Home Cart 0 Sign in  
X

[ CAS No. 13334-49-1 ] {[proInfo.proName]}

,{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]}
3d Animation Molecule Structure of 13334-49-1
Chemical Structure| 13334-49-1
Chemical Structure| 13334-49-1
Structure of 13334-49-1 * Storage: {[proInfo.prStorage]}
Cart0 Add to My Favorites Add to My Favorites Bulk Inquiry Inquiry Add To Cart

Quality Control of [ 13334-49-1 ]

Related Doc. of [ 13334-49-1 ]

Alternatived Products of [ 13334-49-1 ]

Product Details of [ 13334-49-1 ]

CAS No. :13334-49-1 MDL No. :MFCD00014355
Formula : C10H12O3 Boiling Point : -
Linear Structure Formula :- InChI Key :XRTZHWXWLUGOAT-UHFFFAOYSA-N
M.W : 180.20 Pubchem ID :83354
Synonyms :

Safety of [ 13334-49-1 ]

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

Application In Synthesis of [ 13334-49-1 ]

* 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 [ 13334-49-1 ]

[ 13334-49-1 ] Synthesis Path-Downstream   1~36

  • 1
  • [ 13334-49-1 ]
  • [ 34135-75-6 ]
YieldReaction ConditionsOperation in experiment
With lithium aluminium tetrahydride; diethyl ether
  • 2
  • [ 35471-28-4 ]
  • [ 105-36-2 ]
  • [ 13334-49-1 ]
YieldReaction ConditionsOperation in experiment
With ethanol anschliessend Erwaermen mit wss. NaOH;
  • 3
  • furan-2,3,5(4H)-trione pyridine (1:1) [ No CAS ]
  • [ 79-11-8 ]
  • [ 105-67-9 ]
  • [ 13334-49-1 ]
  • 4
  • [ 79-11-8 ]
  • [ 105-67-9 ]
  • [ 13334-49-1 ]
YieldReaction ConditionsOperation in experiment
With sodium hydroxide
With sodium hydroxide
With sodium hydroxide Heating;
With potassium carbonate In acetone for 8h; Reflux;
With sodium hydroxide In water General procedure for the synthesis of aryloxy acetic/propionicacids (2a-q and 3a-q) General procedure: Equimolar quantities of 2-chloro acetic acid/3-chloro propionicacid (0.05 mol) and appropriate phenol (1a-q) (0.05 mol) were taken in a conical flask, to which aqueous solution of NaOH(0.12 mol in 25 mL water) was slowly added with constant stirring.The solution was stirred for 2 h until the solution turned clear,brown or yellow and then the reaction mixture was evaporatedin a evaporating dish until the solid sodium salt was precipitated. The salt was isolated, dried, dissolved in water and acidified byadding con. HCl. The precipitated aryloxy acetic/propionic acidwas filtered and recrystallized from water or ethanol

