GB618889A - Improvements in the manufacture of n:n-alkylenebenzimidazocyanine dyes - Google Patents
Improvements in the manufacture of n:n-alkylenebenzimidazocyanine dyesInfo
- Publication number
- GB618889A GB618889A GB2191546A GB2191546A GB618889A GB 618889 A GB618889 A GB 618889A GB 2191546 A GB2191546 A GB 2191546A GB 2191546 A GB2191546 A GB 2191546A GB 618889 A GB618889 A GB 618889A
- Authority
- GB
- United Kingdom
- Prior art keywords
- iodide
- prepared
- dyes
- product
- ethyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B23/00—Methine or polymethine dyes, e.g. cyanine dyes
- C09B23/02—Methine or polymethine dyes, e.g. cyanine dyes the polymethine chain containing an odd number of >CH- or >C[alkyl]- groups
- C09B23/04—Methine or polymethine dyes, e.g. cyanine dyes the polymethine chain containing an odd number of >CH- or >C[alkyl]- groups one >CH- group, e.g. cyanines, isocyanines, pseudocyanines
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
Di-1-ethyl-benzimidazolylmethane is prepared by refluxing together N-ethyl-o-phenylenediamine and ethyl malonate. Di-1-methyl-benzimidazolylmethane is similarly prepared. Specification 610,064 is referred to.ALSO:N : N1-Alkylenecyanine dyes of the general formula <FORM:0618889/IV (c)/1> wherein R is alkyl, Z is unsubstituted or substituted o-phenylene, X is an anion, and n is 2 or 3, are prepared by heating a di-2-(1-alkyl)-benzimidazolyl)-methane with an ethylene- or propylene-diarylsulphonate and treating the product with an acid binding agent. Dyes where n is 1 are prepared by heating a di-2-(1-alkyl)-benzimidazolylmethane with a methylene halide and treating the product with an acid-binding agent. The dyes may be converted to the corresponding iodides, bromides, or perchlorates. The acid-binding agent may be a trialkyl amine, a dialkylamine, an N-alkylpiperidine, sodium hydroxide or carbonate, or ammonia. 1 : 11 - Diethyl - 3 : 31 - ethylenebenzimidazolocyanine iodide is prepared by heating together di-1-ethylbenzimidazolylmethane and ethylene p-toluenesulphonate, adding sodium hydroxide to an ethyl alcohol solution of the product, and adding alcoholic sodium iodide to an ethyl alcohol solution of the dye p-toluenesulphonate obtained. 1 : 11 - Diethyl - 3 : 31 - trimethylene - benzimidazolocyanine iodide and 1 : 11-dimethyl-3 : 31 - ethylenebenzimidazolocyanine iodide are similarly prepared. 1 : 11 - Diethyl - 3 : 31 - methylenebenzimidazolocyanine iodide is prepared by heating together di - 1 - ethylbenzimidazolylmethane and methylene iodide and adding aqueous sodium hydroxide to a methyl alcohol solution of the product. 1 : 11 - Dimethyl - 3 : 31 - methylene - benzimidazolocyanine iodide is similarly prepared. Specificatio 610,064 is referred to.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB2191546A GB618889A (en) | 1946-07-23 | 1946-07-23 | Improvements in the manufacture of n:n-alkylenebenzimidazocyanine dyes |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB2191546A GB618889A (en) | 1946-07-23 | 1946-07-23 | Improvements in the manufacture of n:n-alkylenebenzimidazocyanine dyes |
Publications (1)
Publication Number | Publication Date |
---|---|
GB618889A true GB618889A (en) | 1949-03-01 |
Family
ID=10170934
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB2191546A Expired GB618889A (en) | 1946-07-23 | 1946-07-23 | Improvements in the manufacture of n:n-alkylenebenzimidazocyanine dyes |
Country Status (1)
Country | Link |
---|---|
GB (1) | GB618889A (en) |
Cited By (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3337579A (en) * | 1961-09-15 | 1967-08-22 | Upjohn Co | Unsymmetrical 2, 2'-alkylene-bisbenzimidazoles |
US3337578A (en) * | 1961-09-15 | 1967-08-22 | Heidenheimer Chemisches Lab | 2, 2'-alkylenebisbenzimidazoles |
GB2301832A (en) * | 1995-06-07 | 1996-12-18 | Univ Carnegie Mellon | Rigidized monomethine cyanine dyes by cyclisation of di(heterocyclyl)methane precursors |
US5852191A (en) * | 1995-06-07 | 1998-12-22 | Carnegie Mellon University | Rigidized monomethine cyanines |
US5981747A (en) * | 1995-06-07 | 1999-11-09 | Carnegie Mellon University | Monomethine cyanines rigidized by a two-carbon chain |
US8063032B2 (en) | 2009-02-11 | 2011-11-22 | Sunovion Pharmaceuticals Inc. | Histamine H3 inverse agonists and antagonists and methods of use thereof |
-
1946
- 1946-07-23 GB GB2191546A patent/GB618889A/en not_active Expired
Cited By (11)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3337579A (en) * | 1961-09-15 | 1967-08-22 | Upjohn Co | Unsymmetrical 2, 2'-alkylene-bisbenzimidazoles |
US3337578A (en) * | 1961-09-15 | 1967-08-22 | Heidenheimer Chemisches Lab | 2, 2'-alkylenebisbenzimidazoles |
GB2301832A (en) * | 1995-06-07 | 1996-12-18 | Univ Carnegie Mellon | Rigidized monomethine cyanine dyes by cyclisation of di(heterocyclyl)methane precursors |
GB2301832B (en) * | 1995-06-07 | 1998-03-11 | Univ Carnegie Mellon | Rigidized monomethine cyanine dyes |
US5852191A (en) * | 1995-06-07 | 1998-12-22 | Carnegie Mellon University | Rigidized monomethine cyanines |
US5981747A (en) * | 1995-06-07 | 1999-11-09 | Carnegie Mellon University | Monomethine cyanines rigidized by a two-carbon chain |
US5986093A (en) * | 1995-06-07 | 1999-11-16 | Carnegie Mellon University | Monomethine cyanines rigidized by a two-carbon chain |
US6207464B1 (en) | 1995-06-07 | 2001-03-27 | Carnegie Mellon University | Rigidized monomethine cyanines |
US6277984B1 (en) | 1995-06-07 | 2001-08-21 | Carnegie Mellon University | Monomethine cyanines rigidized by a two-carbon chain |
US8063032B2 (en) | 2009-02-11 | 2011-11-22 | Sunovion Pharmaceuticals Inc. | Histamine H3 inverse agonists and antagonists and methods of use thereof |
US8404670B2 (en) | 2009-02-11 | 2013-03-26 | Sunovion Pharmaceuticals Inc. | Histamine H3 inverse agonists and antagonists and methods of use thereof |
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