CA1162926A - Process for the manufacture of 3-acylazo-propionic acid esters and isomers thereof - Google Patents
Process for the manufacture of 3-acylazo-propionic acid esters and isomers thereofInfo
- Publication number
- CA1162926A CA1162926A CA000381868A CA381868A CA1162926A CA 1162926 A CA1162926 A CA 1162926A CA 000381868 A CA000381868 A CA 000381868A CA 381868 A CA381868 A CA 381868A CA 1162926 A CA1162926 A CA 1162926A
- Authority
- CA
- Canada
- Prior art keywords
- general formula
- acid ester
- compound
- range
- carried out
- 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
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
- C07D285/01—Five-membered rings
- C07D285/02—Thiadiazoles; Hydrogenated thiadiazoles
- C07D285/04—Thiadiazoles; Hydrogenated thiadiazoles not condensed with other rings
- C07D285/06—1,2,3-Thiadiazoles; Hydrogenated 1,2,3-thiadiazoles
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
3-Acylazo-propionic acid esters of the general formula I
(I) and isomers thereof (in which R1 represents C1-C6-alkyl and R2 represents alkoxy or amino), suitable as starting materials for the manufacture of 1,2,3-thiadiazole-5-car-boxylic acid derivatives, are prepared by a process which comprises reacting an acrylic acid ester of the general formula H2C = CH - COOR1 with a hydrazine derivative of the general formula H2N - NH - CO -R2 to form a 3-acylhydra-zino-propionic acid ester of the general formula
(I) and isomers thereof (in which R1 represents C1-C6-alkyl and R2 represents alkoxy or amino), suitable as starting materials for the manufacture of 1,2,3-thiadiazole-5-car-boxylic acid derivatives, are prepared by a process which comprises reacting an acrylic acid ester of the general formula H2C = CH - COOR1 with a hydrazine derivative of the general formula H2N - NH - CO -R2 to form a 3-acylhydra-zino-propionic acid ester of the general formula
Claims (24)
1. A process for the manufacture of a compound se-lected from a 3-acylazo-propionic acid ester of the general formula I
(I), in which R1 represents a C1-C6-alkyl group and R2 represents an alkoxy group or an amino group, and isomers thereof of the general formula V
(V), in which R1 and R2 have the meanings given above, and of the general formula VI
(VI), in which R1 and R2 have the meanings given above, which com-prises reacting an acrylic acid ester of the general formula II
(II), in which R1 has the meaning given above, with a hydrazine derivative of the general formula III
H2N - NH - CO - R2 (III), in which R2 has the meaning given above, to form a 3-acyl-hydrazino-propionic acid ester of the general formula IV
(IV), . 25 .
in which R1 and R2 have the meanings given above, and oxi-dizing this compound of the general formula IV in an inert solvent with an oxidizing agent.
(I), in which R1 represents a C1-C6-alkyl group and R2 represents an alkoxy group or an amino group, and isomers thereof of the general formula V
(V), in which R1 and R2 have the meanings given above, and of the general formula VI
(VI), in which R1 and R2 have the meanings given above, which com-prises reacting an acrylic acid ester of the general formula II
(II), in which R1 has the meaning given above, with a hydrazine derivative of the general formula III
H2N - NH - CO - R2 (III), in which R2 has the meaning given above, to form a 3-acyl-hydrazino-propionic acid ester of the general formula IV
(IV), . 25 .
in which R1 and R2 have the meanings given above, and oxi-dizing this compound of the general formula IV in an inert solvent with an oxidizing agent.
2. A process as claimed in claim 1, wherein R2 represents a C1-C4-alkoxy group.
3. A process as claimed in claim 1 or 2, wherein the reaction of the acrylic acid ester of the general formula II with the hydrazine derivative of the general formula III
is carried out in an inert solvent.
is carried out in an inert solvent.
4. A process as claimed in claim 1, wherein the reaction of the acrylic acid ester of the general formula II with the hydrazine derivative of the general formula III
is carried out in the presence of a catalyst.
is carried out in the presence of a catalyst.
5. A process as claimed in claim 4, wherein the cata-lyst is a basic or an acidic catalyst.
6. A process as claimed in claim 1, wherein the reaction of the acrylic acid ester of the general formula II
with the hydrazine derivative of the general formula III
is carried out at a temperature within the range of from -20°C to 150°C.
with the hydrazine derivative of the general formula III
is carried out at a temperature within the range of from -20°C to 150°C.