  • 5
  • [ 123-75-1 ]
  • [ 13334-49-1 ]
  • 2-(2,4-Dimethyl-phenoxy)-1-pyrrolidin-1-yl-ethanone [ No CAS ]
YieldReaction ConditionsOperation in experiment
63% With dicyclohexyl-carbodiimide In diethyl ether for 14h; Ambient temperature;
  • 6
  • [ 110-91-8 ]
  • [ 13334-49-1 ]
  • 2-(2,4-Dimethyl-phenoxy)-1-morpholin-4-yl-ethanone [ No CAS ]
YieldReaction ConditionsOperation in experiment
80% With dicyclohexyl-carbodiimide In ethyl acetate for 14h; Ambient temperature;
  • 7
  • [ 110-85-0 ]
  • [ 13334-49-1 ]
  • 2-(2,4-Dimethyl-phenoxy)-1-{4-[2-(2,4-dimethyl-phenoxy)-acetyl]-piperazin-1-yl}-ethanone [ No CAS ]
YieldReaction ConditionsOperation in experiment
77% With dicyclohexyl-carbodiimide In chloroform for 14h; Ambient temperature;
  • 8
  • [ 13334-49-1 ]
  • [ 4413-43-8 ]
  • 3-(4-Chloro-phenoxymethyl)-6-(2,4-dimethyl-phenoxymethyl)-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
61% With trichlorophosphate for 5h; Heating;
  • 9
  • [ 64-17-5 ]
  • [ 13334-49-1 ]
  • [ 176450-08-1 ]
YieldReaction ConditionsOperation in experiment
With sulfuric acid
  • 10
  • [ 302-17-0 ]
  • [ 13334-49-1 ]
  • {5-[1-(5-carboxymethoxy-2,4-dimethyl-phenyl)-2,2,2-trichloro-ethyl]-2,4-dimethyl-phenoxy}-acetic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
With sulfuric acid
YieldReaction ConditionsOperation in experiment
neben 2,4-Xylenol-methylether: 2,4-Xylenol, Betain, CaO, 155grad-190grad;
2,4-Dimethyl-phenol, wss. NaOH, Chloressigsaeure, 100grad, 2 Std.;
  • 12
  • [ 13334-49-1 ]
  • [ 72293-69-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: conc. sulphuric acid 2: hydrazine hydrate
  • 13
  • [ 13334-49-1 ]
  • [ 2731-16-0 ]
  • N-deacetyl-N-(2,4-dimethylphenoxyacetyl)thiocolchicine [ No CAS ]
YieldReaction ConditionsOperation in experiment
With dmap In dichloromethane at 20℃; for 10h; 2.A The reaction mixture of N-deacetylthiocolchicine (22 mg, 0.06 mmol), 2,4-dimethlphenoxyacetic acid (25 mg, 0.13 mmol), DMAP (2 mg, 0.2 mmol) DMAP (2 mg, 0.2 mmol) and dichloromethane (3 ml) was stirred at room temperature for 10 h. Then dichloromethane (20 ml) was added. Organic layer was washed with H2O, 5% Na2CO3 and brine, and then dried over MgSO4. After the solvent was removed under vacuum, the residue was separated by column chromatography (eluent: ethyl acetate and petroleum ether) to afford 26.3 mg N-Deacetyl-N-(2,4-dimethylphenoxyacetyl)thiocolchicine, mp 85-87°(dec.). [0237] The chemical structure analysis was performed by 1HNMR (CDCl3, 600 MHz); δ 7.28 (d, 1H, H8), 7.18 (s, 1H, H12), 7.05-6.96 (m, 4H, NH, Ar-h and H11), 6.67 (d, 1H, Ar-H), 6.54 (s, 1H, H4), 4.70 (m, 1H, H7), 4.47, 4.38 (dd, 2H, COCH2O), 3.95 (s, 3H, OCH3), 3.91 (s, 3H, OCH3), 3.68 (s, 3H, OCH3), 2.44 (s, 3H, SCH3), 2.30 (s, 3H, Ar-CHs), 2.28 (s, 3H, Ar-CH3), 2.60-1.09 (m, 4H, H5, 6).
  • 14
  • [ 13334-49-1 ]
  • [ 141-43-5 ]
  • [ 1063737-99-4 ]
YieldReaction ConditionsOperation in experiment
Microwave irradiation;
  • 15
  • [ 13334-49-1 ]
  • 2-(2,5-dimethyl-1H-pyrrol-1-yl)-5-((2,4-dimethylphenoxy)methyl)-1,3,4-thiadiazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: trichlorophosphate / 0.5 h / 75 °C 1.2: 4 h / Reflux 2.1: acetic acid / 1 h / Reflux
  • 16
  • [ 13334-49-1 ]
  • 2-((2,4-dimethylphenoxy)methyl)-5-(1H-pyrrol-1-yl)-1,3,4-thiadiazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: trichlorophosphate / 0.5 h / 75 °C 1.2: 4 h / Reflux 2.1: acetic acid / 1 h / Reflux
  • 17
  • [ 13334-49-1 ]
  • [ 79-19-6 ]
  • [ 119869-04-4 ]
YieldReaction ConditionsOperation in experiment
