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ChemicalBook CAS DataBase List ethyl 2-((ethoxycarbonyl)amino)-4-methyl-5-(4-nitrophenyl)thiophene-3-carboxylate
308831-93-8

ethyl 2-((ethoxycarbonyl)amino)-4-methyl-5-(4-nitrophenyl)thiophene-3-carboxylate synthesis

3synthesis methods
174072-89-0 Synthesis
Ethyl 2-amino-4-methyl-5-(4-nitrophenyl)thiophene-3-carboxylate

174072-89-0
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ethyl 2-((ethoxycarbonyl)amino)-4-methyl-5-(4-nitrophenyl)thiophene-3-carboxylate

308831-93-8
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Yield:308831-93-8 79%

Reaction Conditions:

in toluene

Steps:

R.9 Ethyl 2-ethoxycarbonylamino-4-methyl-5-(4-nitrophenyl)thiophene-3-carboxylate
Reference Example 9 Ethyl 2-ethoxycarbonylamino-4-methyl-5-(4-nitrophenyl)thiophene-3-carboxylate The compound obtained in Reference Example 1 (500 mg, 1.63 mmol) was dissolved in toluene (9 ml) followed by addition of ethyl chloroformate (0.19 ml, 1.96 mmol), and the mixture was heated under reflux for 5 hours. After cooling, the reaction mixture was concentrated under reduced pressure. The residue was chromatographed on silica gel to give the title compound as yellow powder (90 mg, 79%). mp: 130-131° C. (recrystallized from ethyl acetate-hexane). 1H-NMR (200 MHz, CDCl3) δ: 1.35 (3H, t, J=7.1 Hz), 1.42 (3H, t, J=7.2 Hz), 2.42 (3H, s), 4.31 (2H, q, J=7.1 Hz), 4.39 (2H, q, J=7.2 Hz), 7.59 (2H, d, J=9.0 Hz), 8.27 (2H, d, J=9.0 Hz), 10.66 (1H, s). IR (KBr): 1740, 1665, 1597, 1557, 1533, 1516, 1352,1257 cm-1.

References:

Takeda Chemical Industries, Ltd. US6297379, 2001, B1

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ethyl 2-((ethoxycarbonyl)amino)-4-methyl-5-(4-nitrophenyl)thiophene-3-carboxylate Related Search:

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