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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 30, 2000 - Issue 3
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Original Articles

The First Synthesis of N-Alkyl-N-Arylthiocarbamoylacetates and Acetic Acids

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Pages 565-574 | Received 26 Apr 1999, Published online: 04 Dec 2007

References

  • Ogino , T. , Tsuji , K. , Tojo , T. , Igari , N. , Seki , N. , Sudo , Y. , Manda , T. , Nishigaki , F. and Matsuo , M. 1998 . Bioorg. Med. Chem. Lett. , 8 : 75 – 80 .
  • Matsuo , M. , Tsuji , K. , Spears , G. W. , Ogino , T. , Nishimura , H. and Tojo , T. WO . 95–24395 . [Chem. Abstr. 124 117102e (1995)]. 3. All new compounds reported herein showed satisfactory spectral data (1H-NMR, IR and MS)
  • Raap , R. 1968 . Can. J. Chem. , 46 : 2255 – 2261 .
  • Barnikow , G. and Strickmann , G. 1967 . Chem. Ber. , 100 : 1413 – 1427 .
  • Roma , G. , Ermili , A. and Balbi , A. 1975 . J. Heterocycl. Chem. , 12 : 1103 – 1109 .
  • One measure of nucleophilicity is pKa. The pKaof N-methylaniline is 4.85, while the pKaof morpholine is 8.33, a nearly 10,000 fold difference
  • Interestingly, for halogen substitution in the meta and/or para positions of the phenyl ring, the reaction proceeded smoothly, but for ortho substitution the main product was not the ethyl carbamoyl acetate, but apparently a cyclized product lacking the halogen (unpublished results, T. Tojo, G. Spears)
  • Meth-Cohn , O. and Narine , B. 1980 . Synthesis , : 133 – 5 .
  • Steinkopf , W. 1914 . Ann. , 403 : 17 – 44 .
  • Paul , D. and Haberfield , P. 1976 . J. Org. Chem. , 41 : 3170 – 3175 .
  • Zassignment , E. , Conde , S. , Corral , C. and Lissavetzky , J. 1985 . J. Heterocyl. Chem. , 22 : 301 – 304 . It was important to use the pure E isomer for the next reaction because the isomeric N-methyl-2-thiophenecarboxamide obtained from the Z-isomer was very difficult to separate from the desired product.

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