GB928897A - Production of n-brominated organic compounds - Google Patents

Production of n-brominated organic compounds

Info

Publication number
GB928897A
GB928897A GB3022660A GB3022660A GB928897A GB 928897 A GB928897 A GB 928897A GB 3022660 A GB3022660 A GB 3022660A GB 3022660 A GB3022660 A GB 3022660A GB 928897 A GB928897 A GB 928897A
Authority
GB
United Kingdom
Prior art keywords
dibromo
bromo
compounds
dibromobiuret
bromoacetamide
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
GB3022660A
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.)
RICHARD CAMPBELL WAUGH
THOMAS DROKE WAUGH
Original Assignee
RICHARD CAMPBELL WAUGH
THOMAS DROKE WAUGH
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 RICHARD CAMPBELL WAUGH, THOMAS DROKE WAUGH filed Critical RICHARD CAMPBELL WAUGH
Priority to GB3022660A priority Critical patent/GB928897A/en
Publication of GB928897A publication Critical patent/GB928897A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
    • C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B39/00—Halogenation
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C275/00—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
    • C07C275/66—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to halogen atoms or to nitro or nitroso groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
    • C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings 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
    • C07D233/72—Two oxygen atoms, e.g. hydantoin
    • C07D233/80—Two oxygen atoms, e.g. hydantoin with hetero atoms or acyl radicals directly attached to ring nitrogen atoms
    • C07D233/82—Halogen atoms

Abstract

N-Brominated organic compounds are prepared by treating an organic compound selected from imides of succinic, glutaric and phthalic acid and of alkyl and aryl succinic and glutaric acids; compounds RCONH2, where R is hydrogen, alkyl, cycloalkylalkyl, carboxyethyl, phenyl, alkylphenyl or phenylalkyl; hydantoins and 5,5-dialkyl, aryl and cycloaliphatic hydantoins; urea, biuret, oxamide, terephthalamide; and compounds H2NCO(CH2)nCONH2, where n is 2, 3 or 4; with bromine in an aqueous solution containing bromate ion at an acid pH. Chloride ion is also preferably present. The invention also comprises the compounds N,N1-dibromourea and 1,5-dibromo biuret. Examples prepare (1)-(5) N-bromosuccinimide, (6) N-bromoglutarimide, (7) N-bromophthalimide, (8) N-bromo-b -methylglutarimide, (9) N-bromo-a -phenylsuccinimide, (10) N-bromo-a -methylsuccinimide, (11) N-bromoformamide, (12), (13) N-bromoacetamide, (14) N-bromopropionamide, (15) N-bromobutyramide, (16) N-bromovaleramide, (17) N-bromobenzamide, (18) N-bromo-o-toluamide, (19) N-bromophenylacetamide, (20) N-bromocyclopentylpropionamide, (21) N,N1-dibromooxamide, (22) N,N1-dibromosuccindiamide, (23) N,N1-dibromoadipamide, (24) N,N1-dibrometerephthalamide, (25) succinic acid N-bromo-monoamide, (26) N,N1-dibromourea, (27) dibromobiuret, (28) 1,3-dibromohydantoin, (29) 1,3-dibromo-5,5-dimethylhydantoin, (30) 1,3-dibromo- 5-methyl-5-ethylhydantoin, (31) 1,3-dibromo- 5-methyl-5-isobutylhydantoin, (32) 1,3-dibromo-5,5-diphenylhydantoin, (33) 1,3-dibromo- 5,5-pentamethylenehydantoin, and (34) monobromo-5,5-dimethylhydantoin. Cyclohexene with N-bromosuccinimide or dibromobiuret in CCl4 gives 3-bromocyclohexene; with N-bromoacetamide it gives cyclohexenedibromide. Styrene with N-bromoacetamide or dibromobiuret in CCl4 gives styrene dibromide.
GB3022660A 1960-09-01 1960-09-01 Production of n-brominated organic compounds Expired GB928897A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB3022660A GB928897A (en) 1960-09-01 1960-09-01 Production of n-brominated organic compounds

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB3022660A GB928897A (en) 1960-09-01 1960-09-01 Production of n-brominated organic compounds

Publications (1)

Publication Number Publication Date
GB928897A true GB928897A (en) 1963-06-19

Family

ID=10304282

Family Applications (1)

Application Number Title Priority Date Filing Date
GB3022660A Expired GB928897A (en) 1960-09-01 1960-09-01 Production of n-brominated organic compounds

Country Status (1)

Country Link
GB (1) GB928897A (en)

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4374220A (en) 1968-09-18 1983-02-15 Raychem Corporation Imide flame retardants and compositions containing them
US4535170A (en) * 1968-09-18 1985-08-13 Raychem Corporation Flame retardants and compositions containing them
US4581396A (en) * 1968-09-18 1986-04-08 Raychem Corporation Flame retardants and compositions containing them
US4644066A (en) * 1968-09-18 1987-02-17 Raychem Corporation Flame retardants and compositions containing them
US5565576A (en) * 1994-10-27 1996-10-15 Lonza Inc. Halohydantoin and fatty amide composition for compaction, process of compacting and product produced thereby
CN102219637A (en) * 2011-04-27 2011-10-19 浙江医药股份有限公司新昌制药厂 Method for isomerizing 1,4-dichloro-2-butylene from cis-form to trans-form

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4374220A (en) 1968-09-18 1983-02-15 Raychem Corporation Imide flame retardants and compositions containing them
US4535170A (en) * 1968-09-18 1985-08-13 Raychem Corporation Flame retardants and compositions containing them
US4581396A (en) * 1968-09-18 1986-04-08 Raychem Corporation Flame retardants and compositions containing them
US4644066A (en) * 1968-09-18 1987-02-17 Raychem Corporation Flame retardants and compositions containing them
US5565576A (en) * 1994-10-27 1996-10-15 Lonza Inc. Halohydantoin and fatty amide composition for compaction, process of compacting and product produced thereby
CN102219637A (en) * 2011-04-27 2011-10-19 浙江医药股份有限公司新昌制药厂 Method for isomerizing 1,4-dichloro-2-butylene from cis-form to trans-form

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