GB595785A - Improvements in or relating to dyestuff intermediates - Google Patents
Improvements in or relating to dyestuff intermediatesInfo
- Publication number
- GB595785A GB595785A GB1976246A GB1976246A GB595785A GB 595785 A GB595785 A GB 595785A GB 1976246 A GB1976246 A GB 1976246A GB 1976246 A GB1976246 A GB 1976246A GB 595785 A GB595785 A GB 595785A
- Authority
- GB
- United Kingdom
- Prior art keywords
- ethylthio
- cyclohexenone
- toluenesulphonate
- methyl
- acetic anhydride
- 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
- 239000000543 intermediate Substances 0.000 title abstract 3
- 239000000975 dye Substances 0.000 title 1
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 abstract 18
- VRZVPALEJCLXPR-UHFFFAOYSA-N ethyl 4-methylbenzenesulfonate Chemical compound CCOS(=O)(=O)C1=CC=C(C)C=C1 VRZVPALEJCLXPR-UHFFFAOYSA-N 0.000 abstract 4
- 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 3
- 238000009835 boiling Methods 0.000 abstract 3
- 150000001875 compounds Chemical class 0.000 abstract 3
- VUQUOGPMUUJORT-UHFFFAOYSA-N methyl 4-methylbenzenesulfonate Chemical compound COS(=O)(=O)C1=CC=C(C)C=C1 VUQUOGPMUUJORT-UHFFFAOYSA-N 0.000 abstract 3
- -1 6-membered heterocyclic nitrogen compound Chemical class 0.000 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 2
- 150000007514 bases Chemical class 0.000 abstract 2
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 abstract 2
- 229910052757 nitrogen Inorganic materials 0.000 abstract 2
- SMUQFGGVLNAIOZ-UHFFFAOYSA-N quinaldine Chemical compound C1=CC=CC2=NC(C)=CC=C21 SMUQFGGVLNAIOZ-UHFFFAOYSA-N 0.000 abstract 2
- 238000010992 reflux Methods 0.000 abstract 2
- JJPSZKIOGBRMHK-UHFFFAOYSA-N 2,6-dimethylquinoline Chemical compound N1=C(C)C=CC2=CC(C)=CC=C21 JJPSZKIOGBRMHK-UHFFFAOYSA-N 0.000 abstract 1
- JKLZCQWVERBDEZ-UHFFFAOYSA-N 3-methyl-2-sulfanylidene-1,3-thiazolidin-4-one Chemical compound CN1C(=O)CSC1=S JKLZCQWVERBDEZ-UHFFFAOYSA-N 0.000 abstract 1
- LARAXTIHRJWABJ-UHFFFAOYSA-N 4-(2-phenylethenyl)cyclohexane-1,2-dione Chemical compound C(=CC1=CC=CC=C1)C1CCC(C(C1)=O)=O LARAXTIHRJWABJ-UHFFFAOYSA-N 0.000 abstract 1
- RUSILPVRZDMUDT-UHFFFAOYSA-N 4-propan-2-ylcyclohexane-1,2-dione Chemical compound CC(C)C1CCC(=O)C(=O)C1 RUSILPVRZDMUDT-UHFFFAOYSA-N 0.000 abstract 1
- 125000002373 5 membered heterocyclic group Chemical group 0.000 abstract 1
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 abstract 1
- QELUYTUMUWHWMC-UHFFFAOYSA-N edaravone Chemical compound O=C1CC(C)=NN1C1=CC=CC=C1 QELUYTUMUWHWMC-UHFFFAOYSA-N 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract 1
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 1
- 229910017464 nitrogen compound Inorganic materials 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 abstract 1
- 150000003839 salts Chemical group 0.000 abstract 1
Classifications
-
- 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
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
-
- 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
- C07D215/14—Radicals substituted by oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D231/18—One oxygen or sulfur atom
- C07D231/20—One oxygen atom attached in position 3 or 5
- C07D231/22—One oxygen atom attached in position 3 or 5 with aryl radicals attached to ring nitrogen atoms
- C07D231/26—1-Phenyl-3-methyl-5- pyrazolones, unsubstituted or substituted on the phenyl ring
-
- 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
Abstract
