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N-(2-Chloroethyl)-N-ethylaniline
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[ CAS No. 92-49-9 ] {[proInfo.proName]}

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Chemical Structure| 92-49-9
Chemical Structure| 92-49-9
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Product Details of [ 92-49-9 ]

CAS No. :92-49-9 MDL No. :MFCD00000966
Formula : C10H14ClN Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W : 183.68 Pubchem ID :-
Synonyms :

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Application In Synthesis of [ 92-49-9 ]

* 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 [ 92-49-9 ]

[ 92-49-9 ] Synthesis Path-Downstream   1~3

  • 1
  • [ 92-50-2 ]
  • [ 92-49-9 ]
YieldReaction ConditionsOperation in experiment
60% With trichlorophosphate; In tetrahydrofuran; at 20℃; for 5h; The procedure described in Ref. [49] was used to prepare N-ethyl-N-(2-chloroethyl) aniline. A solution of POCl3 (3.30 g, 0.021 mol) in 10 mL of THF was added dropwise to a solution of N-ethyl-N-(2-hydroxyethyl)aniline(5.00 g, 0.03 mol) in THF under intensive stirring at room temperature for one hour. The reaction mixture was stirred for 4 h. The solvent was evaporated, the residue was diluted with an aqueous solution of NaHCO3, the product was extracted with CH2Cl2 (20 mL). The extract was dried over MgSO4, filtered, and the solvent was distilled off in a vacuum of a water jet pump. The product was purified by vacuum distillation, selecting the fraction with Tb = 65-73 C/0.4mm Hg. Yield: 3.5 g (60%), a liquid of a yellow color was obtained. 1H NMR (400 MHz, acetone d6; delta, ppm; J, Hz): 1.14 (t, 3H, -CH3, J = 7.1), 3.45 (q, 2H, N-CH2-CH3, J = 7.1), 3.66 (s, 4H, -N-CH2CH2-Cl), 6.63 (t, 1, p-Ar-H(-N), J = 8.9), 6.72 (d, 2, o-Ar-H(-N), J = 8.9), 7.17 (t, 2, m-Ar-H(-N), J = 8.9).
50% With thionyl chloride; In dichloromethane; for 1h;Reflux; Compound 3a was published previously.4 In brief, 2-(N-ethyl-N-phenylamino)ethanol (10g, 60mmol) in CH2Cl2 (150mL)was reacted with SOCl2 (8.8mL, 121mmol). The mixture was heated to reflux for one hour and quenched. The solvent was evaporated and the residue was purified by silica gel column chromatography to provide product (5.54g, 30mmol, 50%) as a yellow oil. 1H NMR (CDCl3, 400 MHz) delta 7.28 (m, 2H), 6.74 (m, 3H), 3.65 (m, 4H), 3.46 (q, J=7.2 Hz, 2H), 1.22 (t, J=7.2 Hz, 3H); HRMS (ESI, positive) m/z calcd. for C10H15ClN [M+H]+: 184.0893, found: 184.0836.
50% With thionyl chloride; In dichloromethane; for 1h;Reflux; 2-(N-ethyl-N-phenylamino)ethanol (10 g, 60 mmol) in CH2Cl2 (150 mL) was reacted with SOCl2 (8.8 mL, 121 mmol). The mixture was heated to reflux for one hour and quenched. The solvent was evaporated and the residue was purified by silica gel column chromatography to provide intermediate 3a (5.54 g, 30 mmol, 50%) as a yellow oil. 1H NMR (CDCl3, 400 MHz) delta 7.28 (m, 2H), 6.74 (m, 3H), 3.65 (m, 4H), 3.46 (q, J=7.2 Hz, 2H), 1.22 (t, J=7.2 Hz, 3H); HRMS (ESI, positive) m/z calcd. for C10H15ClN [M+H]+: 184.0893, found: 184.0836.
Reference： [1]Organic and Biomolecular Chemistry,2012,vol. 10,p. 5769 - 5773
[2]Macromolecules,2005,vol. 38,p. 8657 - 8663
[3]Journal of Materials Chemistry C,2015,vol. 3,p. 4545 - 4552
[4]Polymer,2018,vol. 149,p. 253 - 265
[5]ChemMedChem,2011,vol. 6,p. 869 - 875
[6]Bioorganic and Medicinal Chemistry Letters,2013,vol. 23,p. 2951 - 2954
[7]Patent: US2013/230542,2013,A1 .Location in patent: Paragraph 0125; 0152
[8]Mendeleev Communications,2018,vol. 28,p. 272 - 274
[9]Macromolecules,2004,vol. 37,p. 135 - 146
[10]Journal of the American Chemical Society,1944,vol. 66,p. 1640
[11]Journal of the Chemical Society,1944,p. 489,491
  • 2
  • [ 92-49-9 ]
  • [ 66943-05-3 ]
  • [ 222020-15-7 ]
Reference： [1]Journal fur Praktische Chemie (Weinheim),1999,vol. 341,p. 20 - 28
  • 3
  • [ 92-49-9 ]
  • [ 29654-55-5 ]
  • [ 654050-45-0 ]
YieldReaction ConditionsOperation in experiment
30% With potassium carbonate; potassium iodide; In acetone; at 56℃; for 48h;Inert atmosphere; A mixture of N-ethyl-N- (2-chloroethyl)aniline (4.04 g, 0.022 mol), 3,5-dihydroxybenzyl alcohol (1.40 g, 0.010 mol), anhydrous potassium carbonate (10 g), potassium iodide (0.5 g) and 30 mL of acetone was heated at 56 C under an argon atmosphere with intense stirring for 48 h. The reaction mixture was poured into 500mL of water, the product was extracted with CH2Cl2 (20 mL). The extract was concentrated to 5 mL and precipitated with petroleum ether. The precipitate was filtered off and dried at 70 C in a vacuum oven for 48 h and purified by recrystallization. Yield 1.3 g (30%), transparent crystals were obtained, Tm = 110 C (toluene). 1H NMR (400 MHz, acetone d6; delta, ppm; J, Hz): 1.21 (t, 6H, -CH3, J = 7.0), 3.48 (m, 4H, N-CH2-CH3), 3.71 (t, 4H, N-CH2CH2-O, J = 7.1), 4.11 (t, 4H, N-CH2CH2-O, J = 5.9), 4.59 (s, 2H, Ar-CH2-OH), 6.32 (s, 1H, p-Ar-H(CH2OH)), 6.47 (s, 2H, o-Ar-H(CH2OH)), 6.78 (t, 2H, p-Ar-H(N), J 7.3), 6.94 (d, 4H, o-Ar-H(N), J 7.9), 7.28 (t, 4H, m-Ar-H(N), J 7.3).
Reference： [1]Polymer,2018,vol. 149,p. 253 - 265
[2]Mendeleev Communications,2018,vol. 28,p. 272 - 274
[3]Macromolecules,2004,vol. 37,p. 135 - 146

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