GB854956A - Aromatic sulphonyl amino compounds containing trifluoromethyl radicals - Google Patents
Aromatic sulphonyl amino compounds containing trifluoromethyl radicalsInfo
- Publication number
- GB854956A GB854956A GB3671557A GB3671557A GB854956A GB 854956 A GB854956 A GB 854956A GB 3671557 A GB3671557 A GB 3671557A GB 3671557 A GB3671557 A GB 3671557A GB 854956 A GB854956 A GB 854956A
- Authority
- GB
- United Kingdom
- Prior art keywords
- trifluoromethyl
- chloromethane
- chloro
- compounds
- sulphochloride
- 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
- -1 Aromatic sulphonyl amino compounds Chemical class 0.000 title abstract 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 abstract 6
- GEKOHRZGXRUJIN-UHFFFAOYSA-N chloromethane;sulfurochloridic acid Chemical compound ClC.OS(Cl)(=O)=O GEKOHRZGXRUJIN-UHFFFAOYSA-N 0.000 abstract 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 abstract 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 abstract 2
- 238000005660 chlorination reaction Methods 0.000 abstract 2
- 229910052801 chlorine Inorganic materials 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- QLRBNEZOQPLERN-UHFFFAOYSA-N (sulfonylamino)benzene Chemical compound O=S(=O)=NC1=CC=CC=C1 QLRBNEZOQPLERN-UHFFFAOYSA-N 0.000 abstract 1
- TZGFQIXRVUHDLE-UHFFFAOYSA-N 1-chloro-2-nitro-4-(trifluoromethyl)benzene Chemical compound [O-][N+](=O)C1=CC(C(F)(F)F)=CC=C1Cl TZGFQIXRVUHDLE-UHFFFAOYSA-N 0.000 abstract 1
- HSQFVBWFPBKHEB-UHFFFAOYSA-N 2,3,4-trichlorophenol Chemical compound OC1=CC=C(Cl)C(Cl)=C1Cl HSQFVBWFPBKHEB-UHFFFAOYSA-N 0.000 abstract 1
- JARIALSGFXECCH-UHFFFAOYSA-N 2,4,5-trichlorobenzenethiol Chemical compound SC1=CC(Cl)=C(Cl)C=C1Cl JARIALSGFXECCH-UHFFFAOYSA-N 0.000 abstract 1
- LHJGJYXLEPZJPM-UHFFFAOYSA-N 2,4,5-trichlorophenol Chemical compound OC1=CC(Cl)=C(Cl)C=C1Cl LHJGJYXLEPZJPM-UHFFFAOYSA-N 0.000 abstract 1
- DRKWGMXFFCPZLW-UHFFFAOYSA-N 2-fluoro-5-(trifluoromethyl)aniline Chemical compound NC1=CC(C(F)(F)F)=CC=C1F DRKWGMXFFCPZLW-UHFFFAOYSA-N 0.000 abstract 1
- 241000894006 Bacteria Species 0.000 abstract 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 abstract 1
- 241000233866 Fungi Species 0.000 abstract 1
- 229910021578 Iron(III) chloride Inorganic materials 0.000 abstract 1
- ATTZFSUZZUNHBP-UHFFFAOYSA-N Piperonyl sulfoxide Chemical compound CCCCCCCCS(=O)C(C)CC1=CC=C2OCOC2=C1 ATTZFSUZZUNHBP-UHFFFAOYSA-N 0.000 abstract 1
- 241000607479 Yersinia pestis Species 0.000 abstract 1
- 229960000583 acetic acid Drugs 0.000 abstract 1
- 150000001412 amines Chemical class 0.000 abstract 1
- 150000004982 aromatic amines Chemical class 0.000 abstract 1
- 239000004305 biphenyl Substances 0.000 abstract 1
- 235000010290 biphenyl Nutrition 0.000 abstract 1
- 125000006267 biphenyl group Chemical group 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- 239000000460 chlorine Substances 0.000 abstract 1
- 125000001309 chloro group Chemical group Cl* 0.000 abstract 1
- 125000004965 chloroalkyl group Chemical group 0.000 abstract 1
- 125000006421 chlorocycloalkyl group Chemical group 0.000 abstract 1
- URCLXLVQHAJFSJ-UHFFFAOYSA-N chlorosulfonyl hypochlorite Chemical class ClOS(Cl)(=O)=O URCLXLVQHAJFSJ-UHFFFAOYSA-N 0.000 abstract 1
- 238000009833 condensation Methods 0.000 abstract 1
- 230000005494 condensation Effects 0.000 abstract 1
- 239000007859 condensation product Substances 0.000 abstract 1
- 239000012362 glacial acetic acid Substances 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 abstract 1
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 abstract 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 abstract 1
- 239000002244 precipitate Substances 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 abstract 1
- 239000000047 product Substances 0.000 abstract 1
- 239000003223 protective agent Substances 0.000 abstract 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 abstract 1
