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Structure of 83345-11-3

Chemical Structure| 83345-11-3

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Product Details of [ 83345-11-3 ]

CAS No. :83345-11-3
Formula : C10H13NO2
M.W : 179.22
SMILES Code : CC(NC1=CC=C(CCO)C=C1)=O
MDL No. :MFCD01536093
Boiling Point : No data available
InChI Key :VYEJXTZQKRHBHH-UHFFFAOYSA-N
Pubchem ID :3295905

Safety of [ 83345-11-3 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H332-H335
Precautionary Statements:P261-P280-P305+P351+P338

Application In Synthesis of [ 83345-11-3 ]

* 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 [ 83345-11-3 ]

[ 83345-11-3 ] Synthesis Path-Downstream   1~21

  • 1
  • [ 83345-11-3 ]
  • acetic acid-[4-(2-hydroxy-ethyl)-2-nitro-anilide] [ No CAS ]
  • 2
  • [ 108-24-7 ]
  • [ 104-10-9 ]
  • [ 83345-11-3 ]
YieldReaction ConditionsOperation in experiment
39.2% With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20℃; for 4.0h; . To a stirred solution of 2-(4- aminophenyl)ethan-l-ol (500 mg, 3.64 mmol) and DIPEA (942.1 mg, 7.29 mmol) in DCM (10 mL) was added Ac20 (372.1 mg, 3.64 mmol) dropwise at room temperature. The resulting mixture was stirred for 4 h at room temperature, then was concentrated and the residue was purified on silica gel column with EA/PE (1/1) to afford N-[4-(2- hydroxyethyl)phenyl] acetamide (256 mg, 39.2%) as an off-white solid. ES-MS (m/z): [M+l]+ = 180.
  • 3
  • [ 83345-11-3 ]
  • [ 166272-81-7 ]
  • 3-[2-(4-acetylamino-phenyl)-ethoxy]-4-chloro-benzoic acid methyl ester [ No CAS ]
  • 4
  • [ 83345-11-3 ]
  • [ 214822-96-5 ]
  • 3-[2-(4-acetylamino-phenyl)-ethoxy]-4-fluoro-benzoic acid methyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
(c) 4'-(2-Hydroxyethyl)acetanilide A solution of the product from step (b) (55.3 g) in methanol (250 ml) and 1N aqu. NaOH (500 ml) was stirred at room temperature for 1 hour. The methanol was evaporated in vacuo and the remaining aqueous solution adjusted to pH 4 (2N aqu. HCl), saturated with NaCl, and extracted with ethyl acetate (*3). The combined extracts were washed with water and brine, dried over MgSO4 and evaporated in vacuo to give a brown oil which was flash chromatographed through a silica column using ethyl acetate and then crystallized from ethyl acetate to give the desired product (51.7 g).
  • 6
  • [ 83345-11-3 ]
  • [ 1085309-04-1 ]
  • 7
  • [ 1108732-85-9 ]
  • [ 83345-11-3 ]
  • [ 1108732-86-0 ]
  • 8
  • [ 83345-11-3 ]
  • [ 123-62-6 ]
  • [ 1108732-92-8 ]
  • 9
  • [ 83345-11-3 ]
  • [ 98-59-9 ]
  • [ 1108732-89-3 ]
  • 10
  • [ 83345-11-3 ]
  • [ 1956-06-5 ]
  • [ 100-02-7 ]
  • [ 1108732-92-8 ]
  • 11
  • [ 75178-16-4 ]
  • [ 83345-11-3 ]
  • 12
  • [ 83345-11-3 ]
  • [ 155164-63-9 ]
  • [ 75178-16-4 ]
YieldReaction ConditionsOperation in experiment
93% In neat (no solvent); at 100℃; for 0.166667h;Sealed tube; Green chemistry; General procedure: Alcohol(1, 5.31 mmol, 1 equiv.) and 2-acylpyridazin-3(2H)-ones (2,6.37 mmol, 1.2 equiv.) were placed in a culture tube (Pyrexbrand 9825 culture tube with screw cap), sealed, and heatedto 100 C. The resulting mixture was kept at this temperatureuntil 1 disappeared (as determined by TLC analysis). Aftercooling of the tube, dichloromethane (5-6 mL) was added tothe mixture with stirring until the reaction mixture wasdissolved. After removing 4,5-dichloropyridazin-3(2H)-oneby filtration, the resulting filtrate was evaporated underreduced pressure. The resulting residue was further purifiedby silica gel column chromatography to give the correspondingesters 3.
