GB980232A - Improvements relating to cyclic azo compounds - Google Patents
Improvements relating to cyclic azo compoundsInfo
- 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
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D273/00—Heterocyclic compounds containing rings having nitrogen and oxygen atoms as the only ring hetero atoms, not provided for by groups C07D261/00 - C07D271/00
- C07D273/02—Heterocyclic 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
- C07D273/06—Seven-membered rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
- C07D285/36—Seven-membered rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
- C07D285/38—Eight-membered rings
-
- 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
- C09B37/00—Azo dyes prepared by coupling the diazotised amine with itself
-
- 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
- C09B39/00—Other azo dyes prepared by diazotising and coupling
-
- 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
- C09B43/00—Preparation of azo dyes from other azo compounds
- C09B43/003—Cyclisation 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.
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)
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 |
-
1961
- 1961-06-07 DE DEG32432A patent/DE1220952B/en active Granted
- 1961-06-07 BE BE604735A patent/BE604735A/en unknown
- 1961-06-07 FR FR864182A patent/FR1292492A/fr not_active Expired
- 1961-06-07 NL NL265668D patent/NL265668A/xx unknown
- 1961-07-07 GB GB2051261A patent/GB980232A/en not_active Expired
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 |
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