IE40293B1 - Ethyl (2-acetoaceylaminothiazolyl-(4)7-acetate and a proceess for the preparation thereof - Google Patents
Ethyl (2-acetoaceylaminothiazolyl-(4)7-acetate and a proceess for the preparation thereofInfo
- Publication number
- IE40293B1 IE40293B1 IE252474A IE252474A IE40293B1 IE 40293 B1 IE40293 B1 IE 40293B1 IE 252474 A IE252474 A IE 252474A IE 252474 A IE252474 A IE 252474A IE 40293 B1 IE40293 B1 IE 40293B1
- Authority
- IE
- Ireland
- Prior art keywords
- acetate
- ethyl
- process according
- solvent
- preparation
- Prior art date
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three 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, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D277/38—Nitrogen atoms
- C07D277/44—Acylated amino or imino radicals
- C07D277/46—Acylated amino or imino radicals by carboxylic acids, or sulfur or nitrogen analogues thereof
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
1428600 Plant growth regulant LONZA Ltd 9 Dec 1974 [11 Dec 1973] 53079/74 Heading C1B [Also in Division C2] Examples describe the use of the novel compound ethyl-[2-acetoacetylaminothiazolyl- (4)]-acetate and for comparison purposes, indolyl acetic acid, as plant growth regulants.
[GB1428600A]
Description
40 293 i
"I
The prcaent Invention is: tumctv.uiNl wIt;!i ^thyl/T-ncfto-acotyl^^^inothiu^oly^-(/Jj7~iW!u^;,aiu* wlt!i thi; preparation ' thereof. >
The ethyl ^~2-acotoacotylaminothia2olyi-(/»J7-acetatc provided according to the present Invention- is useful as an intoroedlato for the production of dye pigments and is also
* ' . - '
effective as a photopolycerlsation initiator* Furthermore, it possesses planL growth—stimulating properties.
According to the present invention, ethyl /~2-aceto-acetylaminothiazolyl-(4}7-acetate can be prepared by reacting ethyl £2-iiminothiazolyl-'(4j7-acetate in an organic solvent
• |
in tho presence of 5 - 1556 by weight glacial acetic acid, referred to the amount of solvent used, with diketene at a temperature of 30 to 80°C.
The ethyl 2-ominothiazolyl- (4J7-acetate used as starting material can be prepared in known manner by the reaction of ethyl Jf-chloroacetoacetate with thiourea (see Bellstein Hw 663 and Beilstoin Hw 22, 336).
The organic solvent used can be an alkyl ester of acetic acid which contains up to 4 carbon atoms in the alkyl radical, for example butyl acetate, or an aromatic hydrocarbon, for example toluene, or a halogenated hydrocarbon, for example carbon tetrachloride.
It is important to carry out the reaction with diketene in the presence of 5 - 1596 by weight and preferably of 8 to 12% by weight glacial acetic acid, referred to the amount of solvent used.
The reaction is, as mentioned above, carried out at a o ' o temperature of 30 to 80 C., and preferably of 50 to 60 C.
The present invention also provides compositions for the stimulation of the growth of plants, comprising ethyl /~2-aceto-
40293
acotylaminothiazolyl-(4J7-acs'tate» in admixture with a solid or liquid diluent or carrier.
The following Example Is given for the purpose of illustrating the present invention Example
18.6 g. ethyl /~2-aminothiazolyl-(4J7_acetate, dissolved in 50 ml. butyl acetate and 5 nl. glacial acetic acid, are placed in a 250 ml. 3-necked flask equipped with a stirrer, reflux condenser, thermometer and heating mantle and heated to 50°C., while stirring. Thereafter, while the temperature increases to 55 -60°C., 6.7 g. diketene are added dropwise. When the addition of the diketene is completed, the reaction mixture is stirred for a further 2 hours, while maintaining the.temperature at 55 - 60°C. After cooling, the crystals obtained are filtered off, the mother liquor is evaporated and the crystals thereby obtained are isolated. After washing and drying in a vacuum at 60 - 70°C., 22.8 g. of the desired prqduct are obtained. This corresponds to a yield of 84.4# of theory of ethyl ^2-acetoacetylaminothiazolyl-(4j7-acetate, referred to the amount of aminothiazole used.
Instead of butyl acetate, there can also be used, as solvent, toluene or carbon tetrachloride, in which case,the yields obtained are 76.3# and 71.55* of theory, respectively.
Pure ethyl /2-acetoacetylaminothiazolyl-(4J7~acetate has a melting point of 133 - 135°C.
Analysis;
C^H^NgO^S (M.V. 270)
found: C 48.1#;H 5.1# ; N 10.1% ; S 13.1#
calc : 48.e7#; 5 . 2394; 10.37#; 11.86#
The IR, NKR and MS spectra confirm the structure of the product.
- 3 -
4 0 2 0 3
The growth r.timulalintf activity of the now compound according to the present invention was determined in the following manner:
Wheat seeds were applied to filter.paper and kept in a warin cabinet in the dark at 24°C., until they had germinated. When the seedlings were 25 - 35 mm. long pieces of caleoptile of 9 mm. length were removed at a distance of about 3 - 5 nun. from the tip and placed in distilled water for 2 hours. Thereafter, tho pieces of caleoptile were introduced into Petri dishes containing solutions of the active materials to be tested. The longitudinal growth was determined after 24 hours. Distilled water was used as control and ,a3 comparison growth stimulating substance, indolyl-acetic acid was used. The results obtained are set out in the following Table:
TABLE
active substance concentration in mol
1 x 10~3
1 x 10-4
1 x 10-5
ethyl /2-acetoacetyl-
aminothiazolyl-(4J/-
114
114
109
acetate
indolyl-acetic acid
91
120
125
The longitudinal growth of the control (distilled water) was taken as being 100.