86% In tetrahydrofuran; at 150℃; under 10336.0 Torr; for 0.08333330000000001h;Microwave irradiation; General procedure: Alcohol (2 or 5, 5.31 mmol, 1 equiv) and 2-acylpyridazin-3(2H)-ones (1k or 4, 6.37 mmol, 1.2 equiv) were placed in a capped vial without solvent or in the presence of tetrahydrofuran (5 mL, 6f and 6g) at room temperature. The resulting mixture was irradiated in aMWoven (300Woutput,1378 kPa) at 150 C for 5 min, until 1k or 4 was consumed. The reaction was monitored by TLC. After cooling Phenyl acetate (3) of the reaction vial, the product was extracted with dichloromethane (6 mL). The reaction mixture was filtered, and the resultant filtrate was evaporated under reduced pressure. The resulting residue was purified further by silica gel column chromatography to give the corresponding esters 3 and 6 4-Acetamidophenethyl acetate (6a) Yield: 276 mg, 86%. White solid. Mp 96-98 C (lit. 13 mp 95 C). IR (KBr, CH2Cl2) 3293, 3186, 3119, 3061, 2952, 2928, 2885, 1732, 1663, 1603, 1534, 1408, 1368, 1315, 1262, 1034, 835, 753 cm-1. 1H NMR (300 MHz, CDCl3) δ 2.03 (s, 3H), 2.15 (s, 3H), 2.89 (t, 2H, J1 and J2=7.0 Hz), 4.24 (t, 2H, J1 and J2=7.0 Hz), 7.15 (d, 2H, J=8.37 Hz), 7.43 (d, 2H, J=8.41 Hz), 7.55 (br s, 1H, D2O exchangeable). 13C NMR (75 MHz, CDCl3) δ 20.97, 24.50, 34.48, 54.91, 120.12, 129.38, 133.75, 136.50, 168.46, 171.11. HRMS (m/z): [M]+ calcd for C12H15NO3 221.1052. Found: 221.1056.
  • 13
  • [ 83345-11-3 ]
  • [ 100-52-7 ]
  • N-(2-benzoyl-4-(2-hydroxyethyl)phenyl)acetamide [ No CAS ]
  • 14
  • [ 83345-11-3 ]
  • [ 104-87-0 ]
  • N-(4-(2-((4-methylbenzyl)oxy)ethyl)phenyl)acetamide [ No CAS ]
  • 15
  • [ 102494-22-4 ]
  • [ 83345-11-3 ]
  • 16
  • [ 83345-11-3 ]
  • C10H10FNO4S [ No CAS ]
  • 18
  • [ 83345-11-3 ]
  • [ 6325-43-5 ]
  • [ 99701-07-2 ]
  • 19
  • [ 83345-11-3 ]
  • [ 39232-06-9 ]
  • 20
  • [ 83345-11-3 ]
  • 4-chloro-5-(2-methyl-6-(trifluoromethyl)pyridin-4-yl)-6-phenylpyrimidin-2-amine [ No CAS ]
  • N-(4-(2-((2-amino-5-(2-methyl-6-(trifluoromethyl)pyridin-4-yl)-6-phenylpyrimidin-4-yl)oxy)ethyl)phenyl)acetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
21.2% With caesium carbonate; In N,N-dimethyl-formamide; at 80℃; for 16.0h;Inert atmosphere; To a mixture of N-[4-(2- hydroxyethyl)phenyl] acetamide (35.0 mg, 0.20 mmol) and 4-chloro-5-[2-methyl-6- (trifluoromethyl)pyridin-4-yl]-6-phenylpyrimidin-2-amine(7l.2 mg, 0.20 mmol) in DMF (2 mL) was added Cs2C03 (127.3 mg, 0.39 mmol) at room temperature under nitrogen atmosphere. The resulting mixture was stirred for 16 h at 80 C. After cooling to room temperature, the mixture was filtered and the solid cake was washed with DMF (2 x 0.5 mL). The combined filtrate was purified by Prep-HPLC to obtain N-(4-(2-((2-amino-5-(2-methyl-6-(trifluoromethyl)pyridin-4- yl)-6-phenylpyrimidin-4-yl)oxy)ethyl)phenyl)acetamide (21 mg, 21.2%) as a white solid. ES- MS (m/z) [M+l]+= 508.2.
  • 21
  • [ 100-27-6 ]
  • [ 83345-11-3 ]
 

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