US2000578A - Pyridinium iodides and process of preparing them - Google Patents
Pyridinium iodides and process of preparing them Download PDFInfo
- Publication number
- US2000578A US2000578A US697067A US69706733A US2000578A US 2000578 A US2000578 A US 2000578A US 697067 A US697067 A US 697067A US 69706733 A US69706733 A US 69706733A US 2000578 A US2000578 A US 2000578A
- Authority
- US
- United States
- Prior art keywords
- alkyl
- preparing
- iodide
- pyridinium
- iodides
- 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 - Lifetime
Links
- 238000000034 method Methods 0.000 title description 7
- BJDYCCHRZIFCGN-UHFFFAOYSA-N pyridin-1-ium;iodide Chemical class I.C1=CC=NC=C1 BJDYCCHRZIFCGN-UHFFFAOYSA-N 0.000 title 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 10
- -1 2-quinolyl alkyl iodide Chemical class 0.000 description 7
- 150000001875 compounds Chemical class 0.000 description 6
- 239000000543 intermediate Substances 0.000 description 5
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 5
- 125000000217 alkyl group Chemical group 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 241000209149 Zea Species 0.000 description 2
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 2
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 2
- 150000001351 alkyl iodides Chemical class 0.000 description 2
- 235000005822 corn Nutrition 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- QGKMIGUHVLGJBR-UHFFFAOYSA-M (4z)-1-(3-methylbutyl)-4-[[1-(3-methylbutyl)quinolin-1-ium-4-yl]methylidene]quinoline;iodide Chemical compound [I-].C12=CC=CC=C2N(CCC(C)C)C=CC1=CC1=CC=[N+](CCC(C)C)C2=CC=CC=C12 QGKMIGUHVLGJBR-UHFFFAOYSA-M 0.000 description 1
- FECNOIODIVNEKI-UHFFFAOYSA-N 2-[(2-aminobenzoyl)amino]benzoic acid Chemical class NC1=CC=CC=C1C(=O)NC1=CC=CC=C1C(O)=O FECNOIODIVNEKI-UHFFFAOYSA-N 0.000 description 1
- XVMSFILGAMDHEY-UHFFFAOYSA-N 6-(4-aminophenyl)sulfonylpyridin-3-amine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=N1 XVMSFILGAMDHEY-UHFFFAOYSA-N 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 125000005678 ethenylene group Chemical group [H]C([*:1])=C([H])[*:2] 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 150000004694 iodide salts Chemical class 0.000 description 1
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- JUJWROOIHBZHMG-UHFFFAOYSA-O pyridinium Chemical compound C1=CC=[NH+]C=C1 JUJWROOIHBZHMG-UHFFFAOYSA-O 0.000 description 1
- 150000003839 salts Chemical group 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/06—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom
- C07D213/22—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom containing two or more pyridine rings directly linked together, e.g. bipyridyl
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
Definitions
- This invention relates to intermediates used in the preparation of cyanine dyes of the tricarbocyanine series. These intermediates may be termed (2-quinolyl alkyl iodide) -pyridinium 5 iodides and (Z-pyridyl alkyl iodidel-pyridinium iodides.
- This application is a division of my copending application Serial No. 652,030 filed January 16, 1933.
- the method of preparing these intermediates is as follows: Equimolecular proportions of 2-iodoquinoline alkyl iodides and pyridine are caused to combine to give intermediate compounds of a new type, probably represented by the following formula-- N R/N ⁇ I (Z-quinolyl alkyl iodide)-pyridinium iodide These intermediate compounds can be isolated by treating the finely pulverized 2-iodoquino1ine alkyl iodides with pyridine, preferably in the cold, for 12 to 24 hours, and are then obtained as orange colored solids which can be purified by very rapid recrystallization from water. It is convenient to employ a large excess of pyridine in the reaction.
- the new compounds are unstable towards recrystallization butare quite soluble in hot water, whereas the 2-iodoquinoline alkyl iodides are only sparingly soluble.
- (2- quinolyl methiodide)-pyridinium iodide is obtained as orange-ochre crystals on recrystallization from water and melts at I'm-171 C. (with decomp.) (corn)- The corresponding ethiodide melts at 167-168 (with decomp.) (corn).