Stage #1: 2-(2,4-dimethylphenoxy)acetic acid; thiosemicarbazide With trichlorophosphate at 75℃; for 0.5h; Stage #2: In water for 4h; Reflux; General procedure for the preparation of 2-((phenoxy orsubstituted phenoxy)methyl/ethyl)-1,3,4-thiadiazol-5-amines (4a-qand 5a-q) General procedure: A mixture of benzoic acid (50 mmol), N-aminothiourea(50 mmol) and POCl3 (13 mL) was heated at 75 C for 0.5 h. Themixture was cooled to which water (10 mL) was added and thereaction mixture was refluxed for 4 h. The mixture was cooled and pH was adjusted to 8.0 by adding 50% sodium hydroxide solution.The separated solid was filtered and recrystallized from ethanolto give desired compounds.
  • 18
  • [ 13334-49-1 ]
  • tert-butyl 3-(4-[hydrazinyl(thioxo)acetyl]amino}phenyl)propanoate [ No CAS ]
  • 3-{4-[({5-[(2,4-dimethylphenoxy)methyl]-1,3,4-thiadiazol-2-yl}carbonyl)amino]phenyl}propanoic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
39% Stage #1: 2-(2,4-dimethylphenoxy)acetic acid With 1,1'-carbonyldiimidazole In dichloromethane at 20℃; for 0.5h; Inert atmosphere; Stage #2: tert-butyl 3-(4-[hydrazinyl(thioxo)acetyl]amino}phenyl)propanoate In dichloromethane at 20℃; for 16h; Inert atmosphere; Further stages; General procedure for the preparation of compounds 4a-uand 5a-q General procedure: To a solution of the respective carboxylic acid (8a-u or 9,0.5 mmol) in DCM (4 mL) carbonyl-1,10-diimidazole (0.55 mmol,90 mg) was added and the mixture was stirred at r. t. for 30 min. Tothe resulting solution of the carboxylic acid imidazolide, respectivethiohydrazide (7 or 10a-q) was added and the reaction mixturewasstirred at r. t. for 16 h. The solvent was removed in vacuo, the residuewasdissolved in glacial acetic acid (3 mL) and the solutionwasheated at reflux for 30 min. It was then cooled down to r. t., pouredinto water (50 mL), the resulting precipitate was collected byfiltration and dried in vacuo. It was then combined with 4 M solutionof HCl in 1,4-dioxane (5 mL); the mixture was stirred at r. t.for 16 h and poured into water (50 mL). The precipitate wascollected by filtration, washed with water and air-dried to providethe title compounds in yields indicated.
  • 19
  • [ 13334-49-1 ]
  • C19H32N2O3 [ No CAS ]
  • C29H42N2O5 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; triethylamine In N,N-dimethyl-formamide at 20℃; for 10h; General procedure: To the mixture of compound 16 and the phenol relatedacetic acid derivative in DMF was added TBTU and Et3N,and stirred at room temperature for 10 hours. After evaporationof the solvent, the residue was purified on silica gel columnto afford 18, or 19, or 20 in 50-70% yield. By usingsimilar procedure, compounds 15 and 17 were converted into the amides 21 and 22. Products 18, 19, 20, 21 and 22 wereconfirmed by LCMS. Then compounds 21 or 22 were treatedby TFA/CH2Cl2 (9:1) for 30 min. After removal of the solventby co-evaporation with toluene, the residue was treatedwith N-phenylsulfonyl-valine in dry DMF in the presence ofTBTU and Et3N for 10 hours at room temperature under nitrogen.The volatiles of the reaction mixture were evaporatedand the residue was diluted with aqueous NaHCO3 and extractedwith CH2Cl2. Then the combined extracts wereevaporated and the residue was dissolved into ether and precipitatedwith hexane and filtered. The precipitated solidswere then dissolved into a mixture of CH2Cl2/MeOH, andmixed with a minimum amount of silica gel. After evaporatingthe volatiles, the silica gel adsorbed with the compoundswas loaded onto a silica gel column, and was washed withdichloromethane/ethyl acetate (3:1), then using methanol towash the column. The methanol fraction was concentrated,and the residue was suspended in hexane/ethyl acetate (1:1)and the solid product was filtered and washed with the samemixture to obtain the desired products 3, 4, 5, 23a, 23b and23c in more than 90% purities based on LCMS analysis.
