An improved procedure for the nitration of benzo-2,1,3-selenadiazoles and their reduction to ortho-phenylenediamines

Journal of Heterocyclic Chemistry

Volumn 41, Issue 6, 2004, Pages 1023-1026

  Wright, S W ^a   McClure, L D ^a  

^a PFIZER GLOBAL RESEARCH AND DEVELOPMENT   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

1,2 PHENYLENEDIAMINE; 3 NITRO 1,2 PHENYLENEDIAMINE; 4 FLUORO 3 NITROBENZENE 1,2 DIAMINE; BENZO 2,1,3 SELENADIAZOLE DERIVATIVE; FLUORIDE; HETEROCYCLIC COMPOUND; HYDRIODIC ACID; MESYLIC ACID; NITRIC ACID; NITROBENZENE DERIVATIVE; ORGANOSELENIUM DERIVATIVE; PHOSPHORUS PENTOXIDE; SODIUM NITRATE; SULFURIC ACID; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; GAS CHROMATOGRAPHY; MASS SPECTROMETRY; NITRATION; PROTON NUCLEAR MAGNETIC RESONANCE; REDUCTION; ROOM TEMPERATURE; SOLVOLYSIS; THIN LAYER CHROMATOGRAPHY;

EID: 12144273239     PISSN: 0022152X     EISSN: None     Source Type: Journal    
DOI: 10.1002/jhet.5570410629     Document Type: Article

References (8)

1. W. Tian, S. Grivas and K. Olsson, J. Chem. Soc., Perkin Trans. I, 257 (1993).
2. 13C NMR.
3. I. Achiwa, T. Shiozawa, H. Nukaya and Y. Terao, Chem. Pharm. Bull., 42, 408 (1994); S. Grivas, Acta Chem. Scand. B, 39, 213 (1985); M. S. Newman and E. H. Wiseman, J. Org. Chem., 26, 3208 (1961).
4. I. Achiwa, T. Shiozawa, H. Nukaya and Y. Terao, Chem. Pharm. Bull., 42, 408 (1994); S. Grivas, Acta Chem. Scand. B, 39, 213 (1985); M. S. Newman and E. H. Wiseman, J. Org. Chem., 26, 3208 (1961).
5. I. Achiwa, T. Shiozawa, H. Nukaya and Y. Terao, Chem. Pharm. Bull., 42, 408 (1994); S. Grivas, Acta Chem. Scand. B, 39, 213 (1985); M. S. Newman and E. H. Wiseman, J. Org. Chem., 26, 3208 (1961).
6. We wished to avoid heating the nitration mixture, as has been reported for the nitration of certain 2,1,3-selenadiazoles (see V. G. Pesin, V. A. Sergev and A. G. Nesterova, Chem. Heterocyclic Compounds, Eng. Trans., 75 (1966)) as we wished to avoid any possibility of initiating an uncontrollable exothermic decomposition of the nitration mixture.
7. E. Sawicki and A. Carr, J. Org. Chem., 22, 503 (1957).
8. It is important to ensure that the iodine is completely reduced prior to neutralization of the reaction mixture by ammonium hydroxide. If free iodine remains, it may react with ammonium hydroxide to precipitate the highly sensitive explosive nitrogen triiodide. Due to the intense violet - red color of the product 3, the color of the solution cannot be taken to indicate the absence of iodine.