GB615006A - Improvements in the manufacture of heterocyclic compounds - Google Patents

Improvements in the manufacture of heterocyclic compounds

Info

Publication number
GB615006A
GB615006A GB2404546A GB2404546A GB615006A GB 615006 A GB615006 A GB 615006A GB 2404546 A GB2404546 A GB 2404546A GB 2404546 A GB2404546 A GB 2404546A GB 615006 A GB615006 A GB 615006A
Authority
GB
United Kingdom
Prior art keywords
give
heated
oxazoline
ethanolamine
phenyl
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
GB2404546A
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.)
Boots Pure Drug Co Ltd
Original Assignee
Boots Pure 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 Boots Pure Drug Co Ltd filed Critical Boots Pure Drug Co Ltd
Priority to GB2404546A priority Critical patent/GB615006A/en
Publication of GB615006A publication Critical patent/GB615006A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
    • C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
    • C07D263/08—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D263/10—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
    • C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
    • C07D263/08—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D263/10—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C07D263/12—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms with radicals containing only hydrogen and carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
    • C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
    • C07D263/08—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D263/10—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C07D263/14—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms with radicals substituted by oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D265/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one oxygen atom as the only ring hetero atoms
    • C07D265/04—1,3-Oxazines; Hydrogenated 1,3-oxazines
    • C07D265/06—1,3-Oxazines; Hydrogenated 1,3-oxazines not condensed with other rings
    • C07D265/08—1,3-Oxazines; Hydrogenated 1,3-oxazines not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)

Abstract

Heterocyclic compounds of the general formula <FORM:0615006/IV(b)/1> where R represents an aralkyl, aryl or heterocyclic group, which may contain other substituents and M represents a polymethylene group containing 2, 3 or 4 methylene groups, are produced by heating an N-substituted amidine of the general formula RC(=NR1).NR2R3 where R1 represents an alkyl or aryl group and R2 and R3 each represent a hydrogen atom or an alkyl or aryl group, with an amino alcohol of the general formula NH2MOH in the presence of sufficient acid to form the normal salt of the amidine. The heterocyclic compound may be formed either as the free base or as the salt, depending on the relative basicities of the bases present. Conveniently, the reaction takes place in the presence of excess of the amino alcohol, in which case the free base of the product is obtained. In examples: (1) N-phenyl-p-methylsulphonylbenzamidine benzene sulphonate is heated with ethanolamine to give 2 - (p - methylsulphonylphenyl) - oxazoline; (2) N-phenyl nonatramidine benzene sulphonate is heated with ethanolamine and the product is treated with picric acid to be isolated as 2-(31 : 41-dimethoxyphenyl)-oxazoline picrate; (3) N : N : N1-trimethylbenzamidine is heated with ethanolamine toluene-p-sulphonate and the product is treated with lithium picrate to give 2-phenyl-oxazoline picrate; (4) N-cyclohexylphenylacetamidine hydrochloride and ethanolamine are treated as in (2) to give 2-benzyloxazoline picrate; (5) N-ethyl-p-methylsulphonyl - benzamidine toluene - p - sulphonate is heated with 2-methyl-2-aminopropanol to give 2 - p - methylsulphonylphenyl - 4 : 4 - dimethyl - oxazoline; and (6) N - phenyl - p - methylsul - phonylbenzamidine hydrochloride is heated with 3-amino-propanol to give 2-p-methylsulphonylphenyl-D 2-dihydro-1 : 3-oxazine.
GB2404546A 1946-08-13 1946-08-13 Improvements in the manufacture of heterocyclic compounds Expired GB615006A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB2404546A GB615006A (en) 1946-08-13 1946-08-13 Improvements in the manufacture of heterocyclic compounds

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB2404546A GB615006A (en) 1946-08-13 1946-08-13 Improvements in the manufacture of heterocyclic compounds

Publications (1)

Publication Number Publication Date
GB615006A true GB615006A (en) 1948-12-31

Family

ID=10205497

Family Applications (1)

Application Number Title Priority Date Filing Date
GB2404546A Expired GB615006A (en) 1946-08-13 1946-08-13 Improvements in the manufacture of heterocyclic compounds

Country Status (1)

Country Link
GB (1) GB615006A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2648664A (en) * 1951-03-23 1953-08-11 Us Agriculture 4,4,6-trimethyl-2-(1-hydroxyethyl)-5,6-dihydro-1,3-4h-oxazine

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2648664A (en) * 1951-03-23 1953-08-11 Us Agriculture 4,4,6-trimethyl-2-(1-hydroxyethyl)-5,6-dihydro-1,3-4h-oxazine

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