GB410088A - Improvements in or relating to methods for the preparation of substituted thiazoles or selenazoles - Google Patents
Improvements in or relating to methods for the preparation of substituted thiazoles or selenazolesInfo
- Publication number
- GB410088A GB410088A GB3064732A GB3064732A GB410088A GB 410088 A GB410088 A GB 410088A GB 3064732 A GB3064732 A GB 3064732A GB 3064732 A GB3064732 A GB 3064732A GB 410088 A GB410088 A GB 410088A
- Authority
- GB
- United Kingdom
- Prior art keywords
- bromo
- methyl
- anhydride
- sodium
- product
- 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
- 150000003557 thiazoles Chemical class 0.000 title abstract 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 abstract 9
- -1 4-bromo-5-nitrocatechol methylene ether Chemical class 0.000 abstract 3
- 150000008064 anhydrides Chemical class 0.000 abstract 3
- 239000003513 alkali Substances 0.000 abstract 2
- XIMIGUBYDJDCKI-UHFFFAOYSA-N diselenium Chemical compound [Se]=[Se] XIMIGUBYDJDCKI-UHFFFAOYSA-N 0.000 abstract 2
- JVBXVOWTABLYPX-UHFFFAOYSA-L sodium dithionite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])=O JVBXVOWTABLYPX-UHFFFAOYSA-L 0.000 abstract 2
- GRVFOGOEDUUMBP-UHFFFAOYSA-N sodium sulfide (anhydrous) Chemical compound [Na+].[Na+].[S-2] GRVFOGOEDUUMBP-UHFFFAOYSA-N 0.000 abstract 2
- DGUDEQARXVYDBS-UHFFFAOYSA-N 1-bromo-4,5-dimethoxy-2-nitrobenzene Chemical compound COC1=CC(Br)=C([N+]([O-])=O)C=C1OC DGUDEQARXVYDBS-UHFFFAOYSA-N 0.000 abstract 1
- BFCFYVKQTRLZHA-UHFFFAOYSA-N 1-chloro-2-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1Cl BFCFYVKQTRLZHA-UHFFFAOYSA-N 0.000 abstract 1
- VRVRGVPWCUEOGV-UHFFFAOYSA-N 2-aminothiophenol Chemical class NC1=CC=CC=C1S VRVRGVPWCUEOGV-UHFFFAOYSA-N 0.000 abstract 1
- IQHSSYROJYPFDV-UHFFFAOYSA-N 2-bromo-1,3-dichloro-5-(trifluoromethyl)benzene Chemical group FC(F)(F)C1=CC(Cl)=C(Br)C(Cl)=C1 IQHSSYROJYPFDV-UHFFFAOYSA-N 0.000 abstract 1
- XMRDQEHOJBSXHN-UHFFFAOYSA-N 2-bromo-4-ethoxy-1-nitronaphthalene Chemical compound BrC=1C=C(C2=CC=CC=C2C1[N+](=O)[O-])OCC XMRDQEHOJBSXHN-UHFFFAOYSA-N 0.000 abstract 1
- RNEMUUFCMYMSQL-UHFFFAOYSA-N 3-bromo-1,2-dimethoxy-4-nitrobenzene Chemical compound COC1=CC=C([N+]([O-])=O)C(Br)=C1OC RNEMUUFCMYMSQL-UHFFFAOYSA-N 0.000 abstract 1
- GAILUAXTVXMGSC-UHFFFAOYSA-N 4-bromo-5-nitro-1,2-dihydroacenaphthylene Chemical compound BrC=1C=C2CCC=3C=CC=C(C1[N+](=O)[O-])C32 GAILUAXTVXMGSC-UHFFFAOYSA-N 0.000 abstract 1
- CSQUXTSIDQURDV-UHFFFAOYSA-N 6-bromo-1,3-benzodioxole-5-carbaldehyde Chemical compound C1=C(C=O)C(Br)=CC2=C1OCO2 CSQUXTSIDQURDV-UHFFFAOYSA-N 0.000 abstract 1
- XHJCHUVWJCDJPN-UHFFFAOYSA-N 9-bromo-10-nitrophenanthrene Chemical compound C1=CC=C2C([N+](=O)[O-])=C(Br)C3=CC=CC=C3C2=C1 XHJCHUVWJCDJPN-UHFFFAOYSA-N 0.000 abstract 1
- UWMJIAUUZGLXAN-UHFFFAOYSA-N CCN(CC)C1=CC=CC2=C1N=C[S+]2C Chemical compound CCN(CC)C1=CC=CC2=C1N=C[S+]2C UWMJIAUUZGLXAN-UHFFFAOYSA-N 0.000 abstract 1
- DNQJGZVBUKCQKN-UHFFFAOYSA-N CN(C)C1=CC=CC2=C1N=C[S+]2C Chemical compound CN(C)C1=CC=CC2=C1N=C[S+]2C DNQJGZVBUKCQKN-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
- BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical compound [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 abstract 1
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 abstract 1
- 150000001266 acyl halides Chemical class 0.000 abstract 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid group Chemical group C(C1=CC=CC=C1)(=O)O WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 abstract 1
- 239000000298 carbocyanine Substances 0.000 abstract 1
- 239000003153 chemical reaction reagent Substances 0.000 abstract 1
- GRWZHXKQBITJKP-UHFFFAOYSA-N dithionous acid Chemical compound OS(=O)S(O)=O GRWZHXKQBITJKP-UHFFFAOYSA-N 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- 238000004519 manufacturing process Methods 0.000 abstract 1
- 230000000802 nitrating effect Effects 0.000 abstract 1
- 150000007524 organic acids Chemical class 0.000 abstract 1
- 229920001021 polysulfide Polymers 0.000 abstract 1
- XMVJITFPVVRMHC-UHFFFAOYSA-N roxarsone Chemical group OC1=CC=C([As](O)(O)=O)C=C1[N+]([O-])=O XMVJITFPVVRMHC-UHFFFAOYSA-N 0.000 abstract 1
- 229910052711 selenium Inorganic materials 0.000 abstract 1
- 239000011669 selenium Substances 0.000 abstract 1
- VPQBLCVGUWPDHV-UHFFFAOYSA-N sodium selenide Chemical compound [Na+].[Na+].[Se-2] VPQBLCVGUWPDHV-UHFFFAOYSA-N 0.000 abstract 1
- 239000007858 starting material Substances 0.000 abstract 1
- 125000001424 substituent group Chemical group 0.000 abstract 1
