PL73565B1 - - Google Patents
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- Publication number
- PL73565B1 PL73565B1 PL1971147631A PL14763171A PL73565B1 PL 73565 B1 PL73565 B1 PL 73565B1 PL 1971147631 A PL1971147631 A PL 1971147631A PL 14763171 A PL14763171 A PL 14763171A PL 73565 B1 PL73565 B1 PL 73565B1
- Authority
- PL
- Poland
- Prior art keywords
- dinitrophenyl
- chloro
- treated
- thiocyanate
- formula
- Prior art date
Links
- 238000000034 method Methods 0.000 claims description 25
- BLYYHVGDIRNVNY-UHFFFAOYSA-N (4-chloro-3,5-dinitrophenyl) thiocyanate Chemical compound [O-][N+](=O)C1=CC(SC#N)=CC([N+]([O-])=O)=C1Cl BLYYHVGDIRNVNY-UHFFFAOYSA-N 0.000 claims description 11
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 claims description 6
- 239000000908 ammonium hydroxide Substances 0.000 claims description 6
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 4
- 229910052700 potassium Inorganic materials 0.000 claims description 4
- 239000011591 potassium Substances 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 claims description 3
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims description 3
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 3
- IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 claims description 3
- 150000001412 amines Chemical class 0.000 claims description 3
- 229910052792 caesium Inorganic materials 0.000 claims description 3
- TVFDJXOCXUVLDH-UHFFFAOYSA-N caesium atom Chemical compound [Cs] TVFDJXOCXUVLDH-UHFFFAOYSA-N 0.000 claims description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 229910052708 sodium Inorganic materials 0.000 claims description 3
- 239000011734 sodium Substances 0.000 claims description 3
- XVMATWZWYNOQHG-UHFFFAOYSA-N 1-[(3,5-dinitrophenyl)disulfanyl]-3,5-dinitrobenzene Chemical class [O-][N+](=O)C1=CC([N+](=O)[O-])=CC(SSC=2C=C(C=C(C=2)[N+]([O-])=O)[N+]([O-])=O)=C1 XVMATWZWYNOQHG-UHFFFAOYSA-N 0.000 claims description 2
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims description 2
- 125000003342 alkenyl group Chemical group 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 229910052744 lithium Inorganic materials 0.000 claims description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 claims 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims 1
- WEHWNAOGRSTTBQ-UHFFFAOYSA-N dipropylamine Chemical compound CCCNCCC WEHWNAOGRSTTBQ-UHFFFAOYSA-N 0.000 claims 1
- QHCCDDQKNUYGNC-UHFFFAOYSA-N n-ethylbutan-1-amine Chemical compound CCCCNCC QHCCDDQKNUYGNC-UHFFFAOYSA-N 0.000 claims 1
- DYUWTXWIYMHBQS-UHFFFAOYSA-N n-prop-2-enylprop-2-en-1-amine Chemical compound C=CCNCC=C DYUWTXWIYMHBQS-UHFFFAOYSA-N 0.000 claims 1
- RGSODMOUXWISAG-UHFFFAOYSA-N n-prop-2-ynylprop-2-yn-1-amine Chemical compound C#CCNCC#C RGSODMOUXWISAG-UHFFFAOYSA-N 0.000 claims 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 claims 1
- 235000017557 sodium bicarbonate Nutrition 0.000 claims 1
- 239000000047 product Substances 0.000 description 13
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- -1 1-buten-2-yl Chemical group 0.000 description 9
- 150000001875 compounds Chemical class 0.000 description 9
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- 239000000203 mixture Substances 0.000 description 8
- BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical compound SS BWGNESOTFCXPMA-UHFFFAOYSA-N 0.000 description 7
- 230000002363 herbicidal effect Effects 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical group CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 4
- 229910021529 ammonia Inorganic materials 0.000 description 4
