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Chemical Structure| 6191-99-7 Chemical Structure| 6191-99-7

Structure of 3-Ethoxy-acryloyl chloride
CAS No.: 6191-99-7

Chemical Structure| 6191-99-7

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Product Details of [ 6191-99-7 ]

CAS No. :6191-99-7
Formula : C5H7ClO2
M.W : 134.56
SMILES Code : O=C(Cl)C=COCC
MDL No. :MFCD09029675
InChI Key :SFMFACMIOWQIPR-ONEGZZNKSA-N
Pubchem ID :5325500

Safety of [ 6191-99-7 ]

GHS Pictogram:
Signal Word:Danger
Hazard Statements:H225-H302-H314-H317-H334
Precautionary Statements:P210-P261-P280-P301+P312-P305+P351+P338-P310
Class:8(3)
UN#:2920
Packing Group:

Application In Synthesis of [ 6191-99-7 ]

* 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 [ 6191-99-7 ]

[ 6191-99-7 ] Synthesis Path-Downstream   1~5

  • 1
  • [ 6191-99-7 ]
  • [ 16618-68-1 ]
  • [ 917833-39-7 ]
YieldReaction ConditionsOperation in experiment
With pyridine; at 0 - 20℃; for 0.5h; To 14 mL of a pyridine solution containing 1.4 g of <strong>[16618-68-1]3-bromo-5-methoxyaniline</strong>, 1.0 g of (2E)-3-ethoxyacryloyl chloride was added under cooling with ice, and the mixture was stirred at room temperature for 30 minutes. The reaction mixture was fed into ice water, and the precipitate was collected by filtration. Ethyl acetate and water were added thereto, and the resultant solution was adjusted to pH 4.0 with 1 mol/L hydrochloric acid. The organic layer was separated, and the aqueous layer was extracted with ethyl acetate. The organic layer and the extract were combined, and the resultant solution was washed sequentially with water and an aqueous saturated sodium chloride solution and dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure to obtain 1.7 g of a light brown solid, (2E)-N-(3-bromo-5-methoxyphenyl)-3-ethoxyacrylamide. 1H-NMR (CDCl3) delta: 1.26 (3H, t, J=7.1 Hz), 3.79 (3H, s), 3.96 (2H, q, J=7.1 Hz), 5.28 (1H, d, J=12.1 Hz), 6.79 (1H, t, J=1.9 Hz), 6.87 (1H, s), 7.20 (1H, t, J=1.9 Hz), 7.24 (1H, t, J=1.9 Hz), 7.63 (1H, d, J=12.1 Hz)
  • 2
  • [ 6191-99-7 ]
  • [ 87-63-8 ]
  • [ 863127-76-8 ]
YieldReaction ConditionsOperation in experiment
73.6% With pyridine; In tetrahydrofuran; at 0 - 20℃; for 2h; To a cold stirring solution of 2-chloro-6-methylaniline (59.5 g 0.42 mol) and pyridine (68 ml, 0.63 mol) in THF (600 mL) was added 3-ethoxyacryloyl chloride (84.7 g, 0.63 mol) slowly keeping the temp at 0-5C. The mixture was then warmed and stirred for 2 h. at 20C. Hydrochloric acid (1N, 115 mL) was added at 0-10C. The mixture was diluted with water (310 mL) and the resulting solution was concentrated under vacuum to a thick slurry. The slurry was diluted with toluene (275 mL) and stirred for 15 min. at 20-22C then 1 h. at 0C. The solid was collected by vacuum filtration, washed with water (2 x 75 mL) and dried to give 74.1 g (73.6 % yield) of (E)-N-(2-chloro-6-methylphenyl)-3-ethoxyacrylamide). lH NMR (400 Hz, DMSO-d6) 8 1. 26 (t, 3H, J= 7 Hz), 2.15 (s, 3H), 3.94 (q, 2H, J= 7 Hz), 5.58 (d, 1H, J=12.4 Hz), 7.10-7. 27 (m, 2H, J=7.5 Hz), 7.27-7. 37 (d, 1H, J=7.5 Hz), 7.45 (d, 1H, J=12.4 Hz), 9. 28 (s, 1H) ; l3c NMR (100MHz, CDC13) b : 14. 57, 18.96, 67.17, 97.99, 126. 80, 127. 44, 129. 07, 131.32, 132.89, 138. 25,161. 09,165. 36.
300 g With pyridine; In tetrahydrofuran; at 10 - 30℃; for 4h; Ethyl vinyl ether compound of formula-5 (500 gm) was slowly added to oxalyl chloride compound of formula-4 (670 ml) at 10-15C. Raised the temperature of the reaction mixture to 25-30C and stirred for 12 hours at the same temperature. Heated the reaction mixture to 120- 125C and stirred for 90 minutes at the same temperature. Cooled the reaction mixture to 30-35 C and (E)-3-ethoxyacryloyl chloride compound of formula-7 was collected by fractional distillation. Added tetrahydrofuran (1160 ml) to the obtained compound of formula-7 and cooled the reaction mixture to 10-15C. Slowly added a solution of 2-methyl-6-chloroaniline compound of formula-9 (290 gm), pyridine (248ml) & tetrahydrofuran (1160 ml) to the reaction mixture at same temperature. Raised the temperature