GB785939A - Improvements in or relating to the production of thiadiazole derivatives - Google Patents
Improvements in or relating to the production of thiadiazole derivativesInfo
- Publication number
- GB785939A GB785939A GB469555A GB469555A GB785939A GB 785939 A GB785939 A GB 785939A GB 469555 A GB469555 A GB 469555A GB 469555 A GB469555 A GB 469555A GB 785939 A GB785939 A GB 785939A
- Authority
- GB
- United Kingdom
- Prior art keywords
- formula
- group
- methyl
- alkyl
- prepared
- 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
- 150000004867 thiadiazoles Chemical class 0.000 title abstract 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 abstract 12
- 125000000217 alkyl group Chemical group 0.000 abstract 11
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 6
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 4
- 150000001875 compounds Chemical class 0.000 abstract 4
- 238000010438 heat treatment Methods 0.000 abstract 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 abstract 3
- 125000003118 aryl group Chemical group 0.000 abstract 3
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 abstract 2
- 150000001450 anions Chemical group 0.000 abstract 2
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 abstract 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 abstract 2
- 239000000975 dye Substances 0.000 abstract 2
- 150000002148 esters Chemical class 0.000 abstract 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 2
- -1 heterocyclic nitrogen keto methylene compound Chemical class 0.000 abstract 2
- 229910052739 hydrogen Inorganic materials 0.000 abstract 2
- 239000001257 hydrogen Substances 0.000 abstract 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 2
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine group Chemical group N1=CCC2=CC=CC=C12 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 abstract 2
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 abstract 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 abstract 2
- 125000001434 methanylylidene group Chemical group [H]C#[*] 0.000 abstract 2
- 229910052757 nitrogen Inorganic materials 0.000 abstract 2
- SJHPCNCNNSSLPL-CSKARUKUSA-N (4e)-4-(ethoxymethylidene)-2-phenyl-1,3-oxazol-5-one Chemical compound O1C(=O)C(=C/OCC)\N=C1C1=CC=CC=C1 SJHPCNCNNSSLPL-CSKARUKUSA-N 0.000 abstract 1
- BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical compound C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 abstract 1
- SLYRGJDSFOCAAI-UHFFFAOYSA-N 1,3-thiazolidin-2-one Chemical compound O=C1NCCS1 SLYRGJDSFOCAAI-UHFFFAOYSA-N 0.000 abstract 1
- RSEBUVRVKCANEP-UHFFFAOYSA-N 2-pyrroline Chemical compound C1CC=CN1 RSEBUVRVKCANEP-UHFFFAOYSA-N 0.000 abstract 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 125000002252 acyl group Chemical group 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 150000008064 anhydrides Chemical class 0.000 abstract 1
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 abstract 1
- 229940073608 benzyl chloride Drugs 0.000 abstract 1
- 125000002837 carbocyclic group Chemical group 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- 238000001816 cooling Methods 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 125000000623 heterocyclic group Chemical group 0.000 abstract 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 abstract 1
- 229910052500 inorganic mineral Inorganic materials 0.000 abstract 1
- HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 abstract 1
- 239000011707 mineral Substances 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
- WYVAMUWZEOHJOQ-UHFFFAOYSA-N propionic anhydride Chemical compound CCC(=O)OC(=O)CC WYVAMUWZEOHJOQ-UHFFFAOYSA-N 0.000 abstract 1
- JEXVQSWXXUJEMA-UHFFFAOYSA-N pyrazol-3-one Chemical compound O=C1C=CN=N1 JEXVQSWXXUJEMA-UHFFFAOYSA-N 0.000 abstract 1
- ZVJHJDDKYZXRJI-UHFFFAOYSA-N pyrroline Natural products C1CC=NC1 ZVJHJDDKYZXRJI-UHFFFAOYSA-N 0.000 abstract 1
- KIWUVOGUEXMXSV-UHFFFAOYSA-N rhodanine Chemical compound O=C1CSC(=S)N1 KIWUVOGUEXMXSV-UHFFFAOYSA-N 0.000 abstract 1
- 150000003839 salts Chemical group 0.000 abstract 1
- 125000001424 substituent group Chemical group 0.000 abstract 1
- 239000001117 sulphuric acid Substances 0.000 abstract 1
- 235000011149 sulphuric acid Nutrition 0.000 abstract 1
- 125000002769 thiazolinyl group Chemical group 0.000 abstract 1
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
- C09B23/10—The polymethine chain containing an even number of >CH- groups
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