  • 20
  • [ 1108137-69-4 ]
  • [ 13334-49-1 ]
  • 1-(2,4-dimethyl-phenoxyacetyl)-lycorine [ No CAS ]
YieldReaction ConditionsOperation in experiment
57.2% Stage #1: (1S,2S,3a1S,12bS)-2-((tert-butyldimethylsilyl)oxy)-2,3a1,4,5,7,12b-hexahydro-1H-[1,3]dioxolo[4,5-j]pyrrolo[3,2,1-de]phenanthridin-1-ol; 2-(2,4-dimethylphenoxy)acetic acid With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; Stage #2: With tetrabutyl ammonium fluoride In tetrahydrofuran at 20℃; 13 Example 13: 1- (2,4-dimethyl-phenoxyacetyl) -lycoline (13) 13-a: 2-TBS-lycoline (1.0 mmol), 2,4-dimethyl-phenoxyacetic acid (1.2 mmol), EDCI (1.2 mmol), DMAP (0.12 mmol), 15 ml of dichloromethane, Place in a 50ml reaction flask and stir at room temperature until no raw materials remain. Transfer to a separatory funnel, add 50 ml of dichloromethane, wash the organic phase with saturated sodium bicarbonate solution, water, and saturated sodium chloride solution, dry over anhydrous sodium sulfate, and concentrate for later use.13-b: Put the above product, TBAF (2.0 mmol), 15 ml of THF, into a 50 ml reaction bottle, and stir at room temperature until no raw materials remain. Transfer to a separatory funnel, add 50 ml of dichloromethane, wash the organic phase with saturated sodium bicarbonate solution, water, saturated sodium chloride solution, dry over anhydrous sodium sulfate, concentrate, and separate by column chromatography to obtain a yellow solid (57.2% ).
  • 21
  • [ 13334-49-1 ]
  • 2-(2-(2,4-dimethylphenoxy)acetyl)-3-hydroxycyclohex-2-en-1-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; dmap / dichloromethane / 20 °C / Inert atmosphere 2: triethylamine; 2-hydroxy-2-methylpropanenitrile / dichloromethane / 24 h / 20 °C / Inert atmosphere
  • 22
  • [ 13334-49-1 ]
  • 2-(2-(2,4-dimethylphenoxy)acetyl)-3-hydroxy-5,5-dimethylcyclohex-2-en-1-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; dmap / dichloromethane / 20 °C / Inert atmosphere 2: triethylamine; 2-hydroxy-2-methylpropanenitrile / dichloromethane / 24 h / 20 °C / Inert atmosphere
  • 23
  • [ 13334-49-1 ]
  • 2-(2,4-dimethylphenoxy)-1-(5-hydroxy-1,3-dimethyl-1H-pyrazol-4-yl)ethan-1-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; dmap / dichloromethane / 20 °C / Inert atmosphere 2: triethylamine; 2-hydroxy-2-methylpropanenitrile / dichloromethane / 24 h / 20 °C / Inert atmosphere
  • 24
  • [ 13334-49-1 ]
  • 1-(3-cyclopropyl-5-hydroxy-1-methyl-1H-pyrazol-4-yl)-2-(2,4-dimethylphenoxy)ethan-1-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; dmap / dichloromethane / 20 °C / Inert atmosphere 2: triethylamine; 2-hydroxy-2-methylpropanenitrile / dichloromethane / 24 h / 20 °C / Inert atmosphere
  • 25
  • [ 13334-49-1 ]
  • 2-(2,4-dimethylphenoxy)-1-(5-hydroxy-1-methyl-3-(trifluoromethyl)-1Hpyrazol-4-yl)ethan-1-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; dmap / dichloromethane / 20 °C / Inert atmosphere 2: triethylamine; 2-hydroxy-2-methylpropanenitrile / dichloromethane / 24 h / 20 °C / Inert atmosphere
  • 26
  • [ 199125-21-8 ]
  • [ 13334-49-1 ]
  • 3-cyclopropyl-1-methyl-1H-pyrazol-5-yl 2-(2,4-dimethylphenoxy)acetate [ No CAS ]
YieldReaction ConditionsOperation in experiment
54% With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; Inert atmosphere; General procedure for intermediate E1 - E40 General procedure: In the presence of DMAP as the catalyst to speed up the reaction, substituted 1,3-cyclohexanediones or substituted 1,3-dimethyl-1H-pyrazol-5-ol (0.1 mol), EDCI (0.1mol), anhydrous dichloromethane (DCM) (30 mL) and compound D (0.1 mol) wereadded to a 50 mL eggplant-shaped. The solution was stirred for 5-8 h. The progress ofthe reaction was monitored by TLC. After completion of the reaction, DCM was removed from the system under reduced pressure. Residues were purified via flashchromatography (Vethylacetate: Vpetroleumether =1:3) to afford the enol ester.