of the reaction mixture to 25-30C and stirred the reaction mixture for 4 hours at the same temperature. Cooled the reaction mixture to 5-10C and acidified the reaction mixture using aqueous HC1 solution. Water and ethyl acetate were added to the reaction mixture and stirred for 10 minutes. Separated the both aqueous & organic layers and extracted the aqueous layer with ethyl acetate. Washed the total organic layer with aqueous sodium bicarbonate solution followed by with water. Distilled off the solvent completely from the organic layer under reduced pressure. Ethyl acetate was added to the obtained compound at 25-30C and cooled the reaction mixture to 0-5C. Stirred the reaction mixture for 2 hours at the same temperature. Filtered the precipitated solid, washed with chilled ethyl acetate and dried the material to get the title compound. Yield: 300 gm; M.R.: 160-164C; HPLC Purity: 99.66%.
  • 3
  • [ 6191-99-7 ]
  • [ 2339-58-4 ]
  • C12H14FNO3 [ No CAS ]
  • 4
  • [ 6191-99-7 ]
  • [ 87-63-8 ]
  • [ 863127-76-8 ]
YieldReaction ConditionsOperation in experiment
With pyridine; In tetrahydrofuran; at 20℃; Example 1; [0163] A mixture of ethyl beta-ethoxyacrylate (26.50 g, 183 rnmol) and 2 N sodium hydroxide(110 mL, 220 mrnol) was refluxed for 2 h and cooled to 0C , water was removed under vacc, and the yellow solids were triturated with toluene and evaporated to give the sodium beta- ethoxyacrylate (25 g, 97%). The mixture of sodium beta-thoxyacrylate (10.26 g, 74.29 mrnol) and thionyl chloride (25 mL, 343 mmol) was refluxed for 2 h, and evaporated, to give the beta- ethoxyacryloyl chloride crude product, which was used without purification, To a cold stirring solution of 3-ethoxyacryloyl chloride in THF (100 mL) was added 2-chloro-6-methylaniline (6.2 mL, 50,35 mmol) and pyridine (9 ml, 1 1 1 mmol) The mixture was then wanned and stirred overnight at room temperature. Water was added at 0-10C, extracted with EtOAc, The organic layer was washed with CuSO4 (3x50 mL) and the resulting solution was passed a pad of silica gel, concentrated under vacuum to give solids, The solids was diluted with toluene and kept, at 0C, The solid was collected by vacuum filtration, washed with water and dried to give 5,2 g (43% yield) of compound 1 , (E)-N-(2-chloro-6-methylphenyl)-3-ethoxyacrylamide). 1H NMR (500 Hz1 CDCl3) delta 1 ,26 (t, 3H1 J=7 Hz), 2, 15 (s, 3H), 3 94 (q, 2H, J=7 Hz), 5,58 (d, IH, J=12.4 Hz), 7.10-7.27 (m, 2H, J=7.5 Hz), 7,27-7.37 (d, IH, J=7.5 Hz), 7,45(d, 1Hf J=12.4 Hz); ESI-MS: calcd for (Cl 2H14C1NO2) 239, found 240 MH+),
With pyridine; In tetrahydrofuran; at 20℃; Example 1[0156] A mixture of ethyl beta-ethoxyacrylate (26.50 g, 183 mmol) and 2 N sodium hydroxide (110 mL, 220 mmol) was refluxed for 2 h and cooled to 0 C water was removed under vacc, and the yellow solids were triturated with toluene and evaporated to give the sodium beta-ethoxyacrylate (25 g, 97%). The mixture of sodium beta-thoxyacrylate (10.26 g, 74.29 mmol) and thionyl chloride (25 mL, 343 mmol) was refluxed for 2 h, and evaporated, to give the beta-ethoxyacryloyl chloride crude product, which was used without purification. To a cold stirring solution of 3-ethoxyacryloyl chloride in THF (100 mL) was added 2-chloro-6- methylaniline (6.2 mL, 50.35 mmol) and pyridine (9 ml, 111 mmol). The mixture was then warmed and stirred overnight at room temperature. Water was added at 0-10 C, extracted with EtOAc. The organic layer was washed with CuSO4 (3x50 mL) and the resulting solution was passed a pad of silica gel, concentrated under vacuum to give solids. The solids was diluted with toluene and kept, at O0C. The solid was collected by vacuum filtration, washed with water and dried to give 5.2 g (43% yield) of compound 1, (E)-N-(2-chloro-6- methylphenyl)-3-ethoxyacrylamide). 1H NMR (500 Hz, CDCl3) delta 1.26 (t, 3H, J=7 Hz), 2.15 (s, 3H), 3.94 (q, 2H, J=7 Hz), 5.58 (d, IH, J=12.4 Hz), 7.10-7.27 (m, 2H, J=7.5 Hz), 7.27- 7.37 (d, IH, J=7.5 Hz), 7.45(d, IH, J=12.4 Hz); ESI-MS: calcd for (C12Hi4ClNO2) 239, found 240 MH+).
 

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