- 238000009833 condensation Methods 0.000 description 4
- 230000005494 condensation Effects 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- NSCBEXDNDMWCNW-UHFFFAOYSA-N 4-[(4-hydroxy-3,5-dinitrophenyl)disulfanyl]-2,6-dinitrophenol Chemical compound OC1=C(C=C(C=C1[N+](=O)[O-])SSC1=CC(=C(C(=C1)[N+](=O)[O-])O)[N+](=O)[O-])[N+](=O)[O-] NSCBEXDNDMWCNW-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
- 125000003277 amino group Chemical group 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- ALVPDCHBQRCKRQ-UHFFFAOYSA-N 4-chloro-3,5-dinitrobenzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC([N+]([O-])=O)=C(Cl)C([N+]([O-])=O)=C1 ALVPDCHBQRCKRQ-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N Methyl ethyl ketone Natural products CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- ZMZDMBWJUHKJPS-UHFFFAOYSA-M Thiocyanate anion Chemical compound [S-]C#N ZMZDMBWJUHKJPS-UHFFFAOYSA-M 0.000 description 2
- 238000000862 absorption spectrum Methods 0.000 description 2
- 150000001339 alkali metal compounds Chemical class 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 238000005660 chlorination reaction Methods 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 239000004009 herbicide Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- ZMZDMBWJUHKJPS-UHFFFAOYSA-N hydrogen thiocyanate Natural products SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 description 2
- 238000001819 mass spectrum Methods 0.000 description 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 2
- 150000005619 secondary aliphatic amines Chemical class 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- BFCFYVKQTRLZHA-UHFFFAOYSA-N 1-chloro-2-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1Cl BFCFYVKQTRLZHA-UHFFFAOYSA-N 0.000 description 1
- 125000000530 1-propynyl group Chemical group [H]C([H])([H])C#C* 0.000 description 1
- QIKCGZUCTWPNJM-UHFFFAOYSA-N 2-chloro-5-[(4-chloro-3,5-dinitrophenyl)disulfanyl]-1,3-dinitrobenzene Chemical compound [O-][N+](=O)C1=C(Cl)C([N+](=O)[O-])=CC(SSC=2C=C(C(Cl)=C(C=2)[N+]([O-])=O)[N+]([O-])=O)=C1 QIKCGZUCTWPNJM-UHFFFAOYSA-N 0.000 description 1
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 1
- GSTCLLCEBJUOLB-UHFFFAOYSA-N 3,5-dinitrobenzenesulfonyl chloride Chemical group [O-][N+](=O)C1=CC([N+]([O-])=O)=CC(S(Cl)(=O)=O)=C1 GSTCLLCEBJUOLB-UHFFFAOYSA-N 0.000 description 1
- CWQPCJBGDCRFRL-UHFFFAOYSA-N 3-butyl-6-[[4-butyl-2-(ethylamino)-3,5-dinitrophenyl]disulfanyl]-N-ethyl-2,4-dinitroaniline Chemical compound C(CCC)C1=C(C(=C(C=C1[N+](=O)[O-])SSC1=C(C(=C(C(=C1)[N+](=O)[O-])CCCC)[N+](=O)[O-])NCC)NCC)[N+](=O)[O-] CWQPCJBGDCRFRL-UHFFFAOYSA-N 0.000 description 1
- 125000000474 3-butynyl group Chemical group [H]C#CC([H])([H])C([H])([H])* 0.000 description 1
- KOJGJYRBTGJHHD-UHFFFAOYSA-N 4-[(4-amino-3,5-dinitrophenyl)disulfanyl]-2,6-dinitroaniline Chemical compound NC1=C(C=C(C=C1[N+](=O)[O-])SSC1=CC(=C(C(=C1)[N+](=O)[O-])N)[N+](=O)[O-])[N+](=O)[O-] KOJGJYRBTGJHHD-UHFFFAOYSA-N 0.000 description 1
- QPPCKCYMESOOPN-UHFFFAOYSA-N 4-amino-3,5-dinitrobenzenesulfonyl chloride Chemical compound NC1=C([N+]([O-])=O)C=C(S(Cl)(=O)=O)C=C1[N+]([O-])=O QPPCKCYMESOOPN-UHFFFAOYSA-N 0.000 description 1
- KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 description 1
- 244000025254 Cannabis sativa Species 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- 244000068988 Glycine max Species 0.000 description 1
- 235000010469 Glycine max Nutrition 0.000 description 1
- 241000219146 Gossypium Species 0.000 description 1
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 240000007594 Oryza sativa Species 0.000 description 1
