BE497785A - - Google Patents
Info
- Publication number
- BE497785A BE497785A BE497785DA BE497785A BE 497785 A BE497785 A BE 497785A BE 497785D A BE497785D A BE 497785DA BE 497785 A BE497785 A BE 497785A
- Authority
- BE
- Belgium
- Prior art keywords
- sep
- thiouracil
- methylbenzyl
- methylphenylacetylacetate
- ethyl
- Prior art date
Links
- -1 ethyl m-methylphenylacetylacetate Chemical compound 0.000 claims description 14
- ZEMGGZBWXRYJHK-UHFFFAOYSA-N Thiouracil Chemical class O=C1C=CNC(=S)N1 ZEMGGZBWXRYJHK-UHFFFAOYSA-N 0.000 claims description 9
- KQJQICVXLJTWQD-UHFFFAOYSA-N N-methylthiourea Chemical compound CNC(N)=S KQJQICVXLJTWQD-UHFFFAOYSA-N 0.000 claims description 4
- UMGDCJDMYOKAJW-UHFFFAOYSA-N Thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- GDXNSFVXXGAUMU-UHFFFAOYSA-N ethyl 4-(4-methylphenyl)-3-oxobutanoate Chemical compound CCOC(=O)CC(=O)CC1=CC=C(C)C=C1 GDXNSFVXXGAUMU-UHFFFAOYSA-N 0.000 claims description 3
- 238000000034 method Methods 0.000 claims description 3
- KHWQJTTWERTQIS-UHFFFAOYSA-N 6-[(3-methylphenyl)methyl]-2-sulfanylidene-1H-pyrimidin-4-one Chemical compound CC1=CC=CC(CC=2NC(=S)NC(=O)C=2)=C1 KHWQJTTWERTQIS-UHFFFAOYSA-N 0.000 claims description 2
- 150000002148 esters Chemical class 0.000 claims description 2
- GAFBGRBPYCNUCH-UHFFFAOYSA-N 4-Methylbenzyl radical Chemical group [CH2]C1=CC=C(C)C=C1 GAFBGRBPYCNUCH-UHFFFAOYSA-N 0.000 claims 1
- 229920001098 polystyrene-block-poly(ethylene/propylene) Polymers 0.000 description 27
- 229910052757 nitrogen Inorganic materials 0.000 description 9
- 229910052717 sulfur Inorganic materials 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- 230000000694 effects Effects 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- 239000011777 magnesium Substances 0.000 description 4
- 230000001988 toxicity Effects 0.000 description 4
- 231100000419 toxicity Toxicity 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- FYYHWMGAXLPEAU-UHFFFAOYSA-N magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 3
- 229910052749 magnesium Inorganic materials 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- LTMRRSWNXVJMBA-UHFFFAOYSA-L 2,2-diethylpropanedioate Chemical compound CCC(CC)(C([O-])=O)C([O-])=O LTMRRSWNXVJMBA-UHFFFAOYSA-L 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N Carbon tetrachloride Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N Thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 230000000875 corresponding Effects 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L na2so4 Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- BGGKEDDFKBVTDK-UHFFFAOYSA-N 2-(3-methylphenyl)acetyl chloride Chemical compound CC1=CC=CC(CC(Cl)=O)=C1 BGGKEDDFKBVTDK-UHFFFAOYSA-N 0.000 description 1
- NKGFCNNAZAKQTQ-UHFFFAOYSA-N 6-(3-methoxyphenyl)-2-sulfanylidene-1H-pyrimidin-4-one Chemical compound COC1=CC=CC(C=2NC(=S)NC(=O)C=2)=C1 NKGFCNNAZAKQTQ-UHFFFAOYSA-N 0.000 description 1
- AATNPSPOECSJBO-UHFFFAOYSA-N 6-(4-methoxyphenyl)-2-sulfanylidene-1H-pyrimidin-4-one Chemical compound C1=CC(OC)=CC=C1C1=CC(=O)NC(=S)N1 AATNPSPOECSJBO-UHFFFAOYSA-N 0.000 description 1
- UPBWGKSZFHAGPE-UHFFFAOYSA-N 6-[(4-methylphenyl)methyl]-2-sulfanylidene-1H-pyrimidin-4-one Chemical compound C1=CC(C)=CC=C1CC1=CC(=O)NC(=S)N1 UPBWGKSZFHAGPE-UHFFFAOYSA-N 0.000 description 1
- PNXBXCRWXNESOV-UHFFFAOYSA-N 6-benzyl-2-sulfanylidene-1H-pyrimidin-4-one Chemical compound N1C(=S)NC(=O)C=C1CC1=CC=CC=C1 PNXBXCRWXNESOV-UHFFFAOYSA-N 0.000 description 1
- XEKNACRTWJHOCE-UHFFFAOYSA-N 6-phenyl-2-sulfanylidene-1H-pyrimidin-4-one Chemical compound O=C1NC(S)=NC(C=2C=CC=CC=2)=C1 XEKNACRTWJHOCE-UHFFFAOYSA-N 0.000 description 1
