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Chemical Structure| 15050-24-5

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Product Details of [ 15050-24-5 ]

CAS No. :15050-24-5
Formula : C10H10ClNO3
M.W : 227.64
SMILES Code : O=C(OCC1=CC=CC=C1)NCC(Cl)=O

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Application In Synthesis of [ 15050-24-5 ]

* 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 [ 15050-24-5 ]

[ 15050-24-5 ] Synthesis Path-Downstream   1~3

  • 1
  • [ 15050-24-5 ]
  • [ 2011-66-7 ]
  • [ 76337-80-9 ]
  • 2
  • [ 15050-24-5 ]
  • [ 43156-47-4 ]
  • [ 60854-64-0 ]
YieldReaction ConditionsOperation in experiment
In N-methyl-acetamide; N-Benzyloxycarbonylglycyl chloride (40.0 g.; freshly prepared as hereinbefore described) was dissolved in dry dimethylformamide (50 ml.) and the solution was added to a solution of 3-amino-4-nitrodiphenyl thioether (24.6 g.; prepared as hereinbefore described in Example 1) in dry dimethylformamide (250 ml.). The mixture was stirred for one hour at below 35° C. and was then poured into water (1 liter). The resulting oil solidified on scratching. The solid was filtered off and recrystallized from ethanol, to give 3-(2-benzyloxycarbonylaminoacetamido)-4-nitrodiphenyl thioether (27.7 g.), m.p. 117°-120° C.
  • 3
  • [ 15050-24-5 ]
  • [ 1022-13-5 ]
  • [ 29176-44-1 ]
YieldReaction ConditionsOperation in experiment
6.51 g With potassium hydrogencarbonate; In chloroform; water; at -5 - 20℃; for 17h; Next, the acid chloride was added dropwise to a second flask containing 5-chloro-2-methylaminobenzophenone (3, 4.01 g, 16.32 mmol), KHC03 (16.81 g, 168.10 mmol), CHC13 (120 mL), and water (150 mL) at -5 °C. The reaction mixture was stirred for 1 h at the same temperature and 16 h at room temperature. Thin layer chromatography indicated complete consumption of the starting material. The organic phase was separated and the aqueous phase was extracted with CHC13 (2 x 100 mL). The combined organic fractions were dried over Na2S04, filtered, and evaporated in vacuo. The crude residue was purified by flash column chromatography (silica gel, 0-50percent ethyl acetate in hexanes) to give 4 (6.51 g, 91percent) as brown gum. The presence of rotamers precluded a comprehensive assignment of all proton and carbon resonances. Rf 0.50 (hexanes/ethyl acetate, 1 : 1); NMR (400 MHz, CDC13) delta 7.76 (t, J= 8.7 Hz, 2H), 7.62 (t, J= 7.4 Hz, 0.83H), 7.57 (dt, J= 10.0, 3.5 Hz, 1H), 7.53-7.40 (m, 3.36H), 7.32 (dd, J= 8.2, 6.3 Hz, 5.82H), 7.21 (d, J= 8.5 Hz, 0.25H), 5.62 (t, J= 4.5 Hz, 0.69H), 5.53 (s, 0.2H), 5.07 (s, 2H), 3.83 (dd, J= 17.2, 5.5 Hz, 1H), 3.70 (dd, J= 16.9, 3.7 Hz, 1H), 3.24 (s, 0.63H), 3.05 (s, 2.38H); 13C NMR (100 MHz, CDC13) delta 194.58, 193.48, 168.82, 156.27, 140.28, 139.03, 138.81, 138.26, 136.63, 136.50, 135.96, 134.76, 134.42, 133.61, 133.07, 132.51, 132.09, 131.16, 130.19, 130.08, 129.07, 128.63, 128.17, 66.95, 43.64, 38.08, 37.67; HRMS (ESI+) calculated for C24H21CIN2O4 [M + Na+] 459.1082, found 459.1068.
 

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