  • 27
  • [ 13334-49-1 ]
  • [ 122431-37-2 ]
  • C15H15F3N2O3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; Inert atmosphere; General procedure for intermediate E1 - E40 General procedure: In the presence of DMAP as the catalyst to speed up the reaction, substituted 1,3-cyclohexanediones or substituted 1,3-dimethyl-1H-pyrazol-5-ol (0.1 mol), EDCI (0.1mol), anhydrous dichloromethane (DCM) (30 mL) and compound D (0.1 mol) wereadded to a 50 mL eggplant-shaped. The solution was stirred for 5-8 h. The progress ofthe reaction was monitored by TLC. After completion of the reaction, DCM was removed from the system under reduced pressure. Residues were purified via flashchromatography (Vethylacetate: Vpetroleumether =1:3) to afford the enol ester.
  • 28
  • [ 13334-49-1 ]
  • [ 126-81-8 ]
  • C18H22O4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; Inert atmosphere; General procedure for intermediate E1 - E40 General procedure: In the presence of DMAP as the catalyst to speed up the reaction, substituted 1,3-cyclohexanediones or substituted 1,3-dimethyl-1H-pyrazol-5-ol (0.1 mol), EDCI (0.1mol), anhydrous dichloromethane (DCM) (30 mL) and compound D (0.1 mol) wereadded to a 50 mL eggplant-shaped. The solution was stirred for 5-8 h. The progress ofthe reaction was monitored by TLC. After completion of the reaction, DCM was removed from the system under reduced pressure. Residues were purified via flashchromatography (Vethylacetate: Vpetroleumether =1:3) to afford the enol ester.
  • 29
  • [ 13334-49-1 ]
  • [ 5203-77-0 ]
  • 1,3-dimethyl-1H-pyrazol-5-yl 2-(2,4-dimethylphenoxy)acetate [ No CAS ]
YieldReaction ConditionsOperation in experiment
64% With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; Inert atmosphere; General procedure for intermediate E1 - E40 General procedure: In the presence of DMAP as the catalyst to speed up the reaction, substituted 1,3-cyclohexanediones or substituted 1,3-dimethyl-1H-pyrazol-5-ol (0.1 mol), EDCI (0.1mol), anhydrous dichloromethane (DCM) (30 mL) and compound D (0.1 mol) wereadded to a 50 mL eggplant-shaped. The solution was stirred for 5-8 h. The progress ofthe reaction was monitored by TLC. After completion of the reaction, DCM was removed from the system under reduced pressure. Residues were purified via flashchromatography (Vethylacetate: Vpetroleumether =1:3) to afford the enol ester.
  • 30
  • [ 13334-49-1 ]
  • [ 504-02-9 ]
  • 3-oxocyclohex-1-en-1-yl 2-(2,4-dimethylphenoxy)acetate [ No CAS ]
YieldReaction ConditionsOperation in experiment
58% With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; Inert atmosphere; General procedure for intermediate E1 - E40 General procedure: In the presence of DMAP as the catalyst to speed up the reaction, substituted 1,3-cyclohexanediones or substituted 1,3-dimethyl-1H-pyrazol-5-ol (0.1 mol), EDCI (0.1mol), anhydrous dichloromethane (DCM) (30 mL) and compound D (0.1 mol) wereadded to a 50 mL eggplant-shaped. The solution was stirred for 5-8 h. The progress ofthe reaction was monitored by TLC. After completion of the reaction, DCM was removed from the system under reduced pressure. Residues were purified via flashchromatography (Vethylacetate: Vpetroleumether =1:3) to afford the enol ester.
  • 31
  • [ 95450-79-6 ]
  • [ 13334-49-1 ]
YieldReaction ConditionsOperation in experiment
