for one more hourat room temperature, then EA (30 mL) and H2O (30 mL)were added for an extraction. The organic contract waswashed with water (15 mL × 3) and saturated brine (15 mL),dried over Na2SO4 and evaporated under reduced pressureto afford intermediate 5.
With triethylamine In tetrahydrofuran at 0 - 20℃; for 2h; 4.1.4. General procedure for the synthesis of azide substituents(N23-N27 and N34-N36) General procedure: B23-B27 or B34-B361.0 mmol, 1.0 equiv) and Et3N (1.2 mmol,1.2 equiv) were dissolved in anhydrous tetrahydrofuran (THF), thena solution of chloroacetyl chloride (1.1 mmol, 1.1 equiv) in anhydrousTHF was added dropwise at 0 C. The reaction mixture wasthen stirred at room temperature for additional 2 h. Then water(30 mL) was added, extracted with ethyl acetate (3 10 mL). Theorganic phase was combined, dried over anhydrous Na2SO4,filtered, and concentrated to yield the crude azide substituents,which was purified by flash column chromatography to afford intermediatesC23eC27 and C34eC36. To a solution of the intermediatesin DMF were added sodium azide (1.2 mmol,1.2 equiv),and the mixture was stirred for 24 h at room temperature. Thenwater (30 mL) was added, extracted with ethyl acetate (3 10 mL).The organic phase was combined, dried over anhydrous Na2SO4,filtered, and concentrated to yield the target azide substituentsN23eN27 and N34eN36, which were used for the next stepwithout further purification.
With triethylamine In dichloromethane Cooling with ice; 12.3 third step:P-trifluoromethylaniline as raw material,Dichloromethane as a solvent,Add triethylamine (1 mmol),Under ice conditions,Chloroacetyl chloride (1 mmol) diluted slowly with dichloromethane using a constant pressure dropping funnel,After completing the reaction, pour the system into water, adjust the pH to weakly basic with Na2CO3, extract with dichloromethane, and concentrate the organic phase under reduced pressure.2-chloro-N- (4- (trifluoromethyl) phenyl) acetamide.
With triethylamine In dichloromethane at 20℃; for 5h; General procedure for the synthesis of compounds 6a-6k. General procedure: 2-Chloroacetamide (6a) was purchased from Sigma Aldrich; the synthesis of the titled compounds was achieved by following the reported methods,1-5 with an overall yield of 80%, and confirmed by 1H NMR. Briefly,chloroacetylchloride (5) (1.4 equiv.) was added dropwise to a solution of Et3N (2 equiv.) and the corresponding aniline (4b-4k) (1 equiv.) in dry dichloromethane (20 mL). The reaction mixturewas stirred for 5h at RT and monitored by TLC. Once completed (as judged by TLC), ethyl acetate(20 mL) were added to the reaction mixture, which yielded a precipitated in the form of whitecrystals, which were removed by filtration; the filtered solution was washed with water (3x, 20mL) and dried with MgSO4. Ethyl acetate was removed under reduced pressure, to yield a powderthat was recrystallized from a mixture of hexane and ethyl acetate (90:10).
Stage #1: 4-trifluoromethylphenylamine With triethylamine In dichloromethane at 20℃; for 0.5h; Stage #2: chloroacetyl chloride In dichloromethane Cooling with ice; Synthesis of compound 2 General procedure: Appropriate amine (10.0 mmol), triethylamine (12.0 mmol), and 30 ml CH2Cl2 were placed in a 100 ml round-bottomed flask, and the resulting mixture was stirred for 0.5 h at room tempera- ture. A solution of ClCH2COCl (12.0 mmol) in 5 ml of CH2Cl2 was added drop wise to the mixture in an ice-bath. After the reaction was completed, the solvent was removing under reduced pressure to obtain a white solid.
In dichloromethane at 0 - 20℃;
With triethylamine In dichloromethane Cooling with ice;
Stage #1: 4-trifluoromethylphenylamine; chloroacetyl chloride In glacial acetic acid at 10 - 15℃; for 0.5h; Stage #2: With anhydrous Sodium acetate In water monomer; glacial acetic acid at 20℃; for 1.5h;
With triethylamine In acetone at 20℃; for 1.5h;
With triethylamine In dichloromethane
320 mg With triethylamine In dichloromethane at 0℃; for 1h; General procedure A: General procedure: To a stirred solution of substituted amine (0.90 mmoL) in CH2Cl2 (2.0mL) was added triethylamine (1.35 mmoL) and chloroacetyl chloride (1.08 mmoL) at 0 oC. Afterstirring the reaction mixture for 1h, the reaction mixture is diluted with CH2Cl2 (10 mL), washedwith NaHCO3, the organic layer was dried over Na2SO4, and then concentrated under high vacuumto give crude chloroacetyl derivative. To a crude chloroacetyl derivative in THF (2 mL) was addedsodium 1H-1,2,3-triazole-5-thiolate (0.054 mmoL), the mixture was heated at 70 oC for 1h. Thesolids were filtered off and the filtrate was evaporated under high vacuum to give crude product.The crude product was purified over silica-gel column chromatography (Eluents: 20 - 50% EtOAcin hexane) to produce pure compound.

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  • 2
  • [ 2707-23-5 ]
  • [ 90774-69-9 ]
YieldReaction ConditionsOperation in experiment
91.4% With thionyl chloride In methanol for 1h; Reflux;
  • 3
  • [ 2707-23-5 ]
  • [ 578-95-0 ]
  • [ 389577-18-8 ]
YieldReaction ConditionsOperation in experiment
62% Stage #1: 10H-acridin-9-one With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0℃; for 2h; Stage #2: 2-chloro-N-(4-trifluomethylphenyl)acetamide With potassium iodide In N,N-dimethyl-formamide; mineral oil at 0℃; Reflux; 4.1. General synthetic procedure for 2-(9-oxoacridin-10(9H)-yl)-N-(substituted) phenyl acetamide (13a-o) General procedure: Acridone (10) (195mg, 1mmol) was added portion wise to a stirred suspension of NaH (56mg, 1.2mmol, 50% of mineral oil) in dry DMF (10ml) at 0°C. The reaction mixture was stirred for 2h. Afterward, 2-chloro-N-(substituted)phenyl acetamides 12a-o (2mmol) and KI (33.2mg, 0.2mmol) were added to the reaction mixture with stirring for different time intervals. After completion of the reaction (TLC), the reaction mixture was poured into crushed ice (50g) with constant stirring. The precipitated solid was collected and then extracted with chloroform. The combined organic extracts were washed with brine and water and finally dried with anhydrous sodium sulfate. Pure compounds were isolated after column chromatography and recrystallized from suitable solvent.
  • 4
  • [ 2707-23-5 ]
  • [ 162148-48-3 ]
  • 1,7-bis(tert-butoxycarboxymethyl)-4,10-[4-(trifluoromethyl)phenyl]acetamide}-1,4,7,10-tetraazacyclododecane [ No CAS ]
  • 5
  • [ 2707-23-5 ]
  • [ 31130-17-3 ]
  • C12H10F3N3O2S [ No CAS ]
YieldReaction ConditionsOperation in experiment
With potassium carbonate In acetone
Same Skeleton Products
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