GB709455A - Water-soluble asymmetric ureas and thioureas and a process for their production - Google Patents
Water-soluble asymmetric ureas and thioureas and a process for their productionInfo
- Publication number
- GB709455A GB709455A GB29268/51A GB2926851A GB709455A GB 709455 A GB709455 A GB 709455A GB 29268/51 A GB29268/51 A GB 29268/51A GB 2926851 A GB2926851 A GB 2926851A GB 709455 A GB709455 A GB 709455A
- Authority
- GB
- United Kingdom
- Prior art keywords
- isocyanate
- amine
- sulphonic acid
- amino
- chloro
- 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
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
- C07C309/01—Sulfonic acids
- C07C309/28—Sulfonic acids having sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C309/45—Sulfonic acids having sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing nitrogen atoms, not being part of nitro or nitroso groups, bound to the carbon skeleton
- C07C309/51—Sulfonic acids having sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing nitrogen atoms, not being part of nitro or nitroso groups, bound to the carbon skeleton at least one of the nitrogen atoms being part of any of the groups, X being a hetero atom, Y being any atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C335/00—Thioureas, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C335/04—Derivatives of thiourea
- C07C335/16—Derivatives of thiourea having nitrogen atoms of thiourea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Condensation products which are asymmetric ureas or thioureas are obtained by treating o-amino-sulphonic acids of the benzene series with aromatic carbonic or thiocarbonic acid derivatives; the products contain one or more trifluoromethyl groups. The same products are obtained by using aromatic carboxylic acid azides or N-halo-amides as acylating agents, or by reacting urethanes of the o-aminosulphonic acids with aromatic amines. Further halogen atoms may be introduced into the products. Suitable carbonic acid derivatives are halides, esters and amides, carbon disulphide, isocyanates and isothiocyanates. In the examples the following are reacted: (1) 3 : 4-dichloraniline - 6 - sulphonic acid and 4 - chloro - 3 - trifluoromethyl-phenyl isocyanate; (2) amine of (1) and 3 : 5-bis-trifluoromethyl-phenyl isocyanate; (3) 4-chloro-3-trifluoromethylaniline-6-sulphonic acid and 3 : 4-dichlorophenyl isocyanate; (4) amine of (3) and isocyanate of (2); (5) amine of (3) and isocyanate of (1); (6) amine of (3) and 3-trifluoromethyl-phenyl isocyanate; (7) 2 - chloro - 5 - trifluoromethylaniline - 6 - sulphonic acid and 2-chloro-5-trifluoromethylphenyl isocyanate; (8) amine of (7) and isocyanate of (1); (9) amine of (7) and isocyanate of (2); (10) 3 : 4-dichloro-6-sulpho-phenylcarbamic phenyl ester and 3-trifluoromethyl-4-chloraniline; (11) amine of (3) and 3 : 4-dichlorobenzoyl azide; (12) amine of (3) and 4-chlorobenzoic chloramide; (13) amine of (3) and 4-chlorophenyl isothiocyanate; (14) 4-amino - 2 : 41 - dichloro - diphenylether - 5 - sulphonic acid and isocyanate of (1); (15) 4-amino-41-chloro-diphenylether-5-sulphonic acid and 3 : 5 - dimethyl - 41 - trifluoromethyl - diphenyl-ether-21-isocyanate; (16) 4-amino-2 : 41 : 51-trichlorodiphenylether-5-sulphonic acid and isocyanate of (1); (17) amine of (14) and 3-trifluoromethylphenyl isothiocyanate; (18) 2 : 41-dichloro - 5 - sulpho - diphenylether - 4 - carbamic phenyl ester and amine of (10); (19) 4-amino - 51 - methyl - diphenylether - 5 - sulphonic acid and amine of (1), the product being chlorinated; (20) 2 - amino - 4 : 41 - dichloro - diphenylether-3-sulphonic acid and isocyanate of (7); (21) 4-amino-21 : 41-dichloro-diphenyl-ether-5-sulphonic acid and isocyanate of (1); (22) amine of (15) and isocyanate of (6); (23) 4-amino - 2 : 21 : 41 - trichloro - diphenylether - 5 - sulphonic acid and isocyanate of (2). Other suitable components and products are listed. The preparation of similar compounds without the trifluoromethyl group is acknowledged, e.g. in