DE2608094B1 - Verfahren zur herstellung von phenyl-jodoniumchloridverbindungen - Google Patents
Verfahren zur herstellung von phenyl-jodoniumchloridverbindungenInfo
- Publication number
- DE2608094B1 DE2608094B1 DE19762608094 DE2608094A DE2608094B1 DE 2608094 B1 DE2608094 B1 DE 2608094B1 DE 19762608094 DE19762608094 DE 19762608094 DE 2608094 A DE2608094 A DE 2608094A DE 2608094 B1 DE2608094 B1 DE 2608094B1
- Authority
- DE
- Germany
- Prior art keywords
- general formula
- benzene
- compound
- thiophene
- stage
- 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.)
- Granted
Links
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical class I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 title claims abstract 3
- -1 tri-chloroacetoxy Chemical group 0.000 title claims description 3
- 150000008424 iodobenzenes Chemical class 0.000 title abstract 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims abstract description 34
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims abstract description 24
- 229930192474 thiophene Natural products 0.000 claims abstract description 12
- 238000006243 chemical reaction Methods 0.000 claims abstract description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 4
- 238000000034 method Methods 0.000 claims description 13
- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 claims description 9
- 150000001875 compounds Chemical class 0.000 claims description 7
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims 5
- VRGOGZVVYICPLH-UHFFFAOYSA-N iodobenzene;hydrochloride Chemical class Cl.IC1=CC=CC=C1 VRGOGZVVYICPLH-UHFFFAOYSA-N 0.000 claims 4
- 238000002360 preparation method Methods 0.000 claims 4
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims 2
- 241000221785 Erysiphales Species 0.000 claims 2
- WDKIYIMDQUIFFI-UHFFFAOYSA-N O=C(C(Cl)(Cl)Cl)OC(C=CC=C1)=C1I Chemical class O=C(C(Cl)(Cl)Cl)OC(C=CC=C1)=C1I WDKIYIMDQUIFFI-UHFFFAOYSA-N 0.000 claims 2
- 150000005224 alkoxybenzenes Chemical class 0.000 claims 2
- 239000003973 paint Substances 0.000 claims 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 2
- 150000003839 salts Chemical class 0.000 claims 2
- KTOOMIYOUDGYCE-UHFFFAOYSA-N C1=CC=CC=C1.C(C)(=O)OIOC(C)=O Chemical class C1=CC=CC=C1.C(C)(=O)OIOC(C)=O KTOOMIYOUDGYCE-UHFFFAOYSA-N 0.000 claims 1
- 241000233866 Fungi Species 0.000 claims 1
- 239000000853 adhesive Substances 0.000 claims 1
- 230000001070 adhesive effect Effects 0.000 claims 1
- 150000004996 alkyl benzenes Chemical class 0.000 claims 1
- 239000004599 antimicrobial Substances 0.000 claims 1
- 230000001580 bacterial effect Effects 0.000 claims 1
- 150000001805 chlorine compounds Chemical class 0.000 claims 1
- 239000000498 cooling water Substances 0.000 claims 1
- 239000003599 detergent Substances 0.000 claims 1
- 229910052602 gypsum Inorganic materials 0.000 claims 1
- 239000010440 gypsum Substances 0.000 claims 1
- 238000011065 in-situ storage Methods 0.000 claims 1
- PCRAJOWHMTYSKR-UHFFFAOYSA-N iodobenzene;2,2,2-trifluoroacetic acid Chemical class OC(=O)C(F)(F)F.IC1=CC=CC=C1 PCRAJOWHMTYSKR-UHFFFAOYSA-N 0.000 claims 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
- 230000003641 microbiacidal effect Effects 0.000 claims 1
- 239000004570 mortar (masonry) Substances 0.000 claims 1
- 239000011347 resin Substances 0.000 claims 1
- 229920005989 resin Polymers 0.000 claims 1
- 239000002453 shampoo Substances 0.000 claims 1
- 239000000344 soap Substances 0.000 claims 1
- 241000894007 species Species 0.000 claims 1
- 239000002023 wood Substances 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 abstract 3
- 125000003545 alkoxy group Chemical group 0.000 abstract 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 2
- JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical compound O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 abstract 1
- 241000607142 Salmonella Species 0.000 abstract 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 abstract 1
- 230000000845 anti-microbial effect Effects 0.000 abstract 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 abstract 1
- 239000000543 intermediate Substances 0.000 abstract 1
