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Chemical Structure| 10314-06-4 Chemical Structure| 10314-06-4

Structure of 10314-06-4

Chemical Structure| 10314-06-4

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Product Details of [ 10314-06-4 ]

CAS No. :10314-06-4
Formula : C12H10ClNO3
M.W : 251.67
SMILES Code : O=C(Cl)CCCN(C(C1=C2C=CC=C1)=O)C2=O
MDL No. :MFCD02656536
InChI Key :STXHPGKNMJVJKL-UHFFFAOYSA-N
Pubchem ID :594886

Safety of [ 10314-06-4 ]

GHS Pictogram:
Signal Word:Danger
Hazard Statements:H302-H312-H314-H332
Precautionary Statements:P260-P261-P264-P270-P271-P280-P301+P312-P301+P330+P331-P302+P352-P303+P361+P353-P304+P340-P305+P351+P338-P310-P312-P321-P322-P330-P363-P405-P501
Class:8
UN#:3261
Packing Group:

Application In Synthesis of [ 10314-06-4 ]

* 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 [ 10314-06-4 ]

[ 10314-06-4 ] Synthesis Path-Downstream   1~2

  • 1
  • [ 628-97-7 ]
  • [ 10314-06-4 ]
  • [ 322391-58-2 ]
YieldReaction ConditionsOperation in experiment
37% Compound (15) was prepared following the procedure described in the above Scheme 1. Synthesis of ?-ketoester (32). 2.4 g (10 mmol) of 4-phthalimidoburyric acid (29) (prepared as described in G. Talbot, R. Gaudry, L. Berlinguet Can. J. Chem. 1958, 36, 593-596) was dissolved in 7.5 ml of SOCl2 and the mixture was refluxed under nitrogen for 3 hours. Excess of SOCl2 was then removed under a nitrogen flow and the resulting acid chloride (30) was used in the next step without further purification. Separately, a solution of ethyl palmitate (31) (1.47 g, 5.16 mmol) in anhydrous THF (6.5 ml) was slowly added to a 1.0 M solution of lithium bis(trimethylsilyl)amide (LHMDS) in THF (6.2 ml, 6.2 mmol) cooled at ?20 C. and the resulting mixture was stirred for additional 20 minutes. Acid chloride (30) previously prepared as described above, was dissolved in anhydrous THF (10 ml), cooled at ?20 C., and added via cannula to the solution containing (31) and LHMDS at the same temperature. The mixture was stirred at ?20 C. for 30 minutes and then at room temperature for 2 hours. The reaction was quenched with a saturated aqueous solution of ammonium chloride and extracted with ethyl acetate. The organic layer was dried over sodium sulfate and concentrated under vacuum. The crude residue was purified by silica gel column chromatography using hexane-ethyl acetate (8:2) as the eluant, to obtain 0.95 g (1.9 mmol, 37% yield) of pure ?-ketoester (32) as a colorless oil: 1H NMR (CDCl3, 200 MHz) ? 0.87 (t, 3H, J=6.4 Hz), 1.23 (t, 3H, J=7.3 Hz), 1.24 (bs, 24H), 2.05 (quintet, 2H, J=7.2 Hz), 2.24-2.34 (m, 4H), 2.51 (t, 2H, J=7.6 Hz), 3.78 (t, 1H, J=6.9 Hz), 4.12 (q, 2H, J=7.1 Hz), 7.69-7.73 (m, 2H), 7.82-7.87 (m, 2H); MS (FAB+) m/z 500 (M+H)+. Synthesis of thiouracil (15). ?-Ketoester (32) (0.12 g, 0.24 mmol) was dissolved in 2 ml of absolute ethanol. Thiourea (0.024 g, 0.33 mmol) and potassium t-butoxyde (0.028 g, 0.25 mmol) were added and the resulting mixture was refluxed for 5 hours. The mixture was then cooled to room temperature and the solvent was removed under vacuum. The residue was treated with 20 ml of water and neutralized with an aqueous solution of acetic acid 0.5 N. The product was extracted with ethyl acetate and the organic layer was washed with brine, dried over anhydrous sodium sulfate and concentrated under vacuum. The crude residue was then redissolved in 3 ml. of ethanol, treated with 0.06 ml of hydrazine monohydrate (1.3 mmol), and the mixture was refluxed overnight. The resulting suspension was cooled to room temperature. The white solid was collected by filtration, washed with small portions of ethyl acetate, and dried under vacuum, to give 51 mg (0.13 mmol, 54% yield) of product (15): m.p. 123-125 C.; 1H NMR (CDCl3, 200 MHz) ? 0.88 (t, 3H, J=6.4 Hz), 1.26 (bs, 24H), 1.77 (m, 2H), 2.29-2.45 (m, 6H), 8.87 (bs, 1H), 9.19 (bs, 1H); MS (FAB+) m/z 381 (M+H)+.
  • 2
  • [ 10314-06-4 ]
  • [ 57497-39-9 ]
  • C16H20N2O4 [ No CAS ]
 

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