7. A process as claimed in claim 6, wherein the temperature is within the range of from 0°C to 50°C.
8. A process as claimed in claim 1, wherein the reac-tion of the acrylic acid ester of the general formula II
with the hydrazine derivative of the general formula III is carried out at a pressure within the range of from 1 to 10 atmospheres.
with the hydrazine derivative of the general formula III is carried out at a pressure within the range of from 1 to 10 atmospheres.
9. A process as claimed in claim 8, wherein the . 26 .
pressure is 1 atmosphere.
pressure is 1 atmosphere.
10. A process as claimed in claim 1 or 2, wherein approximately equimolar amounts of the acrylic acid ester of the general formula II and of the hydrazine derivative of of the general formula III are used.
11. A process as claimed in claim 1, wherein the oxidation of the 3-acylhydrazino-propionic acid ester of the general formula IV is carried out with a conventional oxidizing agent at a temperature within the range of from -20°C to 100°C.
12. A process as claimed in claim 11, wherein the temperature is within the range of from -5°C to 50°C.
13. A process as claimed in claim 1 or 2, wherein the 3-acylhydrazino-propionic acid ester of the general formula IV is not isolated from the reaction mixture in which it is formed, and the formation of this ester and the oxi-dation thereof is a continuous process.
14. A process as claimed in claim 1, wherein a resulting compound of the general formula I is rearranged to form a compound of the general formula V and/or a com-pound of the general formula VI by treatment with a catalyst.
15. A process as claimed in claim 14, wherein the catalyst is an acid or a Lewis acid.
16. A process as claimed in claim 14, wherein the catalyst is a base.
17. A process as claimed in claim 14, 15 or 16, wherein the rearrangement is carried out in a solvent.
.27.
.27.
18. A process as claimed in claim 14, wherein the rearrangement is carried out at a temperature within the range of from -20°C to 50°C to form a compound of the general formula V and a compound of the general formula VI.
19. A process as claimed in claim 18, wherein the temperature is within the range of frorn 0°C to 30°C.
20. A process as claimed in claim 1, wherein a resulting compound of the general formula I is reacted with thionyl chloride of the formula SOCl2 to form a 1,2,3-thia-diazole-5-carboxylic acid derivative of the general formula VII
(VII), in which R1 represents a C1-C6-alkyl group.
(VII), in which R1 represents a C1-C6-alkyl group.
21. A process as claimed in claim 20, wherein the reaction is carried out at a temperature within the range of from -20°C to 100°C.
22. A proeess as claimed in claim 21, wherein the temperature is within the range of from -5°C to 50°C.
23. A process as claimed in any one of claims 20, 21 or 22, wherein the molar ratio of the compound of the general formula I to the thionyl chloride used for the re-action is 1 : 3.
24. A process as claimed in claim 1, wherein a re-sulting compound of the general formula V and/or a resulting . 28 .
compound of the general formula VI is/are reacted with thionyl chloride of the formula SOCl2 to form a 1,2,3-thiadiazole 5-carboxylic acid derivative of the general formula VII
(VII), in which R1 represents a C1-C6-alkyl group.
. 29.
compound of the general formula VI is/are reacted with thionyl chloride of the formula SOCl2 to form a 1,2,3-thiadiazole 5-carboxylic acid derivative of the general formula VII
(VII), in which R1 represents a C1-C6-alkyl group.
. 29.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19803029375 DE3029375A1 (en) | 1980-07-31 | 1980-07-31 | METHOD FOR PRODUCING 3-ACYLAZOPROPIONIC ACID ESTERS |
| DEP3029375.5 | 1980-07-31 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1162926A true CA1162926A (en) | 1984-02-28 |
Family
ID=6108760
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000381868A Expired CA1162926A (en) | 1980-07-31 | 1981-07-16 | Process for the manufacture of 3-acylazo-propionic acid esters and isomers thereof |
