GB1215396A - Production of monothio-oxamic acid compounds - Google Patents
Production of monothio-oxamic acid compoundsInfo
- Publication number
- GB1215396A GB1215396A GB1862368A GB1862368A GB1215396A GB 1215396 A GB1215396 A GB 1215396A GB 1862368 A GB1862368 A GB 1862368A GB 1862368 A GB1862368 A GB 1862368A GB 1215396 A GB1215396 A GB 1215396A
- Authority
- GB
- United Kingdom
- Prior art keywords
- acid
- monothio
- amine
- oxamic
- general formula
- 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.)
- Expired
Links
- 238000004519 manufacturing process Methods 0.000 title abstract 2
- 239000002253 acid Substances 0.000 abstract 7
- PJKKDRZVAVHJNB-UHFFFAOYSA-N 2-amino-2-sulfanylideneacetamide Chemical class NC(=O)C(N)=S PJKKDRZVAVHJNB-UHFFFAOYSA-N 0.000 abstract 3
- 150000001412 amines Chemical class 0.000 abstract 3
- 239000011230 binding agent Substances 0.000 abstract 3
- 125000001931 aliphatic group Chemical group 0.000 abstract 2
- 125000003118 aryl group Chemical group 0.000 abstract 2
- 150000003839 salts Chemical class 0.000 abstract 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical class [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 abstract 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract 1
- 239000005864 Sulphur Substances 0.000 abstract 1
- 150000001298 alcohols Chemical class 0.000 abstract 1
- 229910052783 alkali metal Inorganic materials 0.000 abstract 1
- 150000001340 alkali metals Chemical class 0.000 abstract 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 abstract 1
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 abstract 1
- 229910000287 alkaline earth metal oxide Inorganic materials 0.000 abstract 1
- 150000001342 alkaline earth metals Chemical class 0.000 abstract 1
- 150000001408 amides Chemical class 0.000 abstract 1
- 150000003863 ammonium salts Chemical class 0.000 abstract 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 150000002170 ethers Chemical class 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 125000000623 heterocyclic group Chemical group 0.000 abstract 1
- 229910000039 hydrogen halide Inorganic materials 0.000 abstract 1
- 239000012433 hydrogen halide Substances 0.000 abstract 1
- 150000004679 hydroxides Chemical class 0.000 abstract 1
- 150000007529 inorganic bases Chemical class 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 229910052757 nitrogen Inorganic materials 0.000 abstract 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 abstract 1
- 239000003960 organic solvent Substances 0.000 abstract 1
- 150000007519 polyprotic acids Polymers 0.000 abstract 1
- 239000007858 starting material Substances 0.000 abstract 1
- 150000003512 tertiary amines Chemical class 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
- C07D295/18—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carboxylic acids, or sulfur or nitrogen analogues thereof
- C07D295/194—Radicals derived from thio- or thiono carboxylic acids
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
1,215,396. Monothio-oxamic acid compounds. BADISCHE ANILIN- & SODA-FABRIK A.G. 19 April, 1968 [21 April, 1967], No. 18623/68. Heading C2C. Monothio-oxamic acid amides of general formula where R<SP>1</SP> and R<SP>2</SP>, which may be the same or different, may be aliphatic, cycloaliphatic, araliphatic or aromatic, or R<SP>1</SP> denotes such a radical and R<SP>2</SP> denotes H, or R<SP>1</SP> with R<SP>2</SP> and the adjacent nitrogen may be a heterocyclic ring, and R<SP>3</SP> may be the radical -NH 2 or -OR<SP>4</SP>, where R<SP>4</SP> may be H, aliphatic, cycloaliphatic, araliphatic or aromatic, are prepared by reacting a haloacetic acid compound of the general formula where R<SP>1</SP>, R<SP>2</SP> and R<SP>3</SP> have the same meaning as above, R<SP>5</SP> may be a halogen atom, R<SP>6</SP> and R<SP>7</SP> may be H or halogen, with elemental sulphur and an amine having the general formula where R<SP>1</SP> and R<SP>2</SP> have the above meanings, in the presence of an acid-binding agent which may be identical with the amine, the amounts of amine and acid-binder being selected so as to favour the production of the desired product monothio-oxamic acid amide as compared to the undesired monothio-oxamic acid amide. The free haloacetic acid may be replaced by a salt of a haloacetic acid with an alkali metal, alkaline earth metal, unsubstituted ammonium or substituted ammonium cation and the process may be carried out in an inert organic solvent, e.g. alcohols, ethers or aromatic hydrocarbons at a temperature of 20-200‹ C., and preferably 50-150‹ C. Acid-binding agents such as tertiary amines, inorganic bases such as alkaline earth metal oxides, hydroxides or amides, alcoholates or salts of polybasic acids may be added to bind the acid present in the reaction, e.g. haloacetic acid as starting material or hydrogen halide formed.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEP1270A DE1270552B (en) | 1967-04-21 | 1967-04-21 | Process for the preparation of monothione oxalic acid amides |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1215396A true GB1215396A (en) | 1970-12-09 |
Family
ID=6986241
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB1862368A Expired GB1215396A (en) | 1967-04-21 | 1968-04-19 | Production of monothio-oxamic acid compounds |
Country Status (6)
| Country | Link |
|---|---|
| BE (1) | BE713737A (en) |
| CH (1) | CH495340A (en) |
| DE (1) | DE1270552B (en) |
| FR (1) | FR1557489A (en) |
| GB (1) | GB1215396A (en) |
| NL (1) | NL6805585A (en) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2460909C2 (en) * | 1974-12-21 | 1986-02-27 | Bayer Ag, 5090 Leverkusen | Process for the preparation of alpha-oxothiodimethylamides |
| DE68910021T2 (en) * | 1988-07-04 | 1994-05-11 | Meiji Seika Kaisha | Oxamic acid compounds and pharmaceutical compositions for use in improving damaged brain functions. |
| US5232947A (en) * | 1988-07-04 | 1993-08-03 | Meiji Seika Kaisha, Ltd. | Oxamic acid compounds and pharmaceutical composition for use in improvement of damaged cerebral functions of brain |
| WO2001028991A1 (en) * | 1999-10-19 | 2001-04-26 | Taisho Pharmaceutical Co., Ltd | N-cycloalkyl thiooxamide derivatives |
-
1967
- 1967-04-21 DE DEP1270A patent/DE1270552B/en active Granted
-
1968
- 1968-03-27 FR FR1557489D patent/FR1557489A/fr not_active Expired
- 1968-04-16 BE BE713737D patent/BE713737A/xx unknown
- 1968-04-18 CH CH572768A patent/CH495340A/en not_active IP Right Cessation
- 1968-04-19 GB GB1862368A patent/GB1215396A/en not_active Expired
- 1968-04-19 NL NL6805585A patent/NL6805585A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DE1270552C2 (en) | 1969-01-16 |
| FR1557489A (en) | 1969-02-14 |
| NL6805585A (en) | 1968-10-22 |
| DE1270552B (en) | 1968-06-20 |
| CH495340A (en) | 1970-08-31 |
| BE713737A (en) | 1968-10-16 |
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