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Chemical Structure| 5112-47-0 Chemical Structure| 5112-47-0

Structure of 5112-47-0

Chemical Structure| 5112-47-0

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Product Details of [ 5112-47-0 ]

CAS No. :5112-47-0
Formula : C10H5ClO3
M.W : 208.60
SMILES Code : O=C(Cl)C1=CC(C2=CC=CC=C2O1)=O
MDL No. :MFCD11617085

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Application In Synthesis of [ 5112-47-0 ]

* 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 [ 5112-47-0 ]

[ 5112-47-0 ] Synthesis Path-Downstream   1~2

  • 1
  • [ 5112-47-0 ]
  • [ 71574-33-9 ]
  • N-(4,5-dimethylthiazol-2-yl)-4-oxo-4H-chromene-2-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
With N,N-diethyl-N-isopropylamine; In N,N-dimethyl-formamide; at 120℃; for 0.0833333h;Microwave irradiation; To a solution of chromone-2-carboxylic acid (0.5 g, 2.63 mmol) in DMF (4 mL), POCl3 (241 mul, 2.6 mmol) was added. The mixture was stirred at room temperature for 30 min, with in situ formation of the corresponding acyl chloride. Then N,N-diethylpropan-2-amine (459 mul, 2.63 mmol) and <strong>[71574-33-9]4,5-dimethylthiazol-2-amine hydrochloride</strong> (433 mg, 2.63 mmol) were added. The system was heated 120 C for 5 min in a microwave apparatus. After, the mixture was diluted with dichloromethane (20 mL), washed with H2O (2 * 10 mL) and with saturated NaHCO3 solution (2 * 10 mL). The organic phase was dried with Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by flash chromatography (50% AcOEt/n-hexane). N-(4,5-dimethylthiazol-2-yl)-4-oxo-4H-chromene-2-carboxamide as a yellow powder (Yield 40%). 1H NMR (CDCl3): delta = 2.26 (3H, s, CH3). 2.35 (3H, s, CH3), 7.27 (1H, s, H(3)), 7.44 (1H, d, J = 8.4 Hz, H(8)), 7.49 (1H, ddd, J = 8.0, 7.2, 1.0 Hz, H(6)), 7.76 (1H, ddd, J = 8.7, 7.2, 1.7 Hz, H(7)), 8.23 (1H, dd, J = 8.0, 1.5 Hz, H(5)). 13C NMR (CDCl3): delta = 11.0 (CH3), 14.3 (CH3), 113.3 (C3), 118.0 (C8), 122.0 (C3'), 124.4 (C4a), 126.2 (C5), 126.3 (C6), 134.9 (C7), 142.0 (C4'), 153.3 (C8a), 156.2 (C1'), 157.0 (C2, CONH) , 177.6 (C4). MS/EI m/z: 300 (M+?, 100), 272 (17), 199 (27), 163 (31), 139 (76), 101 (41).
  • 2
  • [ 7210-76-6 ]
  • [ 5112-47-0 ]
  • ethyl 4-methyl-2-(4-oxo-4H-chromene-2-carboxamido)thiazole-5-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
In N,N-dimethyl-formamide; at 120℃; for 0.0833333h;Microwave irradiation; To a solution of chromone-2-carboxylic acid (0.5 g, 2.6 mmol) in DMF (4 mL), POCl3 (241 μl, 2.6 mmol) was added. The mixture was stirred at room temperature for 30 min, with in situ formation the corresponding acyl chloride. Then ethyl 2-amino-4-methylthiazol-5-carboxylate (490 mg, 2.6 mmol) was added. The system was heated 120 C for 5 min in a microwave apparatus. After, the mixture was diluted with dichloromethane (20 mL), washed with H2O (2 * 10 mL) and with saturated NaHCO3 solution (2 * 10 mL). The organic phase was dried with Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by crystallization in methanol/n-hexane. The ethyl 4-methyl-2-(4-oxo-4H-chromene-2-carboxamido)thiazole-5-carboxylate was obtained as a yellow powder (Yield 43%). 1H NMR (CDCl3): 1.39 (3H, t, J = 7.1 Hz, CH2CH3), 2.70 (3H, s, CH3), 4.35 (2H, q, J = 7.1 Hz, CH2CH3), 7.32 (1H, s, H(3)), 7.58-7.46 (2H, m, H(8), H(6)), 7.80 (1H, ddd, J = 8.7, 7.2, 1.7 Hz, H(7)), 8.25 (1H, dd, J = 8.0, 1.6 Hz, H(5)), 10.22 (1H, bs, NH). 13C NMR (CDCl3): δ = 14.3 (CH2CH3), 17.0 (CH3), 61.2 (CH2CH3), 113.9 (C3), 117.7 (C3'), 118.0 (C8), 124.4 (C4a), 126.3 (C5), 126.6 (C6), 135.2 (C7), 152.2 (C4'), 155.1 (C8a), 156.2 (C1'), 157.3 (C2), 157.9 (CONH), 162.2 (COOCH2CH3), 177.4 (C4). MS/EI m/z: 357.9 (M+⩽, 100), 173 (98), 150 (49), 89 (96).
 

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