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Chemical Structure| 209395-32-4 Chemical Structure| 209395-32-4

Structure of 209395-32-4

Chemical Structure| 209395-32-4

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Product Details of [ 209395-32-4 ]

CAS No. :209395-32-4
Formula : C7H5NO2
M.W : 135.12
SMILES Code : O=C(N1CC#C)C=CC1=O
MDL No. :MFCD12090919
InChI Key :OBYJFWVFCFYKNY-UHFFFAOYSA-N
Pubchem ID :10214393

Safety of [ 209395-32-4 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H315-H319
Precautionary Statements:P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313

Application In Synthesis of [ 209395-32-4 ]

* 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 [ 209395-32-4 ]

[ 209395-32-4 ] Synthesis Path-Downstream   1~2

  • 1
  • [ 108-31-6 ]
  • [ 557-24-4 ]
  • [ 2450-71-7 ]
  • [ 209395-32-4 ]
YieldReaction ConditionsOperation in experiment
With sodium acetate; In water; acetic anhydride; acetic acid; Example 14 N-propargylmaleimide (22): A solution of maleic anhydride (19, 2.5 g, 25.5 mmol) and propargylamine (20, 1.75 mL, 25.5 mmol) in glacial acetic acid (50 mL) was stirred in the dark overnight. The reaction mixture was concentrated to dryness and the residue was recrystallized from a mixture of isopropyl alcohol and water. This gave 21 (3.079 g, 20.1 mmol, 79%) as white crystals. Compound 21 (1.49 g, 9.70 mmol) was suspended in acetic anhydride (7 mL) and sodium acetate (437 mg, 5.33 mmol) was added. The resulting suspension was stirred at 65 C. for 2 h, cooled down to room temperature, and then poured into ice-cold water (75 mL). The aqueous solution was extracted three times with diethyl ether. The combined organic layers were dried over Na2SO4, filtered, and concentrated. Column chromatography (CH2Cl2/EtOAc=1/1) provided 22 (755 mg, 5.59 mmol, 58%) as an off-white solid. 1H NMR (400 MHz, CDCl3) delta: 2.21 (t, 1H, J=2.6 Hz, ?C-H), 4.30 (d, 2H, J=2.6 Hz, CH2), 6.76 (s, 2H, =C-H).
  • 2
  • [ 55750-49-7 ]
  • [ 15430-52-1 ]
  • [ 209395-32-4 ]
YieldReaction ConditionsOperation in experiment
1.24 g With sodium hydrogencarbonate; at 20℃;Cooling with ice; A solution of 1.08 grams of propargylamine hydrochloride in 50 ml of saturated sodium bicarbonate was cooled with an ice water bath, and 2.0 grams of <strong>[55750-49-7]N-carboethoxymaleimide</strong> were added portionwise over a few minutes. The reaction was stirred in the cold for 30 min., then while warming to room temperature over 25 min. The reaction was then extracted with 3*25 ml of dichloromethane, which was dried over sodium sulfate, filtered and concentrated. The residue was taken up in 10 ml of ethyl acetate and heated at 50 C. for two hours to complete the cyclization. The reaction was concentrated and the residue was which was subjected to flash column chromatography on silica gel with 30% ethyl acetate in hexane. A second chromatography as before gave 1.24 g of the product as a very light yellow oil. NMR (CDCl3): delta 6.77 (s, 2H, CHC=O), 4.30 (d, 2H, NCH2, J=2.4 Hz), 2.22 (t, 1H, CCH, J=2.5 Hz).
 

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