N,N′-Dichloro bis(2,4,6-trichlorophenyl)urea (CC-2): an efficient reagent for the synthesis of α-chloro-nitroso compounds

Tetrahedron Letters

Volumn 48, Issue 5, 2007, Pages 767-770

  Gupta, A K ^a   Acharya, J ^a   Pardasani, D ^a   Dubey, D K ^a  

^a Vertox Lab   (India)

Author keywords

Chloro nitroso alkanes; Bis (2,4,6 trichlorophenyl)urea; CC 2; N,N Dichloro bis(2,4,6 trichlorophenyl)urea; Oximes; tert Butyl hypochlorite

Indexed keywords

ALPHA CHLORONITROSO DERIVATIVE; CARBANILAMIDE DERIVATIVE; N,N' DICHLORO BIS(2,4,6 TRICHLOROPHENYL)UREA; NITROSO DERIVATIVE; REAGENT; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION KINETICS; ORGANIC CHEMISTRY; REACTION OPTIMIZATION; RECYCLING; SYNTHESIS;

EID: 33846003545     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2006.12.001     Document Type: Article

References (35)

1. Cecherelli P., Curini M., Epifano F., Marcotullio M.C., and Rosati O. Tetrahedron Lett. 39 (1998) 4385
2. Tordeux M., Boumizane K., and Wakselman C. J. Org. Chem. 58 (1993) 1939
3. Sabuni M., Kresz G., and Braun H. Tetrahedron Lett. 25 (1984) 5377
4. Walters T.R., Zajac Jr. W., and Woods J.M. J. Org. Chem. 56 (1991) 316
5. Yamamoto M., and Momiyama N. Chem. Commun. (2005) 3514
6. Martynov I.V., Chepakova L.A., Brel V.K., and Sokolov V.B. Zh. Obshch. Khim. 56 (1986) 2020
7. Kruglyak Yu.L., Landau M.A., Leibovskaya G.A., Martynov I.V., and Saltykova L.I. Zh. Obshch. Khim. 41 (1971) 2338
8. Kayen A.H.M., and De Boer Th. Recl. Trav. Chim. Phys. Bas. 96 (1977) 8
9. Archibald T.G., Garver L.G., Baum K., and Cohen M.C. J. Org. Chem. 54 (1989) 2869
10. Labaziewicz H.L., and Riddell F.G. J. Chem. Soc., Perkin Trans. 1 (1979) 2926
11. Diekmann H., and Luttke W. Angew. Chem., Int. Ed. Engl. 7 (1968) 388
12. Barnes M.W., and Patterson J.M. J. Org. Chem. 41 (1976) 733
13. Kugelman M., Mallams A.K., and Vernay H.F. J. Chem. Soc., Perkin Trans. 1 (1976) 1113
14. Bozzi E.G., Shiue Ch.Y., and Clapp L.B. J. Org. Chem. 38 (1973) 56
15. Diekmann H., and Luttke W. Angew. Chem., Int. Ed. Engl. 7 (1968) 387
16. Corey E.J., and Estreicher H. Tetrahedron Lett. 21 (1980) 1117
17. Felber H., Kresze G., Brau H., and Vasella A. Tetrahedron Lett. 25 (1984) 5381
18. Bull J.R., Jones E.R.H., and Meakins G.D. J. Chem. Soc. (1965) 2601
19. Iffland D.C., and Fu-Yen T. J. Am. Chem. Soc. 76 (1954) 4083
20. Wichterle O., and Hudlicky M. Collect. Czech. Chem. Commun. 12 (1947) 661
21. Cuthbertson F., and Musgrave W.K.R. J. Appl. Chem. 7 (1957) 99
22. Doering W.Von., and Henderson Jr. W.A. J. Am. Chem. Soc. 80 (1958) 5274
23. Orazi O.O., Corral R.A., and Schuttenberg H. J. Chem. Soc., Perkin Trans. 1 (1974) 2087
24. Olah G.A., and Welch J. Synthesis (1974) 2087
25. Seyferth D., Murphy G.J., and Mauze B. J. Am. Chem. Soc. 99 (1977) 5317
26. Villieras J., Perriot P., and Normant J.F. Bull. Soc. Chim. Fr. (1977) 765
27. Kruglova N.V., and Freidline R.K. Bull. Acad. Sci. USSR, Engl. Trans. (1984) 346
28. Lee G.M., and Weinreb S.M. J. Org. Chem. 55 (1990) 1281
29. Migrdiechian V. Organic Synthesis. Open Chain Saturated Compounds Vol. 1 (1960), Chapman and Hall, London p 702
30. Laszlo P. Organic Reactions: Simplicity and Logic (1995), Wiley, New York
31. Dubey D.K., Malhotra R.C., Vaidyanathaswamy R., and Vijayraghavan R. J. Org. Chem. 64 (1993) 8301
32. Vijayraghavan R., Praveen Kumar, Dubey D.K., and Ram Singh. Biomed. Enviro. Sci. 15 (2002) 25
33. Shakya P.D., Dubey D.K., Pardasani D., Palit M., and Gupta A.K. J. Chem. Res. (2005) 821-823
34. -1.
35. Preparation of N,N′-dichloro bis(2,4,6-trichlorophenyl)urea (CC-2): Bis(diphenyl)urea (25 g, 0.117 mol) was dissolved in 200 mL of acetic acid and 20 mL of pyridine was added followed by stirring at 70 °C. Chlorine gas was bubbled into the reaction for 4 h with stirring. Absorption of chlorine ceased with complete precipitation of bis(2,4,6-trichlorophenyl)urea. The mixture was cooled to 10 °C in an ice bath, and solid NaOH (7 g) was added in portions to bring the pH of the mixture to almost neutral. Chlorine gas was passed through until all the organic matter had re-dissolved. The mixture was poured into water to precipitate the CC-2, which was washed with water, filtered and re-crystallized from toluene. After drying, the yield was 56 g, 98%, mp 179-180 °C. The chlorine content of CC-2 was checked by standard iodometric titration and was found to be 14.51% (theoretical value 14.54%).