GB2202224A - Benzodioxole derivative useful as an intermediate - Google Patents
Benzodioxole derivative useful as an intermediate Download PDFInfo
- Publication number
- GB2202224A GB2202224A GB08807566A GB8807566A GB2202224A GB 2202224 A GB2202224 A GB 2202224A GB 08807566 A GB08807566 A GB 08807566A GB 8807566 A GB8807566 A GB 8807566A GB 2202224 A GB2202224 A GB 2202224A
- Authority
- GB
- United Kingdom
- Prior art keywords
- compound
- benzodioxole
- formula
- preparation
- derivative useful
- 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.)
- Granted
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D317/46—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with one six-membered ring
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
- A01N43/24—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with two or more hetero atoms
- A01N43/26—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with two or more hetero atoms five-membered rings
- A01N43/28—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with two or more hetero atoms five-membered rings with two hetero atoms in positions 1,3
- A01N43/30—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with two or more hetero atoms five-membered rings with two hetero atoms in positions 1,3 with two oxygen atoms in positions 1,3, condensed with a carbocyclic ring
Description
CHEMICAL COMPOUND
The present invention relates to a novel benzodioxole compound and its preparation. The novel compound is a valuable intermediate for the synthesis of biocidal compounds.
Accordingly the present invention provides the compound of formula I
The compound is prepared by Hofmann degradation, i.e. by reacting 2,2-difluoro-4-carbamoyl-1 ,3-benzodioxole with bromine, in the presence of aqueous alkali metal hydroxide.
CONH2 NH2 t3C X Br2 X; ( I ) O F hydroxide O F hydroxide This process is carried out in accordance with the method of
L.M. Yagupolskii et al., Zhur. Obshch. Khym. 31, 628 (1981).
The precursors for the preparation of the compound of formula I are synthesised as follows starting from 4-carboxy-1,3benzodioxole (in accordance with W.H. Perkin and V.M. Trikojus,
J. Chem. Soc. 1926, 2925):
The compound of the present invention is particularly useful for preparing the compound of formula II
by reacting the compound of formula I with the compound of formula III
in the presence of an acid acceptor in an inert solvent or diluent.
The compound of formula (II) its preparation and use are described and claimed in copending application No. 8607566 (Serial No. 2173793).
The invention is illustrated in more detail by the follwoing
Examples.
Example 1.1
Preparation of 2,2-difluoro-4-amino-1,3-benzodioxole
52.5g of bromine are added dropwise at 0 C to a solution of 120g of potassium hydroxide in 780 ml of water. Subsequently, 50.8g of 2,2-difluoro-4-carbamoyl-1,3-benzodioxole are added, and the reaction mixture is stirred for 30 minutes at room temperature and then heated for 45 minutes to 800C. The reaction solution is then diluted in 400 ml of water and distilled with steam. The distillate is extracted with diethyl ether and dried over sodium sulfate. The solvent is evaporated off, affording 38.1g of the title compund as a yellowish oil with a refractive index nD21 of 1.4955.
Example 1.2:
Preparation of 2,2-dichloro-4-carbonyl chloride-1 ,3-benzodioxole
40g of 4-carboxy-1,3-benzodioxole are mixed with 150g of phosphorus pentachloride, and the mixture is heated to 70"C.
After 3.5 hours, the temperature is increased to 900C and then held at this level of 12 hours. Subsequently, the volatile components are distilled off at 110C and 2000 Pa, and the residue is distilled off under high vacuum, affording 45g of the title compound as a slightly yellowish solid.
Example 1.3
Preparation of 2,2-difluoro-4-carbonyl fluoride 1 ,3-benzodioxole
In a distillation apparatus, 55.7g of SbF3 are added to 59.4g of 2,2-dichloro-4-carbonyl chloride 1 ,3-benzodioxole, whereupon a reaction takes place immediately. In-order to maintain the reaction, the temperature is slowly increased, while simultaneously gradually evacuating. 59.5g of a red oil distill over at 105-1170C and 6666 Pa. The distillate is taken up in 100 ml of diethyl ether and washed with two 150 ml portions of semiconcentrated hydrochloric acid and then with water. The ether solution is dried over sodium sulfate and the solvent is evaporated off, affording 42.0g of the title compound.
Example 1.4
Preparation of 2,2-difluoro-4-carbamoyl-1 ,3-benzodioxole
With ice cooling and stirring, 63.6g of a 2,2-difluoro4-carbonyl fluoride-1,3-benzodioxole are added dropwise to 120 ml of a concentrated 25 % solution of ammonia. In the course of several hours a crystalline slurry is formed which is then isolated by filtration and washed in succession with a dilute solution of ammonia and then with water, affording 51g of 2,2-difluoro-4-carbamoyl-1,3-benzodioxole with a melting point of 129.5-131"C.
Claims (3)
1. The compound of formula I
2. A process for the preparation of the compound of formula I, which process comprises subjecting the compound of the formula
to Hofmann degradation with bromine, in the presence of aqueous alkali metal hydroxide.
3. A process according to claim 2 substantially as hereinbefore described with reference to foregoing Example 1.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH143485 | 1985-04-03 | ||
| GB08607566A GB2173793B (en) | 1985-04-03 | 1986-03-26 | Pesticidal compositions |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| GB8807566D0 GB8807566D0 (en) | 1988-05-05 |
| GB2202224A true GB2202224A (en) | 1988-09-21 |
| GB2202224B GB2202224B (en) | 1989-01-25 |
Family
ID=25687637
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB08807566A Expired GB2202224B (en) | 1985-04-03 | 1986-03-26 | Benzodioxole derivative useful as an intermediate |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB2202224B (en) |
-
1986
- 1986-03-26 GB GB08807566A patent/GB2202224B/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| GB8807566D0 (en) | 1988-05-05 |
| GB2202224B (en) | 1989-01-25 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PCNP | Patent ceased through non-payment of renewal fee |
Effective date: 19930326 |