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Volume 2003
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10.3390/M341
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Short Note

Methyl 2-Amino-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carboxylate

by
Abdullah Mohamed Asiri
Chemistry Department, Faculty of Science, King Abdul-Aziz University, Jeddah 21589, P.O. Box 80203, Saudi Arabia
Molbank 2003, 2003(3), M341; https://doi.org/10.3390/M341
Submission received: 5 March 2003 / Accepted: 4 June 2003 / Published: 21 June 2003
Versions Notes

Molbank 2003 m341 i001
To a mixture contaning cyclopentanone (8.49 g, 0.1 mol), methyl cyanoacetate (10.0 g, 0.1 mol) and sulfur (3.21 g, 0.1 mol) in methanol (20 ml), morpholine (10 ml) was added dropwise over a period of 30 minutes at 35 °C. The reaction mixture was heated at 45 °C with stirring for 3 hrs, then was allowed to cool to room temperature. The precipated powder was filtered and washed with ethanol (2x30 ml). Recrystallization from ethanol gave pale yellow powder (13.0g, 65 %).
M.p. 185-186°C (Ethanol, uncorrected).
IR (KBr) (cm-1; KBr Disk) 3410, 3293 (NH), 1652 (C=O), 1596 (NH), 1351 (C-N).
1H-NMR (400 MHz; CDCl3; Me4Si, δH): 2.31 (2H, m, CH2CH2CH2), 2.71 (2H, t, J = 6.70 Hz, CH2CH2CH2), 2.2.8 (2H, t, J = 7.00 Hz, CH2CH2CH2), 3.78 (3H, s, CH3O), 5.87 (2H, bs, NH2).
13C-NMR (dC): 26.12 (CH2CH2CH2), 27.82 (CH2CH2CH2), 29.66 (CH2CH2CH2), 49.56 (CH3O), 99.66, 119.16, 141.01, 164.98, 166.99 (CO).
Elemental Analysis: Calculated for C9H13NO2S (199.27): C 54.25 %, H 6.58 %, N 7.03 %, S 16.09 %; found: C 54.11 %, H 6.46 %, N 7.03 %, S 15.89 %.

Supplementary materials

Supplementary File 1Supplementary File 2Supplementary File 3

References

  1. Gewald, K.; Schinke, E.; Böttcher, H. Chem Ber. 1966, 99, 94–100.
  2. Gewald, K.; Neumann, G. Chem Ber. 1968, 101, 1933–1939.
  • Sample availability: available from the author.

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MDPI and ACS Style

Asiri, A.M. Methyl 2-Amino-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carboxylate. Molbank 2003, 2003, M341. https://doi.org/10.3390/M341

AMA Style

Asiri AM. Methyl 2-Amino-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carboxylate. Molbank. 2003; 2003(3):M341. https://doi.org/10.3390/M341

Chicago/Turabian Style

Asiri, Abdullah Mohamed. 2003. "Methyl 2-Amino-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carboxylate" Molbank 2003, no. 3: M341. https://doi.org/10.3390/M341

APA Style

Asiri, A. M. (2003). Methyl 2-Amino-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carboxylate. Molbank, 2003(3), M341. https://doi.org/10.3390/M341

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