- 150000003254 radicals Chemical class 0.000 abstract 1
- 125000001174 sulfone group Chemical group 0.000 abstract 1
- 239000004753 textile Substances 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- 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
- C09B43/12—Preparation of azo dyes from other azo compounds by acylation of amino groups
- C09B43/124—Preparation of azo dyes from other azo compounds by acylation of amino groups with monocarboxylic acids, carbamic esters or halides, mono- isocyanates, or haloformic acid esters
- C09B43/1247—Preparation of azo dyes from other azo compounds by acylation of amino groups with monocarboxylic acids, carbamic esters or halides, mono- isocyanates, or haloformic acid esters with formation of NHSO2R or NHSO3H radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/15—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
The invention comprises aromatic sulphonylamino compounds containing the trifluoromethyl radical-CF3 and having the general formulae: <FORM:0854956/IV(b)/1> wherein X stands for hydrogen, chlorine or the trifluoromethyl radical-CF3, at least one X being CF3, R stands for a chloroalkyl-, chlorocycloalkyl-, chloroaryl-, or chloroaralkyl radical, and Y stands for a diphenyl linkage or for O, S, SO, SO2, or CH2. The compounds are obtained by reacting monoof bi-nuclear aromatic amines, substituted in a nucleus with CF3, with the appropriate chloro-sulphochlorides followed, if desired, by direct chlorination. The compounds are effective protective agents against textile pests, fungi, and bacteria (see Group VIII). In Example 1, a pyridine solution of 41-chloro-4-trifluoromethyl-2-amino-1,11-diphenyl ether is treated at 0 DEG C. with chloromethane-sulphochloride. After standing for 12 hours at room temperature, the solution is poured into water whereby a precipitate comprising 41chloro-4-trifluoromethyl-2-chloromethane-sulphonylamino-1, 11-diphenyl ether is obtained. In Example 2, the product of Example 1 is dissolved in glacial acetic acid, and subjected to direct chlorination using ferric chloride as catalyst, whereby another chlorine atom is introduced into the molecule. Example 5 describes the condensation of 2, 4, 5-trichlorophenol with 3-nitro-4-chloro-benzotrifluoride, the reduction of the nitro condensation product to the corresponding amine, and the reaction of the latter with chloromethane-sulphochloride to yield 4-trifluoromethyl-2-chloromethane-sulphonamino-21, 41, 51trichloro-1, 11-diphenyl ether. When 2, 4, 5-trichlorothiophenol is employed in place of the trichlorophenol there is obtained 4-trifluoromethyl-2-chloromethane-sulphonylamino-21, 41, 51-trichloro-1, 11-diphenylsulphide, and this may be oxidized to the corresponding sulphoxide or sulphone. In Example 9, chloromethane sulphochloride is reacted with 2-fluoro-5-trifluoromethyl aniline to yield 2-fluoro-5-trifluoromethyl-1-chloromethane sulphonylaminobenzene. This example also refers to the preparation of 2-chloro-5-trifluoromethyl-41-chlorophenylsulphonyl -aminobenzene; also the corresponding 31, 41-dichloro-and 21, 41, 51 trichloro-compounds. Specifications 702,602, 709,455 and 738,758 are referred to.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF21888A DE1058049B (en) | 1956-12-08 | 1956-12-08 | Process for the production of protective agents against textile pests, mold and bacterial attack |
| DEF22658A DE1062238B (en) | 1957-03-23 | 1957-03-23 | Process for the production of protective agents against textile pests, mold and bacterial attack |
| DEF0026477 | 1958-08-23 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB854956A true GB854956A (en) | 1960-11-23 |
Family
ID=27210052
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB3671557A Expired GB854956A (en) | 1956-12-08 | 1957-11-25 | Aromatic sulphonyl amino compounds containing trifluoromethyl radicals |