Country Status (35)
| Country | Link |
|---|---|
| JP (1) | JPS606938B2 (en) |
| KR (1) | KR840002326B1 (en) |
| AR (1) | AR226118A1 (en) |
| AT (1) | AT375636B (en) |
| AU (1) | AU540087B2 (en) |
| BE (1) | BE889805A (en) |
| BR (1) | BR8104912A (en) |
| CA (1) | CA1162926A (en) |
| CH (1) | CH646417A5 (en) |
| CS (1) | CS224619B2 (en) |
| DD (1) | DD202004A5 (en) |
| DE (1) | DE3029375A1 (en) |
| DK (1) | DK293281A (en) |
| EG (1) | EG15225A (en) |
| ES (1) | ES504223A0 (en) |
| FI (1) | FI812302L (en) |
| FR (1) | FR2487825A1 (en) |
| GB (1) | GB2081265B (en) |
| GR (1) | GR78232B (en) |
| HU (1) | HU182364B (en) |
| IE (1) | IE51456B1 (en) |
| IL (1) | IL63440A (en) |
| IT (1) | IT1142034B (en) |
| LU (1) | LU83517A1 (en) |
| MX (1) | MX6766E (en) |
| NL (1) | NL8102925A (en) |
| NZ (1) | NZ197844A (en) |
| PH (1) | PH18326A (en) |
| PL (1) | PL129167B1 (en) |
| PT (1) | PT73444B (en) |
| RO (1) | RO82381A (en) |
| SE (1) | SE8104388L (en) |
| YU (1) | YU41251B (en) |
| ZA (1) | ZA815289B (en) |
| ZW (1) | ZW18281A1 (en) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4454336A (en) * | 1982-09-27 | 1984-06-12 | American Cyanamid Company | Derivatives of 3-(formylmethylthio)-propanoate |
| JPS60164379U (en) * | 1984-04-09 | 1985-10-31 | ジューキ株式会社 | Safety mechanism of sewing machine thread cutting device |
| JP2584981Y2 (en) * | 1992-06-30 | 1998-11-11 | ジューキ株式会社 | Sewing machine thread trimmer |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2728523C2 (en) * | 1977-06-23 | 1986-02-27 | Schering AG, 1000 Berlin und 4709 Bergkamen | 4-Methyl-1,2,3-thiadiazole-5-carboxylic acid (cyclohexylmethyl) amide, agents having a herbicidal and growth-regulating action, containing this compound and a process for its preparation |
-
1980
- 1980-07-31 DE DE19803029375 patent/DE3029375A1/en not_active Withdrawn
-
1981
- 1981-06-16 CH CH396681A patent/CH646417A5/en not_active IP Right Cessation
- 1981-06-17 NL NL8102925A patent/NL8102925A/en not_active Application Discontinuation
- 1981-07-02 DK DK293281A patent/DK293281A/en not_active Application Discontinuation
- 1981-07-02 YU YU1638/81A patent/YU41251B/en unknown
- 1981-07-15 SE SE8104388A patent/SE8104388L/en not_active Application Discontinuation
- 1981-07-16 CA CA000381868A patent/CA1162926A/en not_active Expired
- 1981-07-22 FI FI812302A patent/FI812302L/en not_active Application Discontinuation
- 1981-07-23 ES ES504223A patent/ES504223A0/en active Granted
- 1981-07-23 IT IT23083/81A patent/IT1142034B/en active
- 1981-07-27 NZ NZ197844A patent/NZ197844A/en unknown
- 1981-07-27 GB GB8123067A patent/GB2081265B/en not_active Expired
- 1981-07-27 RO RO81104983A patent/RO82381A/en unknown
- 1981-07-28 IL IL63440A patent/IL63440A/en unknown
- 1981-07-28 AT AT0332681A patent/AT375636B/en not_active IP Right Cessation
- 1981-07-28 PT PT73444A patent/PT73444B/en unknown
- 1981-07-28 PH PH25973A patent/PH18326A/en unknown
- 1981-07-28 DD DD81232152A patent/DD202004A5/en unknown
- 1981-07-29 EG EG81438A patent/EG15225A/en active
- 1981-07-29 LU LU83517A patent/LU83517A1/en unknown
- 1981-07-29 PL PL1981232401A patent/PL129167B1/en unknown
- 1981-07-30 JP JP56118589A patent/JPS606938B2/en not_active Expired
- 1981-07-30 CS CS815801A patent/CS224619B2/en unknown
- 1981-07-30 IE IE1734/81A patent/IE51456B1/en unknown
- 1981-07-30 HU HU812226A patent/HU182364B/en not_active IP Right Cessation
- 1981-07-30 BE BE0/205539A patent/BE889805A/en not_active IP Right Cessation
- 1981-07-30 FR FR8114836A patent/FR2487825A1/en active Granted
- 1981-07-30 GR GR65666A patent/GR78232B/el unknown
- 1981-07-30 MX MX819585U patent/MX6766E/en unknown
- 1981-07-30 BR BR8104912A patent/BR8104912A/en unknown
- 1981-07-31 ZW ZW182/81A patent/ZW18281A1/en unknown
- 1981-07-31 AU AU73601/81A patent/AU540087B2/en not_active Ceased
- 1981-07-31 KR KR1019810002794D patent/KR840002326B1/en active
- 1981-07-31 ZA ZA815289A patent/ZA815289B/en unknown
- 1981-07-31 AR AR286297A patent/AR226118A1/en active
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |