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[ CAS No. 55750-49-7 ]

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2D
Chemical Structure| 55750-49-7
Chemical Structure| 55750-49-7
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Product Details of [ 55750-49-7 ]

CAS No. :55750-49-7MDL No. :MFCD16619570
Formula :C7H7NO4Boiling Point :257.3±23.0°C at 760 mmHg
Linear Structure Formula :-InChI Key :XUXSQROIUORWRI-UHFFFAOYSA-N
M.W :169.14Pubchem ID :319934
Synonyms :

Computed Properties of [ 55750-49-7 ]

TPSA : 63.7 H-Bond Acceptor Count : 4
XLogP3 : 0 H-Bond Donor Count : 0
SP3 : 0.29 Rotatable Bond Count : 2

Safety of [ 55750-49-7 ]

Signal Word:WarningClassN/A
Precautionary Statements:P280UN#:N/A
Hazard Statements:H302-H317Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 55750-49-7 ]

  • Upstream synthesis route of [ 55750-49-7 ]
  • Downstream synthetic route of [ 55750-49-7 ]

[ 55750-49-7 ] Synthesis Path-Upstream   1~1

  • 1
  • [ 541-59-3 ]
  • [ 541-41-3 ]
  • [ 55750-49-7 ]
YieldReaction ConditionsOperation in experiment
50% With 4-methyl-morpholine In water; ethyl acetate 1)
Ethyl-2,5-dioxo-2,5-dihydro-1H-pyrrole-1-carboxylate
9.7 g (0.1 mol) of maleimide are solubilized in 50 ml of ethyl acetate and 1.1 ml of N-methylmorpholine at 5° C.
1.1 ml of ethyl chloroformate are added dropwise.
The mixture is stirred for 1/2 hour.
The insoluble material is removed by filtration.
The filtrate is washed with 50 ml of water.
The organic phase is dried over MgSO4 and is then concentrated under vacuum.
The oil obtained is purified on Merck Geduran.(R). silica gel (40-63 μm). Elution: CH2Cl2/ACOEt 66/34.
16.9 g are isolated with a yield of 50percent.
Mass spectrum: M/z=170.1 (ES+) theoretical M=169
41% With triethylamine In N,N-dimethyl-formamide at 0 - 20℃; for 4.00 h; Ethyl chloroformate (0.38 ml, 4 mmol) was added dropwise to a stirred solution maleimide (0.3 g, 3 mmol) and triethylamine (0.5 ml, 3.5 mmol) in dimethylformamide (2 ml) at 0-5° C.
The reaction mixture was allowed to warm to room temperature and stand for 4 h.
Methyl alcohol (1 ml) was added, diluted with chloroform (20 ml) and washed with water (3*10 ml).
The chloroform solution was dried (Na2SO4) and concentrated in vacuum.
The residue was purified in chloroform and hexane on a silica gel column to give N-ethoxycarbonyl-maleimide (yield 41percent).
1H NMR (CDCl3) δ 1.34 (3H, t, CH3), 4.27 (2H, q, CH2), 6.21 (1H, d, CH=), 6.72 (1H, d, CH=).
Reference: [1] Organic Letters, 2015, vol. 17, # 23, p. 5846 - 5849
[2] Chemical Communications, 2014, vol. 50, # 7, p. 859 - 861
[3] Patent: US2010/297025, 2010, A1
[4] Patent: US9273304, 2016, B2. Location in patent: Page/Page column 16
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