N-3-thienylacetamide Chemical Properties

Melting point:

147-148 °C

Boiling point:

325.0±15.0 °C(Predicted)

Density 

1.260±0.06 g/cm3(Predicted)

storage temp. 

2-8°C(protect from light)

form 

Pale yellow flakes

pka

14.96±0.70(Predicted)

Appearance

Light green to green Solid

Safety Information

HS Code 

2934999090

N-3-thienylacetamide Usage And Synthesis

Synthesis

3-Aminothiophene (1.08 g, 10.9 mmol) was dissolved in ethanoic anhydride (20 mL) and the reaction was stirred for 3 hours at room temperature. After the reaction was completed, water (50 mL) was added and stirring was continued for 30 minutes. Subsequently, the pH was adjusted to >9 by slowly adding 4 M aqueous sodium hydroxide (150 mL). the reaction mixture was extracted with dichloromethane (3 x 100 mL). The organic phases were combined, washed with brine (30 mL), dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was crystallized by dichloromethane/petroleum ether mixed solvent to afford N-(3-thienyl)acetamide (994 mg, 65% yield) as a white crystalline solid. The structure of the product was confirmed by 1H-NMR (500 MHz, CDCl3) and 13C-NMR (125 MHz, CDCl3): 1H-NMR δ 2.17 (s, 3H, CH3), 7.00 (dd, J = 5.0, 1.3 Hz, 1H, Ar-H), 7.23 (dd, J = 5.0, 3.2 Hz, 1H, Ar-H) 7.45 (br, 1H, N-H), 7.55 (dd, J = 3.2, 1.3 Hz, 1H, Ar-H); 13C-NMR δ 18.64 (CH3), 105.03, 115.64, 119.26, 130.27 (Arom-C), 162.11 (C=O).

References

[1] Patent: US2009/247579, 2009, A1. Location in patent: Page/Page column 44
[2] Patent: WO2015/66371, 2015, A1. Location in patent: Paragraph 00478-00479

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