GB986571A - Method for the preparation of optical sensitizers - Google Patents

Method for the preparation of optical sensitizers

Info

Publication number
GB986571A
GB986571A GB1907161A GB1907161A GB986571A GB 986571 A GB986571 A GB 986571A GB 1907161 A GB1907161 A GB 1907161A GB 1907161 A GB1907161 A GB 1907161A GB 986571 A GB986571 A GB 986571A
Authority
GB
United Kingdom
Prior art keywords
methyl
methylmercapto
nitro
dimethyl sulphate
group
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
Application number
GB1907161A
Inventor
Henri Depoorter
Marcel Jan Libeer
Gerrit Godfried Van Mierlo
Jean Marie Nys
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Gevaert Photo Producten NV
Original Assignee
Gevaert Photo Producten NV
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Gevaert Photo Producten NV filed Critical Gevaert Photo Producten NV
Priority to GB1907161A priority Critical patent/GB986571A/en
Publication of GB986571A publication Critical patent/GB986571A/en
Expired legal-status Critical Current

Links

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
    • C09B23/02—Methine or polymethine dyes, e.g. cyanine dyes the polymethine chain containing an odd number of >CH- or >C[alkyl]- groups
    • C09B23/04—Methine or polymethine dyes, e.g. cyanine dyes the polymethine chain containing an odd number of >CH- or >C[alkyl]- groups one >CH- group, e.g. cyanines, isocyanines, pseudocyanines
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
    • C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
    • C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
    • C07D235/24—Benzimidazoles; Hydrogenated benzimidazoles 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 in position 2
    • C07D235/28—Sulfur atoms
    • 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
    • C09B23/102—The polymethine chain containing an even number of >CH- groups two heterocyclic rings linked carbon-to-carbon

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Cosmetics (AREA)

Abstract

1 - Methyl - 2 - methylmercapto - 7 - carbethoxybenzimidazole is prepared by first refluxing 2-bromo-3-nitrobenzoic acid with thionyl chloride and then with ethanol to give 2-bromo-3-nitroethylbenzoate, refluxing this with methylamine to give 2 - nitro - 6 - carbethoxy - N - methylaniline, reducing the nitro group to the corresponding amine and cyclizing with carbon disulphide in potassium hydroxide to give 1 - methyl - 2 - mercapto - 7 - carbethoxy - benzimidazole. This is then dissolved in sodium hydroxide and treated with dimethyl sulphate. The product may be quaternated by heating with further dimethyl sulphate. 1 - Methyl - 2 - methylmercapto - 5 - (N - methylsulphamyl)-benzimidazole is similarly prepared by first preparing 2 - nitro - 4 - (N - methylsulphamyl)-N-methylaniline by treating 3-nitro-4-chlorobenzenesulphochloride with methylamine, and then reducing, cyclizing with carbon disulphide and methylating as above, the methylation being carried out in N sodium hydroxide. If 2N sodium hydroxide and excess dimethyl sulphate are used for the methylation, 1-methyl-2 - methylmercapto - 5 - (N - dimethylsulphamyl)-benzimidazole is obtained. Either of these 2-methylmercapto-benzimidazoles may be quaternated by heating with dimethyl sulphate. Specifications 955,962, 955,964, 975,504, 981,451 and 981,453 are referred to.ALSO:Mono-methine and merocyanine dyes are prepared by condensing a 2-methylmercapto benzimidazolium salt having a 7-carbethoxy or 5-sulphamyl or 5-N-alkylsubstituted sulphamyl group, with a heterocyclic quaternary ammonium salt having a reactive a - or g -methyl group or with a heterocyclic ketomethylene compound respectively. The N-alkyl-sulphamyl group may be N-methylsulphamyl, N-dimethylsulphamyl or N-ethylsulphamyl. Examples are given wherein the heterocyclic quaternary salt is 1,3-diethyl-2-methyl - 5 - carbethoxybenzimidazolium iodide or the corresponding 5,6-dichlorobenzimidazolium iodide, and wherein the ketomethylene compound is N-ethylrhodanine or N-allylrhodanine. Specifications 955,962, 955,964, 975,504, 981,451 and 981,453 are referred to.
GB1907161A 1961-05-26 1961-05-26 Method for the preparation of optical sensitizers Expired GB986571A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB1907161A GB986571A (en) 1961-05-26 1961-05-26 Method for the preparation of optical sensitizers

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB1907161A GB986571A (en) 1961-05-26 1961-05-26 Method for the preparation of optical sensitizers

Publications (1)

Publication Number Publication Date
GB986571A true GB986571A (en) 1965-03-17

Family

ID=10123282

Family Applications (1)

Application Number Title Priority Date Filing Date
GB1907161A Expired GB986571A (en) 1961-05-26 1961-05-26 Method for the preparation of optical sensitizers

Country Status (1)

Country Link
GB (1) GB986571A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3438774A (en) * 1964-08-25 1969-04-15 Agfa Gevaert Nv Light-sensitive compositions containing methine dyes having a benzothiazole nucleus substituted with a sulfonamido group

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3438774A (en) * 1964-08-25 1969-04-15 Agfa Gevaert Nv Light-sensitive compositions containing methine dyes having a benzothiazole nucleus substituted with a sulfonamido group

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