86% Stage #1: (2,4-Dimethyl-phenoxy)-acetic acid methyl ester With potassium carbonate In water at 65℃; Inert atmosphere; Stage #2: With hydrogenchloride In water at 20℃; Inert atmosphere; General procedure for intermediate D1 - D40 General procedure: Compound C (0.1 mol), K2CO3 (0.15 mol) and water (50 mL) were added to a 100mL clean eggplant flask. After the reaction mixture was stirred for 5-10 h at 65 ,the reaction mixture was cooled to room temperature and was acidified with aqueous HCl solution (10%) to pH = 2-3. A white solid was afforded by filtration. After vacuum drying, product D was used in the next step. The analytical data corresponded to the literature [9-14].
  • 32
  • [ 105-67-9 ]
  • [ 13334-49-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: potassium carbonate / acetonitrile / 65 °C / Inert atmosphere 2.1: potassium carbonate / water / 65 °C / Inert atmosphere 2.2: 20 °C / pH 2 - 3 / Inert atmosphere
Multi-step reaction with 2 steps 1: potassium carbonate / N,N-dimethyl-formamide / 60 °C 2: lithium hydroxide / water; methanol; tetrahydrofuran / 20 °C
  • 33
  • [ 1108137-69-4 ]
  • [ 13334-49-1 ]
  • C32H41NO6Si [ No CAS ]
YieldReaction ConditionsOperation in experiment
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; 13.13-a 13-a: 2-TBS-lycorine (1.0 mmol), 2,4-dimethyl-phenoxyacetic acid (1.2 mmol), EDCI (1.2 mmol), DMAP (0.12 mmol), and dichloromethane (15 ml) were fed to a 50 ml reaction flask, and stirred at room temperature until no raw materials remained. The reaction solution was transferred to a separatory funnel, and dichloromethane (50 ml) was added. The organic phase was washed respectively with saturated sodium bicarbonate solution, water, and saturated sodium chloride solution, dried over anhydrous sodium sulfate, and concentrated for use.
  • 34
  • [ 176450-08-1 ]
  • [ 13334-49-1 ]
YieldReaction ConditionsOperation in experiment
With lithium hydroxide In tetrahydrofuran; methanol; water at 20℃;
  • 35
  • [ 27280-97-3 ]
  • [ 13334-49-1 ]
  • 2-(2,4-dimethylphenoxy)-N-(1-(1,1-dioxidotetrahydrothiophen-3-yl)-3-methyl-1H-pyrazol-5-yl)acetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
48% With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; triethylamine In dichloromethane; ethyl acetate at 20℃;
  • 36
  • [ 13334-49-1 ]
  • 2-(4-(1H-pyrrol-1-yl)phenoxy)acetohydrazide [ No CAS ]
  • 2-(4-(1H-pyrrol-1-yl)phenoxy)-N’-(2-(2,4-dimethylphenoxy)acetyl)acetohydrazide [ No CAS ]
YieldReaction ConditionsOperation in experiment
87% Stage #1: 2-(2,4-dimethylphenoxy)acetic acid; 2-(4-(1H-pyrrol-1-yl)phenoxy)acetohydrazide With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate In N,N-dimethyl-formamide for 0.25h; Stage #2: With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 25h; General procedure for the synthesis of 2-(4-(1H-pyrrol-1-yl)phenoxy)-N’-(2-phenoxyacetyl)acetohydrazides General procedure: 2-(4(1Hpyrrol-1-yl)phenoxy)acetohydrazide (4) (0.0019 mol) and different substituted phenoxy acids 5(a-k) (0.0018 mol) were dissolved in 30 mL of distilled dimethylformamide. HBTU (0.87 g, 0.0023 mol) was added and stirred for 15 min, then to the above mixture DIEA (0.93 mL, 0.0053 mol) was added and stirred for 25 h at room temperature. The reaction was quenched by adding 25% sodium chloride (30 mL) solution and mixture was extracted with ethyl acetate (3×50 mL). The collective ethyl acetate layer was washed with 1 N HCl (30 mL) and with saturated sodium bicarbonate (30 mL) solution, trailed by sodium chloride (30 mL). The organic layer was then dried over anhydrous sodium sulphate and was concentrated using a rotary flash evaporator. The formed precipitate was dried and purified by fractional column chromatography using ethyl acetate: petroleum ether (7:3) mixture as the eluent to get the pure titled compounds 6(a-k).
Same Skeleton Products
Historical Records