- methyl and ethyl groups are the alkyl radicals which I commonly employ in the alkyl iodides used as startingmaterials, it is obvious that I may employ any of the other alkyl radicals commonly known to those skilled in the art.
- R represents an alkyl group and B represents a substituent selected from the group consisting of vinylene and phenylene.
Description
Patented May 7, 1935 PATENT OFFICE PYRIDINIUM IODIDESAND PROCESS OF 1 PREPARING THEM Leslie G. S. Brooker, Rochester, N. Y., assignor to Eastman Kodak Company, Rochester, N. Y., a corporation of New York No Drawing. Original application January 16,
1933, Serial No. 652,030. Divided and this application November 7, 1933, Serial No. 697,067
6 Claims.
This invention relates to intermediates used in the preparation of cyanine dyes of the tricarbocyanine series. These intermediates may be termed (2-quinolyl alkyl iodide) -pyridinium 5 iodides and (Z-pyridyl alkyl iodidel-pyridinium iodides. This application is a division of my copending application Serial No. 652,030 filed January 16, 1933.
It is an object of my invention, therefore, to
provide these new dye intermediates and a method of preparing them.
In general, the method of preparing these intermediates is as follows: Equimolecular proportions of 2-iodoquinoline alkyl iodides and pyridine are caused to combine to give intermediate compounds of a new type, probably represented by the following formula-- N R/N\I (Z-quinolyl alkyl iodide)-pyridinium iodide These intermediate compounds can be isolated by treating the finely pulverized 2-iodoquino1ine alkyl iodides with pyridine, preferably in the cold, for 12 to 24 hours, and are then obtained as orange colored solids which can be purified by very rapid recrystallization from water. It is convenient to employ a large excess of pyridine in the reaction. The new compounds are unstable towards recrystallization butare quite soluble in hot water, whereas the 2-iodoquinoline alkyl iodides are only sparingly soluble. (2- quinolyl methiodide)-pyridinium iodide is obtained as orange-ochre crystals on recrystallization from water and melts at I'm-171 C. (with decomp.) (corn)- The corresponding ethiodide melts at 167-168 (with decomp.) (corn).
The Z-iodopyridine alkyl iodides, in a similar fashion, give rise to the compounds probably possessing the structural formula R=alkyl (2-pyrldy1 alkyl mamo-pyr dmmm iodide These compounds are yellow solids and are recrystallized in the same manner as described in the previous paragraph.
While the methyl and ethyl groups are the alkyl radicals which I commonly employ in the alkyl iodides used as startingmaterials, it is obvious that I may employ any of the other alkyl radicals commonly known to those skilled in the art.
What I claim as my invention and. desire to be secured by Letters Patent of the United States is: g
1. (Z-quinolyl alkyl iodide) -pyridinium iodide.
2. (2-pyridyl alkyl iodide) -pyridinium iodide.
3. The process which comprises-condensing pyridine with a compound of the following structure:
wherein R represents an alkyl group and B represents a substituent selected from the group consisting of vinylene and phenylene.
4. The process which comprises condensing pyridine with a 2-iodopyridine alkyl iodide.
5. The process which comprises condensing pyridine with a 2-iodoquinoline alkyl iodide.
6. A quaternary salt of the following structure:
l R- A LESLIE G. s. BROOKER.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US697067A US2000578A (en) | 1933-01-16 | 1933-11-07 | Pyridinium iodides and process of preparing them |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US652030A US2094580A (en) | 1933-01-16 | 1933-01-16 | Tricarbocyanines and process of preparing them |
| US697067A US2000578A (en) | 1933-01-16 | 1933-11-07 | Pyridinium iodides and process of preparing them |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2000578A true US2000578A (en) | 1935-05-07 |
Family
ID=27096214
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US697067A Expired - Lifetime US2000578A (en) | 1933-01-16 | 1933-11-07 | Pyridinium iodides and process of preparing them |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US2000578A (en) |
-
1933
- 1933-11-07 US US697067A patent/US2000578A/en not_active Expired - Lifetime
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