BE637472A - - Google Patents
Info
- Publication number
- BE637472A BE637472A BE637472DA BE637472A BE 637472 A BE637472 A BE 637472A BE 637472D A BE637472D A BE 637472DA BE 637472 A BE637472 A BE 637472A
- Authority
- BE
- Belgium
- Prior art keywords
- benzanilide
- general formula
- radical
- thiophosgene
- amino
- Prior art date
Links
- ZWZVWGITAAIFPS-UHFFFAOYSA-N Thiophosgene Chemical compound ClC(Cl)=S ZWZVWGITAAIFPS-UHFFFAOYSA-N 0.000 claims description 12
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 125000004435 hydrogen atoms Chemical group [H]* 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- 125000001424 substituent group Chemical group 0.000 claims description 4
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 3
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- MDFFNEOEWAXZRQ-UHFFFAOYSA-N Amino radical Chemical compound [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 claims description 2
- 230000000507 anthelmentic Effects 0.000 claims description 2
- JXHYCCGOZUGBFD-UHFFFAOYSA-M benzoic acid;chloride Chemical compound [Cl-].OC(=O)C1=CC=CC=C1 JXHYCCGOZUGBFD-UHFFFAOYSA-M 0.000 claims description 2
- 239000000203 mixture Substances 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- 230000000875 corresponding Effects 0.000 claims 1
- ZVSKZLHKADLHSD-UHFFFAOYSA-N Benzanilide Chemical class C=1C=CC=CC=1C(=O)NC1=CC=CC=C1 ZVSKZLHKADLHSD-UHFFFAOYSA-N 0.000 description 9
- 238000002844 melting Methods 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- YMWUJEATGCHHMB-UHFFFAOYSA-N methylene dichloride Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 8
- VTYYLEPIZMXCLO-UHFFFAOYSA-L calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N acetic acid ethyl ester Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- KPSPULPPMWHXGE-UHFFFAOYSA-N 3-amino-N-phenylbenzamide Chemical compound NC1=CC=CC(C(=O)NC=2C=CC=CC=2)=C1 KPSPULPPMWHXGE-UHFFFAOYSA-N 0.000 description 2
- 229960003563 Calcium Carbonate Drugs 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate dianion Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 2
- 229910000019 calcium carbonate Inorganic materials 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000005712 crystallization Effects 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 2
- 229910052753 mercury Inorganic materials 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- ZMANZCXQSJIPKH-UHFFFAOYSA-N triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 2
- ICSNLGPSRYBMBD-UHFFFAOYSA-N 2-Aminopyridine Chemical compound NC1=CC=CC=N1 ICSNLGPSRYBMBD-UHFFFAOYSA-N 0.000 description 1
- MBBQXNUGYYNUAZ-UHFFFAOYSA-N 2-chloro-4-nitro-N-(4-nitrophenyl)benzamide Chemical compound C1=CC([N+](=O)[O-])=CC=C1NC(=O)C1=CC=C([N+]([O-])=O)C=C1Cl MBBQXNUGYYNUAZ-UHFFFAOYSA-N 0.000 description 1
- OMIOAPDWNQGXED-UHFFFAOYSA-N 3-amino-N-(3-aminophenyl)benzamide Chemical compound NC1=CC=CC(NC(=O)C=2C=C(N)C=CC=2)=C1 OMIOAPDWNQGXED-UHFFFAOYSA-N 0.000 description 1
- JUICYXZGXSVGOH-UHFFFAOYSA-N 3-isothiocyanato-N-(4-isothiocyanatophenyl)benzamide Chemical compound C=1C=CC(N=C=S)=CC=1C(=O)NC1=CC=C(N=C=S)C=C1 JUICYXZGXSVGOH-UHFFFAOYSA-N 0.000 description 1
- -1 4'-hydroxyisothiocyanato-benzanilide Chemical compound 0.000 description 1
- QFWZVUKQCBTKID-UHFFFAOYSA-N 4-amino-N-(4-amino-2-chlorophenyl)benzamide Chemical compound C1=CC(N)=CC=C1C(=O)NC1=CC=C(N)C=C1Cl QFWZVUKQCBTKID-UHFFFAOYSA-N 0.000 description 1
- UNLDYLKYVUHALD-UHFFFAOYSA-N 4-amino-N-(4-aminophenyl)-2-chlorobenzamide Chemical compound C1=CC(N)=CC=C1NC(=O)C1=CC=C(N)C=C1Cl UNLDYLKYVUHALD-UHFFFAOYSA-N 0.000 description 1
- XPAQFJJCWGSXGJ-UHFFFAOYSA-N 4-amino-N-(4-aminophenyl)benzamide Chemical compound C1=CC(N)=CC=C1NC(=O)C1=CC=C(N)C=C1 XPAQFJJCWGSXGJ-UHFFFAOYSA-N 0.000 description 1
- SKDHHIUENRGTHK-UHFFFAOYSA-N 4-nitrobenzoyl chloride Chemical compound [O-][N+](=O)C1=CC=C(C(Cl)=O)C=C1 SKDHHIUENRGTHK-UHFFFAOYSA-N 0.000 description 1
- 229940036592 ANTHELMINTICS Drugs 0.000 description 1
- 229960005069 Calcium Drugs 0.000 description 1
- VKGYPSJNXHGXOT-UHFFFAOYSA-N N(=C=S)C=1C=C(C(=O)NC2=CC(=CC=C2)N=C=S)C=CC1 Chemical compound N(=C=S)C=1C=C(C(=O)NC2=CC(=CC=C2)N=C=S)C=CC1 VKGYPSJNXHGXOT-UHFFFAOYSA-N 0.000 description 1
- XQJSVALKNSVMJN-UHFFFAOYSA-N N(=C=S)C=1C=C(C(=O)NC2=CC=CC=C2)C=CC1 Chemical compound N(=C=S)C=1C=C(C(=O)NC2=CC=CC=C2)C=CC1 XQJSVALKNSVMJN-UHFFFAOYSA-N 0.000 description 1
- NKUBAGAPNKVLDT-NFFVHWSESA-N N-[4-[(2Z)-2-(6-oxo-3-phenylcyclohexa-2,4-dien-1-ylidene)hydrazinyl]phenyl]benzamide Chemical compound C=1C=CC=CC=1C(=O)NC(C=C1)=CC=C1N\N=C(C(C=C1)=O)\C=C1C1=CC=CC=C1 NKUBAGAPNKVLDT-NFFVHWSESA-N 0.000 description 1
- WKEDVNSFRWHDNR-UHFFFAOYSA-N Salicylanilide Chemical compound OC1=CC=CC=C1C(=O)NC1=CC=CC=C1 WKEDVNSFRWHDNR-UHFFFAOYSA-N 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 239000000921 anthelmintic agent Substances 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 125000004432 carbon atoms Chemical group C* 0.000 description 1
- 230000000973 chemotherapeutic Effects 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- 238000010908 decantation Methods 0.000 description 1
- 125000003963 dichloro group Chemical group Cl* 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229910001867 inorganic solvent Inorganic materials 0.000 description 1
- 239000003049 inorganic solvent Substances 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L na2so4 Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/12—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by halogen atoms or by nitro or nitroso groups
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 |
|---|---|
| BE637472A true BE637472A (ru) |
Family
ID=202986
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BE637472D BE637472A (ru) |
Country Status (1)
| Country | Link |
|---|---|
| BE (1) | BE637472A (ru) |
-
0
- BE BE637472D patent/BE637472A/fr unknown
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