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Chemical Structure| 853058-40-9 Chemical Structure| 853058-40-9

Structure of 853058-40-9

Chemical Structure| 853058-40-9

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Product Details of [ 853058-40-9 ]

CAS No. :853058-40-9
Formula : C10H14N2O4
M.W : 226.23
SMILES Code : O=C(C1=C(N)C(C(OCC)=O)=CN1)OCC
MDL No. :MFCD10566518
InChI Key :JLMFCRWHSHFKAJ-UHFFFAOYSA-N
Pubchem ID :53434156

Safety of [ 853058-40-9 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302
Precautionary Statements:P280-P305+P351+P338

Application In Synthesis of [ 853058-40-9 ]

* 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.

  • Upstream synthesis route of [ 853058-40-9 ]

[ 853058-40-9 ] Synthesis Path-Upstream   1~3

  • 1
  • [ 42466-67-1 ]
  • [ 13433-00-6 ]
  • [ 853058-40-9 ]
YieldReaction ConditionsOperation in experiment
95%
Stage #1: With sodium ethanolate In ethanol at 20℃; for 20 h; Heating / reflux
Stage #2: With acetic acid In ethanol
Starting materials, can be purchased from commercial sources or prepared using literature procedures.
To a mixture of diethyl aminomalonate hydrochloride (8.0 g, 47.3 mmol) and ethyl (ethoxymethylene)cyanoacetate (10.0 g, 47.2 mmol) in ethanol (60 ml) at r.t. was added a 21 wt. percent solution of sodium ethoxide in ethanol (62 ml, 165.4 mmol).
The reaction mixture was then stirred at reflux for 20 h.
After cooling to r.t., the mixture was neutralized with AcOH (6.75 ml, 118 mmol), concentrated, diluted with H2O (250 mL) and extracted with CHCl3 (3*250 mL).
The combined organics were dried (MgSO4), filtered, concentrated and purified by flushing through a pad of silical gel (10 g, EtOAc) to yield amino pyrrole 3 (10.2 g, 45.1 mmol, 95percent) as a yellow solid. 1H NMR: (500 MHz, DMSO-d6) δ 11.55 (br s, 1H), 7.21 (d, J=4.0, 1H,), 5.57 (s, 2H), 4.21 (q, J=7.5 Hz, 2H), 4.18 (q, J=7.8 Hz, 2H), 1.27 (t, J=7.5 Hz, 2H), 1.25 (t, J=7.8 Hz, 2H); LC/MS: (ES+) m/z (M-OEt)+=181; HPLC Rt=0.96, column N.
References: [1] Patent: US2005/124623, 2005, A1, . Location in patent: Page/Page column 43.
  • 2
  • [ 144918-37-6 ]
  • [ 13433-00-6 ]
  • [ 853058-40-9 ]
YieldReaction ConditionsOperation in experiment
80% With sodium ethanolate In ethanol for 14 h; Reflux Diethyl 2-aminomalonate hydrochloride (20 g, 90 mmol) and ethyl 2-cyano-3-ethoxyacrylate (16 g, 94 mmol) were dissolved in ethanol (250 mL). Sodium ethoxide (21 g, 310 mmol) was added, and the mixture was heated to reflux for 14 hours. The mixture was neutralized with acetic acid (20 mL) and concentrated. The mixture was partitioned between dichloromethane and water. The aqueous layer was extracted twice with dichloromethane. The combined organic layers were washed with brine, dried over sodium sulfate, and concentrated. The resulting solid was triturated with a mixture of heptanes and dichloromethane (10:1) overnight. The suspension was filtered to yield 12.5g of diethyl 3-amino-lH-pyrrole-2,4-dicarboxylate as a solid (80percent yield). 1H NMR (400 MHz, DMSO-J6) δ 11.53 (s, IH), 7.20 (d, J= 4.0 Hz, IH), 5.57 (s, 2H), 4.27 - 4.11 (m, 4H), 1.32 - 1.19 (m, 6H).
References: [1] Patent: WO2011/25940, 2011, A1, . Location in patent: Page/Page column 85.
  • 3
  • [ 6829-40-9 ]
  • [ 94-05-3 ]
  • [ 853058-40-9 ]
References: [1] Patent: US6693193, 2004, B1, . Location in patent: Page column 14.
[2] Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, # 1, p. 218 - 222.
 

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