GB1073228A - Compounds containing a dicarboximido group - Google Patents

Compounds containing a dicarboximido group

Info

Publication number
GB1073228A
GB1073228A GB3414266A GB3414266A GB1073228A GB 1073228 A GB1073228 A GB 1073228A GB 3414266 A GB3414266 A GB 3414266A GB 3414266 A GB3414266 A GB 3414266A GB 1073228 A GB1073228 A GB 1073228A
Authority
GB
United Kingdom
Prior art keywords
ethyl
toluidine
yield
succinimidoethyl
heated
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
GB3414266A
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.)
Eastman Kodak Co
Original Assignee
Eastman Kodak 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
Priority claimed from US232239A external-priority patent/US3161631A/en
Priority claimed from US236135A external-priority patent/US3148178A/en
Priority claimed from US240716A external-priority patent/US3148180A/en
Priority claimed from US250784A external-priority patent/US3213081A/en
Application filed by Eastman Kodak Co filed Critical Eastman Kodak Co
Publication of GB1073228A publication Critical patent/GB1073228A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
    • C07D207/34—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two 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
    • C07D207/36—Oxygen or sulfur atoms
    • C07D207/40—2,5-Pyrrolidine-diones
    • C07D207/404—2,5-Pyrrolidine-diones with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms, e.g. succinimide
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/44—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having three double bonds between ring members or between ring members and non-ring members
    • C07D207/444—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having three double bonds between ring members or between ring members and non-ring members having two doubly-bound oxygen atoms directly attached in positions 2 and 5
    • C07D207/448—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having three double bonds between ring members or between ring members and non-ring members having two doubly-bound oxygen atoms directly attached in positions 2 and 5 with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms, e.g. maleimide
    • C07D207/452—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having three double bonds between ring members or between ring members and non-ring members having two doubly-bound oxygen atoms directly attached in positions 2 and 5 with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms, e.g. maleimide with hydrocarbon radicals, substituted by hetero atoms, directly attached to the ring nitrogen atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/44—Iso-indoles; Hydrogenated iso-indoles
    • C07D209/48—Iso-indoles; Hydrogenated iso-indoles with oxygen atoms in positions 1 and 3, e.g. phthalimide
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/56—Ring systems containing three or more rings
    • C07D209/58—[b]- or [c]-condensed
    • C07D209/72—4,7-Endo-alkylene-iso-indoles
    • C07D209/76—4,7-Endo-alkylene-iso-indoles with oxygen atoms in positions 1 and 3
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D211/80—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
    • C07D211/84—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two 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 directly attached to ring carbon atoms
    • C07D211/86—Oxygen atoms
    • C07D211/88—Oxygen atoms attached in positions 2 and 6, e.g. glutarimide
    • 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
    • C09B29/00—Monoazo dyes prepared by diazotising and coupling
    • C09B29/0025—Monoazo dyes prepared by diazotising and coupling from diazotized amino heterocyclic compounds
    • 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
    • C09B29/00—Monoazo dyes prepared by diazotising and coupling
    • C09B29/06—Monoazo dyes prepared by diazotising and coupling from coupling components containing amino as the only directing group
    • C09B29/08—Amino benzenes

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Indole Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)

Abstract

Compounds of formula <FORM:1073228/C2/1> wherein R1 is H or a C1- 4 alkyl group which may be substituted, R2 is phenylene which may be substituted, R3 is an alkylene group and Y represents the atoms necessary to complete a dicarboximido group are prepared by condensing a dicarboxylic acid anhydride with an aminoalkylaniline. In examples: (1) N-b -aminoethyl - N - ethyl - m - toluidine is heated with phthalic anhydride to yield N-[2-(N-ethyl - m - toluidinyl) ethyl] - phthalimide and N - [2 - (N - ethyl - m - toluidinyl) ethyl]-succinimide or -tetrahydrophthalimide or -bicyclo - [2,2,1] - 5 - heptene - 2,3 - dicarboximide or -tetrachlorophthalimide or -4-carboxyphthalimide or -3-nitrophthalimide or -cyclohexane-1,2-dicarboximide or -citraconimide or -glutarimide are similarly prepared; (7) N-[2 -(N - ethyl - m - toluidinyl) ethyl] - 3 - aminophthalimide is prepared by reduction of the nitro compound; (9) N-[2-(N-ethyl-m-toluidonyl) ethyl] - bicyclo - [2,2,1] - 5 - heptene-2,3-dicarboximide is heated to give off cyclopentadiene and yield N-b -maleimidoethyl-N-ethyl - m - toluidine; (11) N - b - aminoethyl-N-ethyl-aniline is heated with succinic anhydride to yield N-[2-(N-ethylanilinyl) ethyl]-succinimide and N-b -succinimidoethyl-o- or -m-toluidine are similarly prepared; (15) N-b -succinimidoethyl-m-toluidine is heated with ethylene oxide to yield N-2-hydroxyethyl-N-b - succinimidoethyl - m - toluidine which is further reacted with acetic anhydride to yield the N-2-acetoxyethyl compound; (17) N-b -succinimidoethyl-m-toluidine is reacted with acrylonitrile to give N-b -cyanoethyl-N-b -succinimido - ethyl - m - toluidine or with epichlorohydrin to yield N-a -chloro-b -hydroxypropyl - N - b - succinimidoethyl - m - toluidine. Reference has been directed by the Comptroller to Specification 954,814.
GB3414266A 1962-01-07 1963-10-18 Compounds containing a dicarboximido group Expired GB1073228A (en)

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
US24958862A 1962-01-07 1962-01-07
US232239A US3161631A (en) 1962-10-22 1962-10-22 Benzothiazole azo compounds containing a dicarboximido radical
US236135A US3148178A (en) 1962-11-07 1962-11-07 Azo compounds containing a dicarboximido radical
US240716A US3148180A (en) 1962-11-28 1962-11-28 Thiazole azo compounds
US250784A US3213081A (en) 1963-01-11 1963-01-11 Benzothiazole azo compounds

Publications (1)

Publication Number Publication Date
GB1073228A true GB1073228A (en) 1967-06-21

Family

ID=27539991

Family Applications (2)

Application Number Title Priority Date Filing Date
GB3414366A Expired GB1073229A (en) 1962-01-07 1963-10-18 Compounds containing a dicarboximido group
GB3414266A Expired GB1073228A (en) 1962-01-07 1963-10-18 Compounds containing a dicarboximido group

Family Applications Before (1)

Application Number Title Priority Date Filing Date
GB3414366A Expired GB1073229A (en) 1962-01-07 1963-10-18 Compounds containing a dicarboximido group

Country Status (2)

Country Link
BE (1) BE661211A (en)
GB (2) GB1073229A (en)

Also Published As

Publication number Publication date
GB1073229A (en) 1967-06-21
BE661211A (en)

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