Claims (12)
1. Ethyl /2-acetoacetylarair.othiazolyl-('»_27-scetate.
2. Process for the preparation of ethyl /J-acetoacety-laninothiazolyl-(4j7-acetate, wherein ethyl ^3-aminothiazolyl- ■. (4J7-acetate is rcuctcd in an organic solvent, in the proaenco of 5 to 15t'» by weight glacial acetic acid, referred to tho solvent, with diketene at a temperature of 30 - 00°C.
3* Process according to claim 2, wherein the reaction is carried out at a temperature of 50 - 60°C.;I;u»
4. Process according to claim 2 or 3, wherein the glacial acetic acid is used in an amount of 8 - 129£ by weight,;referred to the solvent.;
5. Prpcess according to any of claims 2-4, wherein the solvent used is an alkyl acetate containing up to 4 carbon i .*» atoms in the alkyl radical.
6. Process according to claim 5, wherein the alkyl acetate is butyl acetate.
7. Process according to any of claims 2-4, wherein the solvent used is an aromatic hydrocarbon.
'» 8. Process according to claim 7, wherein the aromatic hydrocarbon is toluene.
9. Process according to any of claims 2-4, wherein the solvent used is a halogenated hydrocarbon.
10. Process according to claim 9, wherein the halogenated hydrocarbon is carbon tetrachloride.
11. Process for the preparation of ethyl ^?-acetoacetylamino-thiazolyl-(4J7~acetate, substantially as hereinbefore described and exemplified.
12. Ethyl /2-acetoacetylaininothiazolyl-(4_)7_acetate, whenever ; prepared by the process according to any of claims 2 to 11. - 5 - 40293 \j. (:o;;i;jo.:it.io:u: Tor llu- .sLiiuilulion 1' 'il.irit ^i-owih, comprising ethyl /?-acotoacotylcninothia2olyl-(^<)7-acctatc, in admixture v/ith a solid or liquid diluent or carrier. Dated tliis the 6th day of December, 1974 P. R. KELLY & CO. BY: V.C. ^00t0^ EXECUTIVE 27 Clyde Road, BallsJXTdge, Dublin 4< AGHNTS I'OR THE A^ClCANTS - 6 -
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1730373A CH582685A5 (en) | 1973-12-11 | 1973-12-11 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IE40293L IE40293L (en) | 1975-06-11 |
| IE40293B1 true IE40293B1 (en) | 1979-04-25 |
Family
ID=4424362
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE252474A IE40293B1 (en) | 1973-12-11 | 1974-12-06 | Ethyl (2-acetoaceylaminothiazolyl-(4)7-acetate and a proceess for the preparation thereof |
Country Status (15)
| Country | Link |
|---|---|
| JP (1) | JPS5089368A (en) |
| AT (1) | AT338260B (en) |
| BE (1) | BE823236A (en) |
| CA (1) | CA1048036A (en) |
| CH (1) | CH582685A5 (en) |
| CS (1) | CS181775B2 (en) |
| DD (1) | DD115678A5 (en) |
| DE (1) | DE2457689A1 (en) |
| FR (1) | FR2253746A1 (en) |
| GB (1) | GB1428600A (en) |
| IE (1) | IE40293B1 (en) |
| IT (1) | IT1024395B (en) |
| LU (1) | LU71462A1 (en) |
| NL (1) | NL7416117A (en) |
| SU (1) | SU511859A3 (en) |
-
1973
- 1973-12-11 CH CH1730373A patent/CH582685A5/xx not_active IP Right Cessation
-
1974
- 1974-12-06 DE DE19742457689 patent/DE2457689A1/en active Pending
- 1974-12-06 IE IE252474A patent/IE40293B1/en unknown
- 1974-12-09 GB GB5307974A patent/GB1428600A/en not_active Expired
- 1974-12-09 SU SU2080927A patent/SU511859A3/en active
- 1974-12-09 JP JP14194774A patent/JPS5089368A/ja active Pending
- 1974-12-10 CS CS841074A patent/CS181775B2/en unknown
- 1974-12-10 IT IT5446474A patent/IT1024395B/en active
- 1974-12-10 CA CA215,606A patent/CA1048036A/en not_active Expired
- 1974-12-10 DD DD18289674A patent/DD115678A5/xx unknown
- 1974-12-11 BE BE151406A patent/BE823236A/en unknown
- 1974-12-11 AT AT988574A patent/AT338260B/en not_active IP Right Cessation
- 1974-12-11 LU LU71462A patent/LU71462A1/xx unknown
- 1974-12-11 FR FR7440861A patent/FR2253746A1/fr not_active Withdrawn
- 1974-12-11 NL NL7416117A patent/NL7416117A/en not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| DE2457689A1 (en) | 1975-06-12 |
| LU71462A1 (en) | 1975-08-20 |
| BE823236A (en) | 1975-06-11 |
| CS181775B2 (en) | 1978-03-31 |
| CH582685A5 (en) | 1976-12-15 |
| AT338260B (en) | 1977-08-10 |
| ATA988574A (en) | 1976-12-15 |
| DD115678A5 (en) | 1975-10-12 |
| NL7416117A (en) | 1975-06-13 |
| IE40293L (en) | 1975-06-11 |
| GB1428600A (en) | 1976-03-17 |
| CA1048036A (en) | 1979-02-06 |
| JPS5089368A (en) | 1975-07-17 |
| IT1024395B (en) | 1978-06-20 |
| FR2253746A1 (en) | 1975-07-04 |
| SU511859A3 (en) | 1976-04-25 |
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