A dye intermediate is prepared by heating a compound of the forumula of Fig. 1. <PICT:0595785/IV/1> wherein R is an alkyl or aralkyl group and D a chain of 3 methylene groups, any of which may be hydrocarbon-substituted with an alkyl or aralkyl quaternary salt of a 5- or 6-membered heterocyclic nitrogen compound containing a reactive methylene group in a - or g -position to the quarternary nitrogen atom or a 5-membered heterocyclic nitrogen keto-methylene compound, the reaction being effected in presence of a non-basic compound which will combine with the liberated mercaptan RSH. The first compound may be D 2 : 3 - (3 - ethylthio - 5 : 5 - dimethyl)-cyclohexenone (1), D 2 : 3 - (3-ethylthio - 5 - phenyl) - cyclohexenone (1), D 2 : 3 - (3 - ethylthio - 5 - methyl) - cyclohexenone (1), or D 2 : 3 - (3 - ethylthio) - cyclohexenone (1), or an analogous compound prepared as in Specification 595,783 from 5-isopropylcyclohexanedione (1 : 3), 4 : 5 : 5-trimethylcyclohexanedione (1 : 3), 4 - phenyl - 5 : 5 - dimethylcyclohexanonedione (1 : 3), or 5-styrylcyclohexanedione (1 : 3). The non-basic compound may be acetic anhydride. Examples are given of the preparation of intermediates (1) by fusing together D 2 : 3-(3-ethylthio - 5 : 5 - dimethyl) - cyclohexenone (1), 1 - methylbenzthiazole, and methyl p-toluenesulphonate, adding acetic anhydride, refluxing and pouring into aqueous KI solution; (2) to (4) by proceeding similarly to example (1), but obtaining the methyl-p-toluenesulphonate, the ethiodide, and the ethyl-p-toluenesulphonate respectively; (5) by proceeding similarly to example (1), but using ethyl-p-toluenesulphonate and quinaldine; (6) by proceeding similarly to example (1), but using ethyl-p-toluenesulphonate and p-toluquinaldine; (7) by fusing together 1-methylbenzthiazole and ethyl p-toluenesulphonate, adding D 2 : 3-(3-ethylthio-5-methyl) - cyclohexenone (1), refusing, adding acetic anhydride, and refluxing; (8) by fusing together 1 - methylbenzthiazole, methyl p-toluenesulphonate, D 2 : 3 - (3-ethylthio)-cyclo - hexenone (1), adding acetic anhydride, and boiling; (9) by fusing together N-methylrhodanine and D 2 : 3 - (3 - ethylthio - 5 : 5 - dimethyl)-cyclohexenone (1), adding acetic anhydride and boiling; and (10) by fusing together 1-phenyl-3-methyl-5-pyrazolone and D 2 : 3-(3-ethylthio - 5 : 5 - dimethyl) - cyclohexenone (1), adding acetic anhydride, and boiling. Specification 595,784 also is referred to.
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB595785A true GB595785A (en) | 1947-12-16 |
Family
ID=1734969
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB1976246A Expired GB595785A (en) | 1945-07-03 | Improvements in or relating to dyestuff intermediates |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB595785A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2734900A (en) * | 1953-12-28 | 1956-02-14 | Chxgh | |
| US2856404A (en) * | 1956-06-20 | 1958-10-14 | Eastman Kodak Co | Merocyanine dyes and intermediates |
| US2887479A (en) * | 1955-11-15 | 1959-05-19 | Eastman Kodak Co | Heterocyclic quaternary salts containing a cyclohexenylidenemethyl substituent |
-
1945
- 1945-07-03 GB GB1976246A patent/GB595785A/en not_active Expired
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2734900A (en) * | 1953-12-28 | 1956-02-14 | Chxgh | |
| US2887479A (en) * | 1955-11-15 | 1959-05-19 | Eastman Kodak Co | Heterocyclic quaternary salts containing a cyclohexenylidenemethyl substituent |
| US2856404A (en) * | 1956-06-20 | 1958-10-14 | Eastman Kodak Co | Merocyanine dyes and intermediates |
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