- 239000006916 nutrient agar Substances 0.000 abstract 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 abstract 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 24
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 14
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 11
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
- 239000002904 solvent Substances 0.000 description 8
- 239000000047 product Substances 0.000 description 7
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- JXTHNDFMNIQAHM-UHFFFAOYSA-N dichloroacetic acid Chemical class OC(=O)C(Cl)Cl JXTHNDFMNIQAHM-UHFFFAOYSA-N 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- MUDNTMPKEQHPDK-UHFFFAOYSA-M (4-chlorophenyl)-thiophen-2-yliodanium;chloride Chemical compound [Cl-].C1=CC(Cl)=CC=C1[I+]C1=CC=CS1 MUDNTMPKEQHPDK-UHFFFAOYSA-M 0.000 description 3
- 150000003841 chloride salts Chemical class 0.000 description 3
- 239000000155 melt Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- NUTRTWQRDYLPFF-UHFFFAOYSA-N 1-chloro-4-iodosylbenzene Chemical compound ClC1=CC=C(I=O)C=C1 NUTRTWQRDYLPFF-UHFFFAOYSA-N 0.000 description 2
- 150000001555 benzenes Chemical class 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 239000000470 constituent Substances 0.000 description 2
- 229960005215 dichloroacetic acid Drugs 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- FIQRKNHBJMJBQW-UHFFFAOYSA-M (4-chlorophenyl)-thiophen-2-yliodanium;2,2,2-trichloroacetate Chemical compound [O-]C(=O)C(Cl)(Cl)Cl.C1=CC(Cl)=CC=C1[I+]C1=CC=CS1 FIQRKNHBJMJBQW-UHFFFAOYSA-M 0.000 description 1
- NUATZKRRNUPSDW-UHFFFAOYSA-M (4-chlorophenyl)-thiophen-2-yliodanium;2,2-dichloroacetate Chemical compound [O-]C(=O)C(Cl)Cl.C1=CC(Cl)=CC=C1[I+]C1=CC=CS1 NUATZKRRNUPSDW-UHFFFAOYSA-M 0.000 description 1
- UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 1
- CYTYCFOTNPOANT-UHFFFAOYSA-N Perchloroethylene Chemical group ClC(Cl)=C(Cl)Cl CYTYCFOTNPOANT-UHFFFAOYSA-N 0.000 description 1
- IGYRZJCFGWQCIG-UHFFFAOYSA-N [6-chloro-2-(2,2-dichloroacetyl)oxy-3-iodophenyl] 2,2-dichloroacetate Chemical compound ClC(Cl)C(=O)OC1=C(Cl)C=CC(I)=C1OC(=O)C(Cl)Cl IGYRZJCFGWQCIG-UHFFFAOYSA-N 0.000 description 1
- UDTCRXPGZSHHBM-UHFFFAOYSA-N [6-chloro-3-iodo-2-(2,2,2-trichloroacetyl)oxyphenyl] 2,2,2-trichloroacetate Chemical compound ClC1=CC=C(I)C(OC(=O)C(Cl)(Cl)Cl)=C1OC(=O)C(Cl)(Cl)Cl UDTCRXPGZSHHBM-UHFFFAOYSA-N 0.000 description 1
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- IMNFDUFMRHMDMM-UHFFFAOYSA-N anhydrous n-heptane Natural products CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical class OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- 150000001721 carbon Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000012454 non-polar solvent Substances 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 238000006748 scratching Methods 0.000 description 1
- 230000002393 scratching effect Effects 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 229950011008 tetrachloroethylene Drugs 0.000 description 1
- 229940066528 trichloroacetate Drugs 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom 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
- C07D333/28—Halogen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19762608094 DE2608094B1 (de) | 1976-02-27 | 1976-02-27 | Verfahren zur herstellung von phenyl-jodoniumchloridverbindungen |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19762608094 DE2608094B1 (de) | 1976-02-27 | 1976-02-27 | Verfahren zur herstellung von phenyl-jodoniumchloridverbindungen |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2608094B1 true DE2608094B1 (de) | 1977-08-04 |
| DE2608094C2 DE2608094C2 (enrdf_load_stackoverflow) | 1978-04-06 |
Family
ID=5971092
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19762608094 Granted DE2608094B1 (de) | 1976-02-27 | 1976-02-27 | Verfahren zur herstellung von phenyl-jodoniumchloridverbindungen |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE2608094B1 (enrdf_load_stackoverflow) |
-
1976
- 1976-02-27 DE DE19762608094 patent/DE2608094B1/de active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| DE2608094C2 (enrdf_load_stackoverflow) | 1978-04-06 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EHJ | Ceased/non-payment of the annual fee |