- RAIPHJJURHTUIC-UHFFFAOYSA-N Aminothiazole Chemical compound NC1=NC=CS1 RAIPHJJURHTUIC-UHFFFAOYSA-N 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N Sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 241000906446 Theraps Species 0.000 description 1
- 229940036565 Thiouracil antithyroid preparations Drugs 0.000 description 1
- 210000001685 Thyroid Gland Anatomy 0.000 description 1
- 230000003208 anti-thyroid Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 235000021185 dessert Nutrition 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000004435 hydrogen atoms Chemical group [H]* 0.000 description 1
- 125000006178 methyl benzyl group Chemical group 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- KVBGVZZKJNLNJU-UHFFFAOYSA-N naphthalene-2-sulfonic acid Chemical compound C1=CC=CC2=CC(S(=O)(=O)O)=CC=C21 KVBGVZZKJNLNJU-UHFFFAOYSA-N 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 230000001225 therapeutic Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/56—One oxygen atom and one sulfur atom
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| BE497785A true BE497785A (ko) |
Family
ID=140655
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BE497785D BE497785A (ko) |
Country Status (1)
| Country | Link |
|---|---|
| BE (1) | BE497785A (ko) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0354179A1 (de) * | 1988-07-29 | 1990-02-07 | Ciba-Geigy Ag | Thiouracile als Stabilisatoren für chlorhaltige Polymerisate |
-
0
- BE BE497785D patent/BE497785A/fr unknown
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0354179A1 (de) * | 1988-07-29 | 1990-02-07 | Ciba-Geigy Ag | Thiouracile als Stabilisatoren für chlorhaltige Polymerisate |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EP0073161B1 (fr) | Nouveaux dérivés de la pyrazine actifs sur le système nerveux central | |
| CH631151A5 (fr) | Procede de preparation d'hemiacetal-esters de l'acide glyoxylique. | |
| FR2572070A1 (fr) | Derives de la chalcone utiles en therapeutique | |
| CA1060039A (fr) | Derives des acides 3-benzoyl-phenylalcanoiques et-alcenoiques | |
| BE497785A (ko) | ||
| CA1178599A (fr) | Composes sulfures comportant un cycle lactonique, leur preparation et leur application a la preparation de derives cyclopropaniques | |
| EP0297987A1 (fr) | Procédé de préparation de l'acide (pyridyl-3)-3 1H,3H-pyrrolo [1,2-c] thiazolecarboxylique-7 dextrogyre | |
| CH392483A (fr) | Procédé de préparation de nouveaux esters d'acides 4-halo-3-sulfamoyl-benzoïques | |
| FR2583419A1 (fr) | Procede pour la preparation de 2-bromo-a-ergocryptine et ses sels d'addition d'acides. | |
| CA1100527A (fr) | Derives de l'acide cyclohexyl-4 naphtalene acetique-1, procede d'obtention et application a titre de medicament | |
| EP0007843A1 (fr) | Dérivés de propiophénone, leur application en thérapeutique et leur préparation | |
| BE451560A (fr) | Chlororcarbonates d'acoyles beta-halogenes et procede de preparation de ces produits | |
| BE491159A (ko) | ||
| CH371798A (fr) | Procédé de préparation de nouveaux esters de pipéridyl-2 phénylcarbinol | |
| BE551672A (ko) | ||
| BE633582A (ko) | ||
| FR2528834A1 (fr) | Sels d'ammonium quaternaires d'amines cycliques disubstituees en a et a' par des groupes phenylcarbamoyle eventuellement substitues sur le phenyl, et medicaments a action antiarythmique comportant lesdits sels | |
| CH314548A (fr) | Procédé de préparation d'un 1-p-nitrophényl-2-acylamido-propanediol-1,3 | |
| BE512973A (ko) | ||
| BE520959A (ko) | ||
| CH396031A (fr) | Procédé de préparation de nouveaux dérivés hydraziniques | |
| BE634833A (ko) | ||
| BE438574A (ko) | ||
| BE542106A (ko) | ||
| CH440315A (fr) | Procédé de fabrication d'hydrazides N2-substitués inhibiteurs de la mono-amine-oxydase |