BE511677A - - Google Patents
Info
- Publication number
- BE511677A BE511677A BE511677DA BE511677A BE 511677 A BE511677 A BE 511677A BE 511677D A BE511677D A BE 511677DA BE 511677 A BE511677 A BE 511677A
- Authority
- BE
- Belgium
- Prior art keywords
- phenyl
- para
- bis
- thioureas
- formula
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 claims description 8
- 125000004432 carbon atoms Chemical group C* 0.000 claims description 6
- ZWZVWGITAAIFPS-UHFFFAOYSA-N Thiophosgene Chemical compound ClC(Cl)=S ZWZVWGITAAIFPS-UHFFFAOYSA-N 0.000 claims description 4
- 230000001034 aminogenic Effects 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- 150000003585 thioureas Chemical class 0.000 claims description 4
- QKFJKGMPGYROCL-UHFFFAOYSA-N Phenyl isothiocyanate Chemical compound S=C=NC1=CC=CC=C1 QKFJKGMPGYROCL-UHFFFAOYSA-N 0.000 claims description 2
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 238000000034 method Methods 0.000 claims description 2
- 238000002560 therapeutic procedure Methods 0.000 claims description 2
- ARSPSQDAZJLGOB-UHFFFAOYSA-N 1-(4-ethoxyphenyl)-3-[4-(2-methylpropoxy)phenyl]thiourea Chemical compound C1=CC(OCC)=CC=C1NC(=S)NC1=CC=C(OCC(C)C)C=C1 ARSPSQDAZJLGOB-UHFFFAOYSA-N 0.000 claims 1
- 210000000988 Bone and Bones Anatomy 0.000 claims 1
- DXHPZXWIPWDXHJ-UHFFFAOYSA-N Carbon monosulfide Chemical compound [S+]#[C-] DXHPZXWIPWDXHJ-UHFFFAOYSA-N 0.000 claims 1
- 150000001491 aromatic compounds Chemical class 0.000 claims 1
- 150000002430 hydrocarbons Chemical class 0.000 claims 1
- -1 iso-butoxy-phenyl Chemical group 0.000 claims 1
- 229940117953 phenylisothiocyanate Drugs 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 15
- HEDRZPFGACZZDS-UHFFFAOYSA-N chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- QGJOPFRUJISHPQ-UHFFFAOYSA-N carbon bisulphide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- DWOIGSLSPPLRKO-UHFFFAOYSA-N 4-propoxyaniline Chemical compound CCCOC1=CC=C(N)C=C1 DWOIGSLSPPLRKO-UHFFFAOYSA-N 0.000 description 4
- MHAJPDPJQMAIIY-UHFFFAOYSA-N hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 4
- 239000000155 melt Substances 0.000 description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 4
- 229910052717 sulfur Inorganic materials 0.000 description 4
- 239000011593 sulfur Substances 0.000 description 4
- JCBJVAJGLKENNC-UHFFFAOYSA-M Potassium ethyl xanthate Chemical compound [K+].CCOC([S-])=S JCBJVAJGLKENNC-UHFFFAOYSA-M 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- MKKOMLHZQBUJMH-UHFFFAOYSA-N 1,3-bis(4-propoxyphenyl)thiourea Chemical compound C1=CC(OCCC)=CC=C1NC(=S)NC1=CC=C(OCCC)C=C1 MKKOMLHZQBUJMH-UHFFFAOYSA-N 0.000 description 2
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 2
- UBRIHZOFEJHMIT-UHFFFAOYSA-N 4-butoxyaniline Chemical compound CCCCOC1=CC=C(N)C=C1 UBRIHZOFEJHMIT-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 229940079593 drugs Drugs 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- IXBVMHHGEKZUKE-UHFFFAOYSA-N 1,3-bis(4-butoxyphenyl)thiourea Chemical compound C1=CC(OCCCC)=CC=C1NC(=S)NC1=CC=C(OCCCC)C=C1 IXBVMHHGEKZUKE-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- SKHKUCUFZDEUTM-UHFFFAOYSA-N C1(=CC=C(C=C1)OCC)NC(=S)NC1=CC=C(C=C1)OCCC Chemical compound C1(=CC=C(C=C1)OCC)NC(=S)NC1=CC=C(C=C1)OCCC SKHKUCUFZDEUTM-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate dianion Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 150000001448 anilines Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 230000003197 catalytic Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 229940042396 direct acting antivirals Thiosemicarbazones Drugs 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxyl anion Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000003584 thiosemicarbazones Chemical class 0.000 description 1
- 201000008827 tuberculosis Diseases 0.000 description 1
Classifications
-
- 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
- C07C335/18—Derivatives of thiourea having nitrogen atoms of thiourea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton being further substituted by singly-bound oxygen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| BE511677A true BE511677A (xx) |
Family
ID=150369
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BE511677D BE511677A (xx) |
Country Status (1)
| Country | Link |
|---|---|
| BE (1) | BE511677A (xx) |
-
0
- BE BE511677D patent/BE511677A/fr unknown
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