GB693540A - Process of chlorinating hydroxy triazines with thionyl chloride - Google Patents

Process of chlorinating hydroxy triazines with thionyl chloride

Info

Publication number
GB693540A
GB693540A GB20232/51A GB2023251A GB693540A GB 693540 A GB693540 A GB 693540A GB 20232/51 A GB20232/51 A GB 20232/51A GB 2023251 A GB2023251 A GB 2023251A GB 693540 A GB693540 A GB 693540A
Authority
GB
United Kingdom
Prior art keywords
triazine
triazines
hydroxy
prepared
dihydroxy
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
GB20232/51A
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.)
Wyeth Holdings LLC
Original Assignee
American Cyanamid Co
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 American Cyanamid Co filed Critical American Cyanamid Co
Publication of GB693540A publication Critical patent/GB693540A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
    • C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
    • C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
    • C07D251/26—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with only hetero atoms directly attached to ring carbon atoms
    • C07D251/40—Nitrogen atoms
    • C07D251/54—Three nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
    • C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
    • C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
    • C07D251/14—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom
    • C07D251/24—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom to three ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
    • C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
    • C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
    • C07D251/26—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with only hetero atoms directly attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
    • C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
    • C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
    • C07D251/26—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with only hetero atoms directly attached to ring carbon atoms
    • C07D251/40—Nitrogen atoms
    • C07D251/54—Three nitrogen atoms
    • C07D251/70—Other substituted melamines
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D253/00—Heterocyclic compounds containing six-membered rings having three nitrogen atoms as the only ring hetero atoms, not provided for by group C07D251/00
    • C07D253/02—Heterocyclic compounds containing six-membered rings having three nitrogen atoms as the only ring hetero atoms, not provided for by group C07D251/00 not condensed with other rings
    • C07D253/06—1,2,4-Triazines
    • C07D253/065—1,2,4-Triazines having three double bonds between ring members or between ring members and non-ring members
    • C07D253/07—1,2,4-Triazines having 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
    • C07D253/075—Two hetero atoms, in positions 3 and 5

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Compositions Of Macromolecular Compounds (AREA)

Abstract

Chlorinated triazines are prepared by heating a hydroxy triazine in an inert organic solvent with thionyl chloride, preferably at a temperature of 110-160 DEG C., e.g. by refluxing in a suitable solvent. Optionally phosphorus pentachloride may be present as catalyst, a suitable amount being from 0.05-0.1 mol. per mol. of hydroxy triazine. Excess thionyl chloride may be removed after the reaction, by vacuum distillation. Suitable solvents are hydrocarbons and their halogenated and nitrated derivatives. Specified triazines are the 3 : 5-dihydroxy-6-phenyl-, 3-hydroxy-5 : 6-diphenyl-, 3 : 5-dihydroxy-6-methyl- and 3-hydroxy-5 : 6-bis-(p-anisyl)-, 1 : 2 : 4-triazines and the 2 : 4 : 6-trihydroxy-, 6-hydroxy-2 : 4-diphenyl- and 6-hydroxy-2 : 4-di-p-tolyl-, 1 : 3 : 5-triazines and particularly the 2-alkyl- or aryl-4 : 6-dihydroxy-1 : 3 : 5-triazines. The chlorinated triazines or the reaction mixture obtained from the chlorination may be reacted with an aminoanthraquinone to give a dye. In examples there are prepared according to the invention (1) 2-o-methoxyphenyl - 4 : 6 - dichloro - 1 : 3 : 5 - triazine; (2) 2 - o - tolyl - 4 : 6 - dichloro - 1 : 3 : 5 - triazine; (3) a solution of 2-phenyl-4 : 6-dichloro-1 : 3 : 5-triazine and (4) 2-chloro-4 : 6-diphenyl-1 : 3 : 5-triazine. Guanamides.-o - Methoxyphenyl - dihydroxy - triazine and o-methylphenyl-dihydroxy-triazine (guanamides) are prepared by treating o-methoxybenzoyl- or o-methylbenzoyl biuret with aqueous potassium hydroxide. Biurets.-o-Methoxybenzoyl- and o-methylbenzoyl-biuret are prepared by treating the corresponding substituted benzoyl dicyandiamides with dilute hydrochloric acid. Dicyandiamides.-o-Methoxybenzoyl- and o-methylbenzoyl-dicyandiamide are prepared by condensing the corresponding substituted benzoyl chloride with dicyandiamide.ALSO:Anthraquinone dyestuffs of the formul <FORM:0693540/IV (c)/1> and <FORM:0693540/IV (c)/2> are prepared by (1) reacting 1-aminoanthraquinone with 6 - (o - methoxyphenyl) - 2 : 4-dichloro - 1 : 3 : 5 - triazine in o - dichlorobenzene or nitrobenzene, and (2) reacting 4-methoxy - 1 - aminoanthraquinone with 6-phenyl - 2 : 4 - dichloro - 1 : 3 : 5 - triazine in nitrobenzene (see Group IV (b), for preparation of the triazines).
GB20232/51A 1951-07-10 1951-08-28 Process of chlorinating hydroxy triazines with thionyl chloride Expired GB693540A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US693540XA 1951-07-10 1951-07-10

Publications (1)

Publication Number Publication Date
GB693540A true GB693540A (en) 1953-07-01

Family

ID=22088406

Family Applications (1)

Application Number Title Priority Date Filing Date
GB20232/51A Expired GB693540A (en) 1951-07-10 1951-08-28 Process of chlorinating hydroxy triazines with thionyl chloride

Country Status (1)

Country Link
GB (1) GB693540A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3365452A (en) * 1960-11-26 1968-01-23 Basf Ag Process for production of chlorodiazines and chlorotriazines

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3365452A (en) * 1960-11-26 1968-01-23 Basf Ag Process for production of chlorodiazines and chlorotriazines

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