GB745070A - Improvements in or relating to basic thymol dimethyl-amino ethyl ethers - Google Patents

Improvements in or relating to basic thymol dimethyl-amino ethyl ethers

Info

Publication number
GB745070A
GB745070A GB11719/53A GB1171953A GB745070A GB 745070 A GB745070 A GB 745070A GB 11719/53 A GB11719/53 A GB 11719/53A GB 1171953 A GB1171953 A GB 1171953A GB 745070 A GB745070 A GB 745070A
Authority
GB
United Kingdom
Prior art keywords
thymol
ether
group
compound
ethyl ethers
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
GB11719/53A
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.)
Veritas Drug Co Ltd
Original Assignee
Veritas Drug Co Ltd
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 Veritas Drug Co Ltd filed Critical Veritas Drug Co Ltd
Priority to GB11719/53A priority Critical patent/GB745070A/en
Publication of GB745070A publication Critical patent/GB745070A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
    • C07C213/02—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton by reactions involving the formation of amino groups from compounds containing hydroxy groups or etherified or esterified hydroxy groups

Landscapes

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

Abstract

The invention comprises basic thymol dimethylamino-ethyl ethers of the general formula <FORM:0745070/IV(a)/1> where R is a hydroxy, alkoxy or acyloxy group. Preferably R is a hydroxy, methoxy or acetoxy group. Such compounds are obtained by treating thymol with sodium nitrite and an acid to form nitroso-thymol, introducing the latter into ammonia, reducing with hydrogen sulphide to form 4-amino thymol, acetylating the 4-aminothymol, converting the resulting 4-acetaminothymol with dimethylaminoethyl chloride into the dimethylaminoethyl ether of 4-acetaminothymol, treating with hydrochloric acid to hydrolyse the 4-acetamino group to an amino group, making the mixture alkaline and extracting with ether, diazotizing the resulting 4-aminothymoxyethyldimethylamine, adding a small quantity of copper sulphate to the diazo compound, boiling, making the mixture alkaline and introducing carbon dioxide form 4-oxythymoxyethyldimethylamine. The product can be acetylated with acetic anhydride and pyridine to form the corresponding 4-acetoxy compound, or methylated with diazomethane in ether to form the 4-methoxy compound. Examples illustrate this method of preparation.
GB11719/53A 1953-04-28 1953-04-28 Improvements in or relating to basic thymol dimethyl-amino ethyl ethers Expired GB745070A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB11719/53A GB745070A (en) 1953-04-28 1953-04-28 Improvements in or relating to basic thymol dimethyl-amino ethyl ethers

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB11719/53A GB745070A (en) 1953-04-28 1953-04-28 Improvements in or relating to basic thymol dimethyl-amino ethyl ethers

Publications (1)

Publication Number Publication Date
GB745070A true GB745070A (en) 1956-02-22

Family

ID=9991421

Family Applications (1)

Application Number Title Priority Date Filing Date
GB11719/53A Expired GB745070A (en) 1953-04-28 1953-04-28 Improvements in or relating to basic thymol dimethyl-amino ethyl ethers

Country Status (1)

Country Link
GB (1) GB745070A (en)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2194427A1 (en) * 1972-08-02 1974-03-01 Warner Lambert Co
US3966779A (en) * 1973-04-30 1976-06-29 Warner-Lambert Company Thymol derivatives and a process for their preparation
FR2503142A1 (en) * 1981-04-06 1982-10-08 Cortial N-Substd. 4-aminoethoxy-2-methyl-5-isopropyl-phenol derivs. - useful as alpha blockers and platelet aggregation inhibitors
EP0062596A1 (en) * 1981-04-06 1982-10-13 Cortial S.A. Derivatives of 4-aminoethoxy-5-isopropyl-2-methyl phenol, process for their preparation and their use as medicines

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2194427A1 (en) * 1972-08-02 1974-03-01 Warner Lambert Co
US3966779A (en) * 1973-04-30 1976-06-29 Warner-Lambert Company Thymol derivatives and a process for their preparation
FR2503142A1 (en) * 1981-04-06 1982-10-08 Cortial N-Substd. 4-aminoethoxy-2-methyl-5-isopropyl-phenol derivs. - useful as alpha blockers and platelet aggregation inhibitors
EP0062596A1 (en) * 1981-04-06 1982-10-13 Cortial S.A. Derivatives of 4-aminoethoxy-5-isopropyl-2-methyl phenol, process for their preparation and their use as medicines

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