GB980232A - Improvements relating to cyclic azo compounds - Google Patents

Improvements relating to cyclic azo compounds

Info

Publication number
GB980232A
GB980232A GB2051261A GB2051261A GB980232A GB 980232 A GB980232 A GB 980232A GB 2051261 A GB2051261 A GB 2051261A GB 2051261 A GB2051261 A GB 2051261A GB 980232 A GB980232 A GB 980232A
Authority
GB
United Kingdom
Prior art keywords
amino
nitro
hydroxy
reducing
compound
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
GB2051261A
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.)
Novartis AG
Original Assignee
JR Geigy AG
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 CH651960A external-priority patent/CH384750A/en
Priority claimed from CH902960A external-priority patent/CH401072A/en
Priority claimed from CH550461A external-priority patent/CH402228A/en
Application filed by JR Geigy AG filed Critical JR Geigy AG
Publication of GB980232A publication Critical patent/GB980232A/en
Expired legal-status Critical Current

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D273/00Heterocyclic compounds containing rings having nitrogen and oxygen atoms as the only ring hetero atoms, not provided for by groups C07D261/00 - C07D271/00
    • C07D273/02Heterocyclic compounds containing rings having nitrogen and oxygen atoms as the only ring hetero atoms, not provided for by groups C07D261/00 - C07D271/00 having two nitrogen atoms and only one oxygen atom
    • C07D273/06Seven-membered rings
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D285/00Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
    • C07D285/36Seven-membered rings
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D285/00Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
    • C07D285/38Eight-membered rings
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09BORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B37/00Azo dyes prepared by coupling the diazotised amine with itself
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09BORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B39/00Other azo dyes prepared by diazotising and coupling
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09BORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B43/00Preparation of azo dyes from other azo compounds
    • C09B43/003Cyclisation of azo dyes; Condensation of azo dyes with formation of ring, e.g. of azopyrazolone dyes

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Heat Sensitive Colour Forming Recording (AREA)

Abstract

2 - Amino - 4 - methylsulphonyl - 31 - hydroxydiphenyl ether is prepared by reacting 1-chloro-2 - nitrobenzene - 4 - methyl sulphone with resorcin in the presence of sodium carbonate, copper powder and n-amyl alcohol to obtain 2-nitro - 4 - methylsulphonyl - 31 - hydroxydiphenyl ether and reducing the latter in aqueous solution with iron. 2 - Amino - 4 - methylsulphonyl - 31 - dimethylamino-diphenyl ether is obtained similarly using 3 - hydroxy - N,N - diethylaminobenzene instead of resorcin. 2 - Amino - 31 - hydroxy - diphenylthioether is obtained by reacting m-aminothiophenol with o-nitrochlorobenzene, treating the product to obtain the hydrochloride of 2-nitro-31-aminodiphenylthioether, diazotizing the latter, treating with hot aqueous sulphuric acid and reducing the product by catalytic hydrogenation or the B<\>echamp method. 2 - Amino - 4 - methylsulphonyl - 31 - acetylamino-diphenylthioether is obtained by reacting 1 - methylsulphonyl - 3 - nitro - 4 - chlorobenzene with m-aminothiophenol, acetylating the product and reducing with hydrogen and Raney nickel. The compound of the formula <FORM:0980232/C2/1> is obtained by condensing o-nitrobenzene sulphonic acid chloride and 1-N,N-diethylamino-3-aminobenzene and reducing the nitro compound to the amine by reduction in aqueous/alcoholic solution with iron. In a further process the intermediate is methylated with methyl sulphate before reduction of the nitro group. The compounds of the formulae <FORM:0980232/C2/2> and <FORM:0980232/C2/3> are obtained by condensing appropriately substituted benzenes with the appropriate nitrobenzene sulphonic chloride and reducing the nitro group in the product to an amino group. The compound of the formula <FORM:0980232/C2/4> is obtained by condensing 2-nitrocarboxylic acid chloride with 1-methylamino-3-diethylaminobenzene and reducing the nitro group in the product to an amino group.ALSO:The invention comprises cyclic azo compounds corresponding to the general formula <FORM:0980232/C4-C5/1> wherein R represents the bridging members <FORM:0980232/C4-C5/2> where Y represents hydrogen or a possibly substituted hydrocarbon radical and X represents a secondary or tertiary amino group, a carboxylic acid acylamin, carbonic acid monoester acylamino, a sulphonylamino, hydroxy or alkoxy group and A and B can contain additional substituents and, possibly, fused ring systems, and a process for the preparation thereof comprising diazotizing an o-amino diaryl compound of the general formula <FORM:0980232/C4-C5/3> wherein R, X, Y, A and B have the meanings given above under the condition that the para-position with respect to the substituent X in ring A is unsubstituted, and coupling to form the cyclic compound. Representative of the large numbers of starting materials specified are 2 - amino - 4 - methyl - sulphonyl - 31-hydroxy-; the corresponding 31-methoxy-31-dimethylamino and 31-acetylamino compounds, 1,3 - diamono - 4,6 - bis - (31 - diethylaminophenoxy) 8 benzene, 3,31 - diamino - 4,41-bis - (311 - diethylaminophenyoxy) - diphenylsulphone, 2 - amino - 31 - hydroxy - diphenyl thioether and the corresponding 31-dimethylamino compound 2 - aminobenzene - sulphonic acid or carboxylic acid-N-[31-(N1,N1-dimethyl amino) - phenyl] - N - methylamide. Additional substituent present in rings A and B may be secondary or tertiary amino groups, carboxylic acylamino, hydroxy or ether groups, carboxylic acid ester or amide or nitrile groups, sulphonic acid and sulphonamide groups, nitro, trifluoromethyl groups and halogen atoms such as fluorine, chlorine or bromine.
GB2051261A 1960-06-08 1961-07-07 Improvements relating to cyclic azo compounds Expired GB980232A (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
CH651960A CH384750A (en) 1960-06-08 1960-06-08 Process for the preparation of new 2,3: 6,7-diareno-1-oxa-4,5-diazepines
CH902960A CH401072A (en) 1960-06-08 1960-08-10 Process for the preparation of new 2,3: 6,7-diareno-1-thia-4,5-diazepines
CH550461A CH402228A (en) 1960-06-08 1961-05-10 Process for the production of new diareno-triazocines