Methine dyes are prepared by condensing a compound of formula <FORM:0785939/IV (b)/1> wherein R1 is hydrogen or an alkyl group, R2 is a lower alkyl group or an aralkyl group, R3 is an alkyl group and X is an anion, with a compound of the formula <FORM:0785939/IV (b)/2> wherein R4 is an alkyl, aralkyl or hydroxyalkyl group, n is 0 or 1, Y is an anion, D1 completes a heterocyclic nucleus and Q is -SR or -CH=CH-SR (R=alkyl or aralkyl) or an acetanilidovinyl group, or with a compound of the formula <FORM:0785939/IV (b)/3> wherein D2 completes a heterocyclic nitrogenous ring and R5 is an alkyl group. The reactions occur at the R1-CH2- group to give dyes having a substituted mercapto-thio-b b -diazole nucleus and an R1 substituent in the methine chain. The compound of the last formula may be replaced by the heterocyclic nitrogen keto methylene compound and an excess of an alkyl orthoformate CH(OR5)3. D1 may complete a benzthiazole, benzoxazole, quinoline, indolenine, pyrroline or thiazoline ring and the carbocyclic rings may contain halogen, alkyl, alkoxy or aryl substituents. D2 may complete a rhodanine, pyrazolone, oxazolone, thiazolidone or benziminazo-thiazolidone nucleus. According to the Provisional Specification, R2 may be aryl. Specifications 425,609, [Group IV], 730,489 and 743,133 are referred to.ALSO:Thiadiazoles of the general formula: <FORM:0785939/IV (a)/1> wherein R1 is hydrogen or an alkyl group and R2 is an alkyl group of 1 to 4 carbon atoms or an aralkyl group, are prepared by heating an acyl dithiocarbazinic ester of the formula: <FORM:0785939/IV (a)/2> with a mineral acid or an aliphatic mono-carboxylic acid anhydride. Alternatively a dithiocarbazinic ester of the formula: NH2-NH-C:S-SR2 may be heated with excess anhydride of the formula (R1CH2CO)2O. The thiadiazoles may be quaternized on nitrogen atom 3 by heating with an alkyl salt. Examples are given of heating methyl 2-acetyldithiocarbazinate with acetic anhydride or sulphuric acid, and of heating methyl dithiocarbazinate with excess acetic anhydride to give 2-methyl-5-methylthio-1:3:4-thiadiazole. Similarly, benzyl, isopropyl and ethyl dithiocarbazinates are heated with excess acetic anhydride and methyl dithiocarbazinate is heated with excess propionic anhydride. Examples are given of treating the thiadiazoles produced as above with methyl iodide or ethyl iodide to give the quaternary salts. According to the Provisional Specification, R2 in the above formula may be aryl. Methyl and benzyl dithiocarbazinates are prepared from NH2.NHCS2K and methyl iodide or benzyl chloride respectively. The ethyl and isopropyl esters are similarly prepared. Methyl acetyldithiocarbazinate is prepared by adding acetic anhydride to methyl dithiocarbazinate in acetic acid while cooling to keep the temperature at 15-20 DEG C. Specifications 425,609, [Group IV], 730,489 and 743,133 are referred to.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB469555A GB785939A (en) | 1955-02-16 | 1955-02-16 | Improvements in or relating to the production of thiadiazole derivatives |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB469555A GB785939A (en) | 1955-02-16 | 1955-02-16 | Improvements in or relating to the production of thiadiazole derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB785939A true GB785939A (en) | 1957-11-06 |
Family
ID=9782057
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB469555A Expired GB785939A (en) | 1955-02-16 | 1955-02-16 | Improvements in or relating to the production of thiadiazole derivatives |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB785939A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2002080159A1 (en) * | 2001-03-28 | 2002-10-10 | Bayer Aktiengesellschaft | Optical data carrier that contains a cyanine dye as the light-absorbing compound in the information layer |
-
1955
- 1955-02-16 GB GB469555A patent/GB785939A/en not_active Expired
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2002080159A1 (en) * | 2001-03-28 | 2002-10-10 | Bayer Aktiengesellschaft | Optical data carrier that contains a cyanine dye as the light-absorbing compound in the information layer |
| US6835725B2 (en) | 2001-03-28 | 2004-12-28 | Bayer Aktiengesellschaft | Optical data carrier comprising a cyanine dye as light-absorbent compound in the information layer |
| US7041354B2 (en) | 2001-03-28 | 2006-05-09 | Bayer Aktiengesellschaft | Optical data carrier comprising a cyanine dye as light-absorbent compound in the information layer |
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