GB620800A - Improvements in or relating to organic compounds - Google Patents
Improvements in or relating to organic compoundsInfo
- Publication number
- GB620800A GB620800A GB223747A GB223747A GB620800A GB 620800 A GB620800 A GB 620800A GB 223747 A GB223747 A GB 223747A GB 223747 A GB223747 A GB 223747A GB 620800 A GB620800 A GB 620800A
- Authority
- GB
- United Kingdom
- Prior art keywords
- dicyanoketene
- refluxing
- methyl
- diethylmercaptole
- triethylamine
- 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
- 150000002894 organic compounds Chemical class 0.000 title 1
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 abstract 18
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 12
- 238000010992 reflux Methods 0.000 abstract 7
- 235000019441 ethanol Nutrition 0.000 abstract 6
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 abstract 4
- VUQUOGPMUUJORT-UHFFFAOYSA-N methyl 4-methylbenzenesulfonate Chemical compound COS(=O)(=O)C1=CC=C(C)C=C1 VUQUOGPMUUJORT-UHFFFAOYSA-N 0.000 abstract 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 abstract 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 3
- MUDSDYNRBDKLGK-UHFFFAOYSA-N 4-methylquinoline Chemical compound C1=CC=C2C(C)=CC=NC2=C1 MUDSDYNRBDKLGK-UHFFFAOYSA-N 0.000 abstract 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 abstract 2
- 239000000975 dye Substances 0.000 abstract 2
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 abstract 2
- VCJMYUPGQJHHFU-UHFFFAOYSA-N iron(3+);trinitrate Chemical compound [Fe+3].[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O VCJMYUPGQJHHFU-UHFFFAOYSA-N 0.000 abstract 2
- DXYYSGDWQCSKKO-UHFFFAOYSA-N methylbenzothiazole Natural products C1=CC=C2SC(C)=NC2=C1 DXYYSGDWQCSKKO-UHFFFAOYSA-N 0.000 abstract 2
- JUIQOABNSLTJSW-UHFFFAOYSA-N 2-Methyl-4,5-dihydro-1,3-thiazole Chemical compound CC1=NCCS1 JUIQOABNSLTJSW-UHFFFAOYSA-N 0.000 abstract 1
- CVULGJIRGZVJHQ-UHFFFAOYSA-N 2-ethylbenzothiazole Chemical compound C1=CC=C2SC(CC)=NC2=C1 CVULGJIRGZVJHQ-UHFFFAOYSA-N 0.000 abstract 1
- DQSHFKPKFISSNM-UHFFFAOYSA-N 2-methylbenzoxazole Chemical compound C1=CC=C2OC(C)=NC2=C1 DQSHFKPKFISSNM-UHFFFAOYSA-N 0.000 abstract 1
- SJLJHVITDDTVMW-UHFFFAOYSA-N C[S+]1C2=CC=CC=C2N=C1 Chemical compound C[S+]1C2=CC=CC=C2N=C1 SJLJHVITDDTVMW-UHFFFAOYSA-N 0.000 abstract 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 abstract 1
- YDQJXVYGARVLRT-UHFFFAOYSA-N Lepidine Natural products C=1C=CC(CC=2NC=CN=2)=CC=1OC=1C(OC)=CC=CC=1CC1=NC=CN1 YDQJXVYGARVLRT-UHFFFAOYSA-N 0.000 abstract 1
- 229910052783 alkali metal Inorganic materials 0.000 abstract 1
- 150000001340 alkali metals Chemical class 0.000 abstract 1
- 230000002152 alkylating effect Effects 0.000 abstract 1
- 229910021529 ammonia Inorganic materials 0.000 abstract 1
- 230000008020 evaporation Effects 0.000 abstract 1
- 238000001704 evaporation Methods 0.000 abstract 1
- -1 heterocyclic nitrogen compound Chemical class 0.000 abstract 1
- 125000001434 methanylylidene group Chemical group [H]C#[*] 0.000 abstract 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 1
- 229910017464 nitrogen compound Inorganic materials 0.000 abstract 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 abstract 1
- 150000003839 salts Chemical group 0.000 abstract 1
- 229910052708 sodium Inorganic materials 0.000 abstract 1
- 239000011734 sodium Substances 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/52—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings condensed with carbocyclic rings or ring systems
- C07D263/54—Benzoxazoles; Hydrogenated benzoxazoles
- C07D263/56—Benzoxazoles; Hydrogenated benzoxazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/12—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/08—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D277/10—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
- C07D277/62—Benzothiazoles
- C07D277/64—Benzothiazoles with only hydrocarbon or substituted hydrocarbon radicals attached in position 2
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
- C07D277/84—Naphthothiazoles
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03C—PHOTOSENSITIVE MATERIALS FOR PHOTOGRAPHIC PURPOSES; PHOTOGRAPHIC PROCESSES, e.g. CINE, X-RAY, COLOUR, STEREO-PHOTOGRAPHIC PROCESSES; AUXILIARY PROCESSES IN PHOTOGRAPHY
- G03C1/00—Photosensitive materials
- G03C1/005—Silver halide emulsions; Preparation thereof; Physical treatment thereof; Incorporation of additives therein
- G03C1/06—Silver halide emulsions; Preparation thereof; Physical treatment thereof; Incorporation of additives therein with non-macromolecular additives
- G03C1/08—Sensitivity-increasing substances
- G03C1/10—Organic substances
- G03C1/12—Methine and polymethine dyes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- General Physics & Mathematics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