| GB2623459A Expired GB900111A (en) | 1956-12-08 | 1959-07-30 | Trifluoromethyl-aryl-sulphonamides for use as protective agents against textile pests and as herbicides |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB2623459A Expired GB900111A (en) | 1956-12-08 | 1959-07-30 | Trifluoromethyl-aryl-sulphonamides for use as protective agents against textile pests and as herbicides |
Country Status (4)
| Country | Link |
|---|---|
| CH (2) | CH366038A (en) |
| DE (1) | DE1418197A1 (en) |
| GB (2) | GB854956A (en) |
| SE (1) | SE303127B (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3239564A (en) * | 1960-12-02 | 1966-03-08 | Reeder Earl | 2 n-substituted amino halobenzo-phenones |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL301745A (en) * | 1962-12-17 | |||
| US3953492A (en) * | 1975-03-27 | 1976-04-27 | Merck & Co., Inc. | Anthelmintic substituted sulfonamide derivatives |
| US3953493A (en) * | 1975-03-27 | 1976-04-27 | Merck & Co., Inc. | Substituted sulfonamide derivatives as anthelmintic agents |
-
1957
- 1957-10-30 CH CH5211357A patent/CH366038A/en unknown
- 1957-11-25 GB GB3671557A patent/GB854956A/en not_active Expired
-
1958
- 1958-08-23 DE DE19581418197 patent/DE1418197A1/en active Pending
-
1959
- 1959-06-29 CH CH7506959A patent/CH388297A/en unknown
- 1959-07-30 GB GB2623459A patent/GB900111A/en not_active Expired
- 1959-08-20 SE SE774659A patent/SE303127B/xx unknown
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3239564A (en) * | 1960-12-02 | 1966-03-08 | Reeder Earl | 2 n-substituted amino halobenzo-phenones |
Also Published As
| Publication number | Publication date |
|---|---|
| GB900111A (en) | 1962-07-04 |
| DE1418197A1 (en) | 1968-10-17 |
| CH388297A (en) | 1965-02-28 |
| CH366038A (en) | 1962-12-15 |
| SE303127B (en) | 1968-08-19 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US2703332A (en) | Poly halo-salicylanilioes | |
| US2745874A (en) | Insecticidal derivatives of diphenyl urea | |
| US3162684A (en) | New aminobenzoic acid deriatives and compositions containing same | |
| US4349681A (en) | 2-Amino-3-chloro-5-trifluoromethylpyridine | |
| GB854956A (en) | Aromatic sulphonyl amino compounds containing trifluoromethyl radicals | |
| US3198793A (en) | 6-dibenzo(c,e)-o-thiazine-5-dioxide and processes for their production | |
| NO137007B (en) | PROCEDURES FOR THE MANUFACTURE OF SULFUR DIOXIDE AND FACILITIES FOR IMPLEMENTING PROCEDURES | |
| US4006186A (en) | Process for the preparation of thiophenols | |
| US1932595A (en) | Halogenated bis-(hydroxy-aryl)-oxides | |
| GB876526A (en) | Process for the production of new aminobenzoic acid derivatives and their use in pest control | |
| US3156704A (en) | Arylcyanomethylene quinone oximes and their derivatives | |
| GB856452A (en) | Protective agents against textile pests, mould and bacteria | |
| US3904696A (en) | Halogenated hydroxy-diphenyl ethers | |
| Van Daalen et al. | The chemistry, herbicidal and fungicidal activities of 2, 1, 3‐benzothiadiazoles | |
| Doak | A modified Bart reaction | |
| JPS62298562A (en) | Production of bromoaniline or such | |
| Cromwell et al. | α-Chloro-β-amino Ketones | |
| GB731495A (en) | Heterocyclic ether-sulphones | |
| Cremlyn et al. | Some Phenoxybenzenesulfonyl Chlorides and Related Compounds | |
| DE1909520B2 (en) | METHOD FOR MANUFACTURING AROMATIC DIAMINES | |
| US1922240A (en) | Di-phenyl phenolphthalein, substitution products thereof, and method of preparing same | |
| Mahapatra | Synthesis of isomeric bromothiazolylamines and the use of their mercurated derivatives as fungicides and bactericides | |
| DE1273534B (en) | Process for the preparation of diaryl ether sultams | |
| AT209894B (en) | Process for the production of new anthranilic acid derivatives | |
| JPS59231064A (en) | Preparation of 2-mercaptoethylamine compound |