Practical phase-transfer synthesis of N-(ethoxycarbonyl)phthalimide and its analogues

Synthetic Communications

Volumn 27, Issue 12, 1997, Pages 2081-2086

  Siedlecka, Renata ^a   Skarzewski, Jacek ^a  

^a WROCLAW UNIVERSITY OF TECHNOLOGY   (Poland)

Author keywords

[No Author keywords available]

Indexed keywords

CHLOROFORMIC ACID ETHYL ESTER; N (ETHOXYCARBONYL)PHTHALIMIDE; PHTHALIMIDE DERIVATIVE; TETRABUTYLAMMONIUM; UNCLASSIFIED DRUG;

ARTICLE; CONFORMATIONAL TRANSITION; DRUG ACETYLATION; DRUG CONFORMATION; DRUG SYNTHESIS; PHASE TRANSITION;

EID: 0031008211     PISSN: 00397911     EISSN: None     Source Type: Journal    
DOI: 10.1080/00397919708006814     Document Type: Article

References (13)

1. Greene, T. W.; Wuts, P. G. M. Protective Groups in Organic Synthesis, Wiley, New York, 1991, p. 358.
2. Nefkens, G. H. L.; Tesser, G. L.; Nivard, R. J. F. Rec. Trav. Chim. 1960, 79, 688.
3. Worster, P. M.; Lenzoff, C. C.; McArthur, C. R. J. Org. Chem. 1980, 45, 174.
4. Santaniello, E.; Ponti, F. Synth. Comm. 1980, 10, 611.
5. Tsubouchi, H.; Tsuji, K.; Ishikawa, H. Synlett 1994, 63.
6. Siedlecka, R.; Skarzewski, J. Synlett 1996, 757; Skarzewski, J., Gupta, A. in preparation.
7. Siedlecka, R.; Skarzewski, J. Synlett 1996, 757; Skarzewski, J., Gupta, A. in preparation.
8. The observed stability of 1 depends on its structure, namely for both nitrosubstituted derivatives (1 d and e) their half-life at r.t. is about 2 months, 1 a decomposes in ca. 5% during this time, while dichloro-derivative 1 g does not show any decomposition when stored for 5 months. Moreover, 1 f undergoes spontaneous retro Diels-Alder reaction with the half-life of 5 months at r.t.
9. 9 For confirmation, water was added to pure potassium phthalimide and the reaction with ethyl chloroformate gave again ethyl 2-cyanobenzoate in 60% yield. On the other hand, the high yield of standard N-alkylation product obtained from potassium phthalimide of this batch suggests that only up to 20% of this compound was hydrolyzed, so the cyanoester formed may also result from the alcoholysis of phthalimide initiated by the impurity.
10. Sauers, C. K.; Cotter, R. J. J. Org. Chem. 1961, 26, 6.
11. Salzberg, P. L.; Supniewski, J. V. Org. Synth. Coll., Vol. I, 1946, p.119.
12. Basterfield, S.; Wilson, C. V.; Greig, M. E. Can. J. Chem. 1931, 4, 361.
13. Carrion, J. P.; Deranleau, D. A.; Donzel, B.; Esko, K.; Moser, P.; Schwyzer, R. Helv. Chim. Acta 1968, 51, 459