b : b -Dicyanoketene dialkylmercaptoles are prepared by reacting carbon disulphide with a dry alkali-metal derivative of malodinitrile and alkylating the product. b : b -Dicyanoketene dimethylmercaptole is prepared by adding sodium to liquid ammonia in presence of ferric nitrate and then adding malodinitrile. After evaporation of the ammonia, diethyl ether is added and then carbon disulphide, and the resulting mixture is refluxed with methyl iodide. b : b -Dicyanoketene diethylmercaptole is similarly prepared.ALSO:Methine dyes are prepared by reacting a b : b -dicyanoketene dialkylmercaptol with a quaternary salt of a heterocyclic nitrogen compound containing a reactive methylene group in a or g -position to the quaternary N atom. Dyes are prepared by (a) fusing together b : b -dicyanoketene dimethylmercaptole, 1-methyl-benzthiazole and methyl p-toluenesulphonate, adding pyridine and refluxing, (b) refluxing together b : b -dicyanoketene diethylmercaptole, 2-methylbenzoxazole ethiodide, ethyl alcohol and triethylamine, (c) fusing together 2-methyl-b -naphthathiazole and methyl p-toluenesulphonate, adding b : b -dicyanoketene diethylmercaptole, ethyl alcohol and triethylamine, and refluxing, (d) refluxing together b : b -dicyanoketene dimethylmercaptole, lepidine methiodide, ethyl alcohol and triethylamine, (e) fusing together b : b -dicyanoketene diethylmercaptole, 2-methylthiazoline and methyl p-toluenesulphonate, adding ethyl alcohol and triethylamine, and refluxing, (f) refluxing together b : b -dicyanoketene diethylmercaptole, 2-methylbenzthiazole ethiodide, ethyl alcohol and triethylamine, and (g) fusing together b : b -dicyanoketene diethylmercaptole, 2-ethylbenzthiazole and methyl p-toluenesulphonate, adding ethyl alcohol and triethylamine, and refluxing.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB223747A GB620800A (en) | 1947-01-24 | 1947-01-24 | Improvements in or relating to organic compounds |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB223747A GB620800A (en) | 1947-01-24 | 1947-01-24 | Improvements in or relating to organic compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB620800A true GB620800A (en) | 1949-03-30 |
Family
ID=9736015
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB223747A Expired GB620800A (en) | 1947-01-24 | 1947-01-24 | Improvements in or relating to organic compounds |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB620800A (en) |
-
1947
- 1947-01-24 GB GB223747A patent/GB620800A/en not_active Expired
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| GB926691A (en) | Improvements in sensitized photographic emulsions and in sensitizing dyes therefor | |
| GB868798A (en) | Improvements in photographic sensitizing dyes | |
| GB620800A (en) | Improvements in or relating to organic compounds | |
| GB620482A (en) | Trinuclear cyanine dyes and photographic light-sensitive elements containing them | |
| GB654690A (en) | Improvements in cyanine dyes and photographic emulsions containing the same | |
| GB807460A (en) | Merocyanine dyes and photographic silver halide emulsions containing them | |
| GB646896A (en) | An improved process of preparing trinuclear cyanine dyes | |
| GB684386A (en) | Process for preparing methine dyes | |
| GB694744A (en) | Improvements in or relating to dyestuffs and photographic emulsions containing the same | |
| GB776414A (en) | Merocyanine dyes, methods of making them and photographic emulsions containing them | |
| GB684707A (en) | Improvements in or relating to the production of dyestuffs and to the sensitising of photographic emulsions therewith | |
| GB678626A (en) | Improvements in or relating to carbocyanine dyes | |
| GB620802A (en) | Improvements in or relating to dyestuffs | |
| GB786168A (en) | Photographic emulsions | |
| GB693624A (en) | Improvements in or relating to dyestuffs | |
| GB871113A (en) | Cyanine bases and undissociated cyanine dyes containing an azaindenyl nucleus | |
| GB675227A (en) | Improvements in or relating to cyanine dyes | |
| GB850482A (en) | Improvements in or relating to photographic desensitised emulsions | |
| GB629123A (en) | Improvements in the manufacture of intermediates for the production of dyes, in the manufacture of polymethin dyes and in photographic silver salt emulsions containing such dyes | |
| GB595784A (en) | Improvements in or relating to cyanine dyestuffs | |
| GB721203A (en) | Process for sensitizing and supersensitizing photographic emulsions | |
| GB628837A (en) | Improvements in and relating to the preparation of dyestuff intermediates and of dyestuffs therefrom | |
| GB638047A (en) | Improvements in or relating to merocyanine dyestuffs | |
| GB616223A (en) | Manufacture of dyestuffs | |
| GB646900A (en) | Thiazolone cyanine dyes and the method of preparing the same |