GB691520A - o-hydroxyaryl dihalotriazines - Google Patents

o-hydroxyaryl dihalotriazines

Info

Publication number
GB691520A
GB691520A GB23500/51A GB2350051A GB691520A GB 691520 A GB691520 A GB 691520A GB 23500/51 A GB23500/51 A GB 23500/51A GB 2350051 A GB2350051 A GB 2350051A GB 691520 A GB691520 A GB 691520A
Authority
GB
United Kingdom
Prior art keywords
methoxy
dichlorotriazine
methoxybenzoic
naphthoic
acid
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
GB23500/51A
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 GB691520A publication Critical patent/GB691520A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
    • C07C49/84—Ketones containing a keto group bound to a six-membered aromatic ring containing ether groups, groups, groups, or groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C43/00—Ethers; Compounds having groups, groups or groups
    • C07C43/02—Ethers
    • C07C43/20—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring
    • C07C43/225—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring containing halogen

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

The invention comprises 2-(o-hydroxy-aryl)-4 : 6-dichloro- and -dibromo-triazines and their production by de-alkylation of the corresponding o-alkoxyaryl compounds, using hydrogen halide in an inert organic solvent at 100-200 DEG C. The alkoxy group contains 1-5 carbon atoms. Exchange of halogen atoms in the ring may take place. The starting materials are made by condensing o-alkoxyaroyl chlorides with dicyandiamide, hydrolysing the products with acid to o-alkoxyaroyl-biurets, alkaline ring-closure of the latter to 2-(o-alkoxyaryl)-4 : 6-dihydroxytriazines and final treatment with phosphorus halides. Examples show the successive production of (1) o-anisoyldicyandiamide, o-anisoylbiuret, o-anisoguanamide, o-anisyl-dichlorotriazine and o-hydroxyphenyl-dichlorotriazine; (2) 2 - methoxy - 5 - chlorobenzoyl chloride (from the acid and thionyl chloride), 2-methoxy-5 - chlorobenzoyldicyandiamide, 2 - methoxy - 5 - chlorobenzoylbiuret, 2 - methoxy - 5 - chlorobenzoguanamide, 2 - methoxy - 5 - chlorophenyl-dichlorotriazine and 2-hydroxy-5-chlorophenyl - dibromotriazine (by halogen interchange, hydrogen bromide being used). In a further example the o-hydroxyphenyl-dibromotriazine which is produced intermediately in (1) is isolated as such. Other specified starting materials are the acid chlorides of o-ethoxybenzoic, o-propoxybenzoic, 4-chloro-2-methoxybenzoic, 5 - bromo - 2 - propoxybenzoic, 4 - methyl - 2 - methoxybenzoic, 5 - nitro - 4 - methyl - 2 - methoxybenzoic, 1 - methoxy - 2 - naphthoic, 2 - methoxy - 3 - naphthoic, 4 - nitro - 1 - methoxy - 2 - naphthoic, 1 - methoxyphenanthrene - 2 - carboxylic and 3 - methoxyphenanthrene-2-carboxylic acids. The products are intermediates for anthraquinone vat dyes, cf. Specification 691,506.
GB23500/51A 1951-05-23 1951-10-09 o-hydroxyaryl dihalotriazines Expired GB691520A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US691520XA 1951-05-23 1951-05-23

Publications (1)

Publication Number Publication Date
GB691520A true GB691520A (en) 1953-05-13

Family

ID=22087085

Family Applications (1)

Application Number Title Priority Date Filing Date
GB23500/51A Expired GB691520A (en) 1951-05-23 1951-10-09 o-hydroxyaryl dihalotriazines

Country Status (1)

Country Link
GB (1) GB691520A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3270016A (en) * 1963-01-25 1966-08-30 Ciba Ltd Aryl-1, 3, 5-triazines

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3270016A (en) * 1963-01-25 1966-08-30 Ciba Ltd Aryl-1, 3, 5-triazines

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