- 235000007164 Oryza sativa Nutrition 0.000 description 1
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 1
- 240000008042 Zea mays Species 0.000 description 1
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 125000006323 alkenyl amino group Chemical group 0.000 description 1
- 125000003282 alkyl amino group Chemical group 0.000 description 1
- 125000006319 alkynyl amino group Chemical group 0.000 description 1
- 125000000304 alkynyl group Chemical group 0.000 description 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
- 125000003368 amide group Chemical group 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- CSKNSYBAZOQPLR-UHFFFAOYSA-N benzenesulfonyl chloride Chemical class ClS(=O)(=O)C1=CC=CC=C1 CSKNSYBAZOQPLR-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 235000005822 corn Nutrition 0.000 description 1
- 125000002228 disulfide group Chemical group 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 description 1
- 238000007040 multi-step synthesis reaction Methods 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000006396 nitration reaction Methods 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US3022870A | 1970-04-20 | 1970-04-20 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| PL73565B1 true PL73565B1 (forum.php) | 1974-10-30 |
Family
ID=21853188
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL1971147631A PL73565B1 (forum.php) | 1970-04-20 | 1971-04-19 |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US3725479A (forum.php) |
| JP (1) | JPS5529070B2 (forum.php) |
| AT (1) | AT308719B (forum.php) |
| CH (2) | CH554850A (forum.php) |
| HU (1) | HU163257B (forum.php) |
| IE (1) | IE35061B1 (forum.php) |
| IL (1) | IL36584A (forum.php) |
| NL (1) | NL7103904A (forum.php) |
| PL (1) | PL73565B1 (forum.php) |
| SE (1) | SE391334B (forum.php) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP3212899B1 (en) | 2014-10-27 | 2023-10-18 | Cummins Inc. | Waste heat recovery integrated cooling module |
| CN108495976B (zh) | 2015-12-21 | 2021-05-28 | 康明斯公司 | 废热回收动力驱动 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA462497A (en) * | 1950-01-17 | Timothy Paul Philip | Manufacture of dithio bis-arylamine | |
| NL132336C (forum.php) * | 1951-01-28 |
-
1970
- 1970-04-20 US US00030228A patent/US3725479A/en not_active Expired - Lifetime
-
1971
- 1971-03-23 NL NL7103904A patent/NL7103904A/xx not_active Application Discontinuation
- 1971-04-09 IL IL36584A patent/IL36584A/en unknown
- 1971-04-14 AT AT315471A patent/AT308719B/de not_active IP Right Cessation
- 1971-04-15 IE IE465/71A patent/IE35061B1/xx unknown
- 1971-04-16 SE SE7105001A patent/SE391334B/xx unknown
- 1971-04-19 HU HUEI376A patent/HU163257B/hu unknown
- 1971-04-19 CH CH565271A patent/CH554850A/xx not_active IP Right Cessation
- 1971-04-19 CH CH1525473A patent/CH575389A5/xx not_active IP Right Cessation
- 1971-04-19 PL PL1971147631A patent/PL73565B1/pl unknown
- 1971-04-19 JP JP2460871A patent/JPS5529070B2/ja not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| CH554850A (de) | 1974-10-15 |
| NL7103904A (forum.php) | 1971-10-22 |
| SE391334B (sv) | 1977-02-14 |
| HU163257B (forum.php) | 1973-07-28 |
| IE35061B1 (en) | 1975-10-29 |
| IL36584A0 (en) | 1971-06-23 |
| JPS5529070B2 (forum.php) | 1980-07-31 |
| JPS465071A (forum.php) | 1971-11-24 |
| AT308719B (de) | 1973-07-25 |
| IE35061L (en) | 1971-10-20 |
| US3725479A (en) | 1973-04-03 |
| IL36584A (en) | 1974-11-29 |
| CH575389A5 (forum.php) | 1976-05-14 |
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