Publications (1)

Publication Number Publication Date
GB980232A true GB980232A (en) 1965-01-13

Family

ID=27175235

Family Applications (1)

Application Number Title Priority Date Filing Date
GB2051261A Expired GB980232A (en) 1960-06-08 1961-07-07 Improvements relating to cyclic azo compounds

Country Status (5)

Country Link
BE (1) BE604735A (en)
DE (1) DE1220952B (en)
FR (1) FR1292492A (en)
GB (1) GB980232A (en)
NL (1) NL265668A (en)

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6937471B1 (en) 2002-07-11 2005-08-30 Raytheon Company Method and apparatus for removing heat from a circuit
US7000691B1 (en) 2002-07-11 2006-02-21 Raytheon Company Method and apparatus for cooling with coolant at a subambient pressure
US6957550B2 (en) 2003-05-19 2005-10-25 Raytheon Company Method and apparatus for extracting non-condensable gases in a cooling system
US8341965B2 (en) 2004-06-24 2013-01-01 Raytheon Company Method and system for cooling
US7254957B2 (en) 2005-02-15 2007-08-14 Raytheon Company Method and apparatus for cooling with coolant at a subambient pressure
US7908874B2 (en) 2006-05-02 2011-03-22 Raytheon Company Method and apparatus for cooling electronics with a coolant at a subambient pressure
US7907409B2 (en) 2008-03-25 2011-03-15 Raytheon Company Systems and methods for cooling a computing component in a computing rack

Also Published As

Publication number Publication date
DE1220952C2 (en) 1967-01-19
FR1292492A (en) 1962-03-26
DE1220952B (en) 1966-07-14
BE604735A (en) 1961-12-07
NL265668A (en) 1964-07-10

Similar Documents

Publication Publication Date Title
GB980232A (en) Improvements relating to cyclic azo compounds
GB981191A (en) Water-soluble phthalocyanine dyestuffs and process for their manufacture
GB2163154A (en) Diamino tetrafluoroethoxy benzene derivatives and their use as couplers in hair dyeing composition
FI80208B (en) HAORFAERGER.
GB995794A (en)
GB1164797A (en) 6,7-Disubstituted-4-Hydroxyquinoline-3-Carboxylates and Anticoccidial Compositions Containing Them
GB663005A (en) Photographic silver halide emulsions containing non-diffusing azo dyes
GB723382A (en) Light-sensitive diazotype layers and photomechanical printing plates
SE7409683L (en)
US3775442A (en) Process for the manufacture of a triarylmethane compound
GB490364A (en) Improvements in the manufacture and production of amino compounds
CN109020827B (en) Method for synthesizing m-dialkylaminophenol
GB1028564A (en) Water-insoluble monoazo-dyestuffs and process for their manufacture
GB749908A (en) Manufacture of xanthenium compounds
GB811679A (en) Process for the development of photographic images, especially colour images
GB977472A (en) New monoazo compounds containing halogeno-triazinylamino groups
GB441079A (en) Manufacture of intermediates for azo dyes
GB1008171A (en) Improvements relating to monoazo dyestuffs which are difficultly soluble in water, and their use
GB490067A (en) The manufacture of sulphur dyestuffs
McKee et al. Some Derivatives of 3-Amino-4-(1-diethylamino-4-pentylamino)-chlorobenzene
GB960521A (en) Improvements relating to anthraquinone dyestuffs, their production and use
GB430580A (en) Improvements in and relating to the manufacture of azo compounds
GB883297A (en) Improvements in and relating to amines
GB988776A (en) Process for the production of new carbostyril derivatives
GB1068540A (en) Improvements in or relating to azo dyestuffs