- ANRHNWWPFJCPAZ-UHFFFAOYSA-M thionine Chemical compound [Cl-].C1=CC(N)=CC2=[S+]C3=CC(N)=CC=C3N=C21 ANRHNWWPFJCPAZ-UHFFFAOYSA-M 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D293/00—Heterocyclic compounds containing rings having nitrogen and selenium or nitrogen and tellurium, with or without oxygen or sulfur atoms, as the ring hetero atoms
- C07D293/10—Heterocyclic compounds containing rings having nitrogen and selenium or nitrogen and tellurium, with or without oxygen or sulfur atoms, as the ring hetero atoms condensed with carbocyclic rings or ring systems
- C07D293/12—Selenazoles; Hydrogenated selenazoles
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
Substituted thiazoles and selenazoles are prepared from o-nitrohalogenaryls wherein no substituent is present in position oto the halogen atom, by converting such bodies to an o-dinitrodiaryldisulphide (or diselenide), reducing this product by treating first with an alkali sulphide and then with an alkali hydrosulphite and finally reacting the reduction product with a reagent such as an acyl halide or an organic acid or anhydride to form the substituted thiazole. In examples 4-brom-5-nitroveratrole is heated with polysulphide solution to give 2 . 2<1> - dinitro - 4 . 5 : 4<1> . 5<1> - tetramethoxydiphenyl disulphide, this product was then reduced by heating with sodium sulphide followed by addition of sodium hydrosulphite to complete reduction and the o-aminothiophenol derivative condensed with acetic anhydride to give 1-methyl-4 : 5-dimethoxy-benzthiazole. In similar manner o-chloronitrobenzene is converted to 1-methylbenzthiazole, 4-bromo-5-nitrocatechol methylene ether (prepared by nitrating bromopiperonal) to 1-methyl-4 . 5 - dioxymethylenebenzthiazole, 4 - bromo - 3 - nitro - N - dimethylaniline to 1 - methyl - 4 - dimethylaminobenzthiazole, and 3 - nitro - 4 - bromo - N - diethylaniline to 1 - methyl - 4 - diethylaminobenzthiazole. In a further example 4 - bromo - 5 - nitrocatechol methylene ether is treated with sodium selenide and powdered selenium, the diselenide so obtained is reduced with sodium sulphide followed by sodium hydrosulphite and the product condensed with acetic anhydride to give 1-methyl-4.5-dioxy-methylenebenzselenazole. By using in these examples propionic or other anhydride or benzoic or other anhydride in place of acetic anhydride, 1-ethyl &c. or 1-phenyl &c. substituted bodies are obtained. Reference is made in the Provisional Specification to the use as starting materials of 6-bromo-5-nitroveratrol, 3 - bromo - 4 - nitro - 1 - ethoxynaphthalene, 9 - bromo - 10 - nitrophenanthrene, 4 - bromo - 5 - nitroacenaphthene. The products are of use in the manufacture of cyanine or carbocyanine dyes. The prior art in Specification 388,204, J. American Chem. Socy., 49, page 1749 et seq, and Berichte 46, page 93 et seq is referred to.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB3064732A GB410088A (en) | 1932-10-31 | 1932-10-31 | Improvements in or relating to methods for the preparation of substituted thiazoles or selenazoles |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB3064732A GB410088A (en) | 1932-10-31 | 1932-10-31 | Improvements in or relating to methods for the preparation of substituted thiazoles or selenazoles |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB410088A true GB410088A (en) | 1934-04-30 |
Family
ID=10310905
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB3064732A Expired GB410088A (en) | 1932-10-31 | 1932-10-31 | Improvements in or relating to methods for the preparation of substituted thiazoles or selenazoles |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB410088A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2515913A (en) * | 1946-11-22 | 1950-07-18 | Eastman Kodak Co | 2-methyl-5-phenylbenzothiazole and quaternary salts thereof |
| EP0116827A2 (en) * | 1983-01-21 | 1984-08-29 | Bayer Ag | Process for the preparation of benzothiazoles |
-
1932
- 1932-10-31 GB GB3064732A patent/GB410088A/en not_active Expired
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2515913A (en) * | 1946-11-22 | 1950-07-18 | Eastman Kodak Co | 2-methyl-5-phenylbenzothiazole and quaternary salts thereof |
| EP0116827A2 (en) * | 1983-01-21 | 1984-08-29 | Bayer Ag | Process for the preparation of benzothiazoles |
| EP0116827A3 (en) * | 1983-01-21 | 1986-01-08 | Bayer Ag | Process for the preparation of benzothiazoles |
| US4808723A (en) * | 1983-01-21 | 1989-02-28 | Bayer Aktiengesellschaft | Process for the preparation of benzothiazoles |
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