Related Functional Groups of
[ 13334-49-1 ]

Aryls

Chemical Structure| 1878-49-5

[ 1878-49-5 ]

2-(o-Tolyloxy)acetic acid

Similarity: 1.00

Chemical Structure| 13333-81-8

[ 13333-81-8 ]

2-(Mesityloxy)acetic acid

Similarity: 1.00

Chemical Structure| 13335-71-2

[ 13335-71-2 ]

2-(2,6-Dimethylphenoxy)acetic acid

Similarity: 1.00

Chemical Structure| 7356-41-4

[ 7356-41-4 ]

2-(2,5-Dimethylphenoxy)acetic acid

Similarity: 0.97

Chemical Structure| 2989-17-5

[ 2989-17-5 ]

Methyl 2-(o-tolyloxy)acetate

Similarity: 0.95

Ethers

Chemical Structure| 1878-49-5

[ 1878-49-5 ]

2-(o-Tolyloxy)acetic acid

Similarity: 1.00

Chemical Structure| 13333-81-8

[ 13333-81-8 ]

2-(Mesityloxy)acetic acid

Similarity: 1.00

Chemical Structure| 13335-71-2

[ 13335-71-2 ]

2-(2,6-Dimethylphenoxy)acetic acid

Similarity: 1.00

Chemical Structure| 7356-41-4

[ 7356-41-4 ]

2-(2,5-Dimethylphenoxy)acetic acid

Similarity: 0.97

Chemical Structure| 2989-17-5

[ 2989-17-5 ]

Methyl 2-(o-tolyloxy)acetate

Similarity: 0.95

Carboxylic Acids

Chemical Structure| 1878-49-5

[ 1878-49-5 ]

2-(o-Tolyloxy)acetic acid

Similarity: 1.00

Chemical Structure| 13333-81-8

[ 13333-81-8 ]

2-(Mesityloxy)acetic acid

Similarity: 1.00

Chemical Structure| 13335-71-2

[ 13335-71-2 ]

2-(2,6-Dimethylphenoxy)acetic acid

Similarity: 1.00

Chemical Structure| 7356-41-4

[ 7356-41-4 ]

2-(2,5-Dimethylphenoxy)acetic acid

Similarity: 0.97

Chemical Structure| 104295-97-8

[ 104295-97-8 ]

2-(2,3,6-Trimethylphenoxy)acetic acid

Similarity: 0.95