ethyl 2-((ethoxycarbonyl)amino)-4-methyl-5-(4-nitrophenyl)thiophene-3-carboxylate synthesis
- Product Name:ethyl 2-((ethoxycarbonyl)amino)-4-methyl-5-(4-nitrophenyl)thiophene-3-carboxylate
- CAS Number:308831-93-8
- Molecular formula:C17H18N2O6S
- Molecular Weight:378.4
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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