Specifications 536,011 and 536,047. The above isocyanates and isothiocyanates are made by known methods from the corresponding amines via the carbamic acid chlorides, for example 4-chloro-3-trifluoromethylphenyl isocyanate. A list of suitable amines is given. The amine of example 7 is made by sulphonation of 2-chloro-5-trifluoromethylaniline. The amine of example 14 is made by condensing p-chlorophenol with 3 : 4-dichloronitrobenzene-6-sulphonic acid and reducing the product. Other amines may be made in the same way. The urethane of example 18 is prepared from the corresponding amine and phenyl chloroformate.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CH709455X | 1950-12-26 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB709455A true GB709455A (en) | 1954-05-26 |
Family
ID=4530650
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB29268/51A Expired GB709455A (en) | 1950-12-26 | 1951-12-13 | Water-soluble asymmetric ureas and thioureas and a process for their production |
Country Status (1)
Country | Link |
---|---|
GB (1) | GB709455A (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2004046090A3 (en) * | 2002-11-21 | 2004-08-19 | Neurosearch As | Aryl ureido derivatives and their medical use |
-
1951
- 1951-12-13 GB GB29268/51A patent/GB709455A/en not_active Expired
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2004046090A3 (en) * | 2002-11-21 | 2004-08-19 | Neurosearch As | Aryl ureido derivatives and their medical use |
JP2006507329A (en) * | 2002-11-21 | 2006-03-02 | ニューロサーチ、アクティーゼルスカブ | Novel arylureidobenzoic acid derivatives and uses thereof |
US7521480B2 (en) | 2002-11-21 | 2009-04-21 | Neurosearch | Aryl ureido benzoic acid derivatives and their use |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
GB742457A (en) | Diisocyanate-modified polyester or polyesteramide elastomers | |
ES471337A1 (en) | Preparation of isocyanate-substituted allophanates and their use for the preparation of lacquers. | |
GB796041A (en) | Polyalkylene ether-polyurethane polymer and elastomeric products obtainable therefrom | |
DE1202785B (en) | Process for the preparation of 1-isocyanato-3- (isocyanatomethyl) -3, 5, 5-trimethylcyclohexane | |
ATE2137T1 (en) | PROCESSES FOR THE PRODUCTION OF ALIPHATIC AND CYCLOALIPHATIC DI- AND POLYURETHANES. | |
US2871226A (en) | Elastomeric condensation products prepared from polyether glycols | |
JPS56103152A (en) | Manufacture of n*oodisubstituted urethane useful for manufacture of isocyanate | |
GB1474984A (en) | Isocyanates | |
GB901377A (en) | The preparation of organic isocyanates | |
KR960022451A (en) | Continuous production method of organic isocyanate | |
GB709455A (en) | Water-soluble asymmetric ureas and thioureas and a process for their production | |
KR910007996A (en) | Method for producing aliphatic isocyanate | |
DE1081451B (en) | Process for the production of di- and polyisocyanates | |
ES432428A2 (en) | Organic polyisocyanates | |
GB1346402A (en) | Polyisocyanates and their use in the production of polyurethane plastics | |
Lowe | Isocyanates in Industry: The Chemistry of Isocyanates | |
JPS57158751A (en) | Manufacture of urethane and use as isocyanate manufacturing raw material | |
ATE80158T1 (en) | PROCESSES FOR THE PRODUCTION OF PRIMARY ARALKYLURETHANES, UREAS AND ISOCYANATES DERIVED FROM THEM. | |
GB1359428A (en) | Process for the preparation of organic sulphonylisocyanates | |
ES8207134A1 (en) | Process for the preparation of N,O-disubstituted urethanes, and their use as raw materials in the manufacture of isocyanates. | |
GB908949A (en) | Improvements in or relating to the manufacture of polymers | |
GB1146664A (en) | Process for the manufacture of organic isocyanates | |
US2675403A (en) | Carbamates containing the cycloheptatrien-1-ol-2-one ring | |
DE3788380D1 (en) | Process for the preparation of urethane and / or urea group-containing polyaminohydroxyl compounds and their use for the production of polyurea urethanes. | |
GB918396A (en) | Benzenesulphonyl ureas and process for their manufacture |