Process for producing the 3-chloro-1-formyl-4-phenylpyrroles

Details Process for producing the 3-chloro-1-formyl-4-phenylpyrroles Process for producing the 3-chloro-1-formyl-4-phenylpyrroles

1984-06-04

1986-06-10

Brust, Joseph D.

Organic compounds -- part of the class 532-570 series

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

548565, C07D20730

Patent

active

045944296

DESCRIPTION:

BRIEF SUMMARY
FIELD OF THE INVENTION

The present invention relates to a novel process for producing the 3-chloro-1-formyl-4-phenylpyrrole, as a useful fungicidal agent to agriculture and horticulture, which is represented by the general formula: ##STR2## wherein X denotes the same or different kind(s) of substituted groups being chosen from halogen atom, nitro group and/or trifluoromethyl group and n denotes zero or an integer of 1 or 2.


BACKGROUND OF THE INVENTION

In order to produce the compounds represented by the general formula [I], first a process is used which comprises synthesizing the pyrroles having the general formula [II]: ##STR3## and then, the compound having the general formula II is treated with a formulating step, as heretofore described in the prior art (U.S. Pat. No. 4,303,667).
In the general formula [II], X and n have the same significances defined above.
Further, as to the process for producing the said pyrroles having the general formula [II], the conventional process is set forth below in which taking into consideration the reactivity of the pyrrole, both .alpha.-positions of pyrrole are protected with easily separable protective groups and then its .beta.-position is treated with a chlorination step. This process is well known.
But, those conventional processes utilize numerous procedures and those operations involves difficult steps, so that those processes can not be said to be an industrially desirable method. ##STR4##


SUMMARY OF THE INVENTION

The manufacturing process by the present invention is to provide the method set forth in the following reaction formulae which comprises using 3-phenyl-2,2,4-trichlorobutanals as a raw material and obtaining a novel pyrroline derivative having the general formula: ##STR5## as an intermediate wherein X and n have the same significances defined above.
The said method aims to greatly curtail the production steps and to raise the rate of yield. ##STR6##


THE BEST MODE FOR CARRYING OUT THE INVENTION

In carrying out the present invention into practice, the compound having the general formula [IV] is made to react with ammonia gas or aqueous ammonia in an organic solvent at a temperature ranging from room temperature to 50.degree. C., desirably at about 40.degree. C. of temperature and thereby, the pyrroline derivative having the said general formula [III] is produced (the First Step).
Then, the said pyrroline derivative is made to react with a Vilsmeyer reagent in an organic solvent such as dimethylformamide or ethylene dichloride. (The Second Step).
The intermediate reaction compound obtained thereto is hydrolysed in water or an aqueous solution containing sodium acetate or sodium carbonate as the Third Step and thereby, the pyrrole derivative having the general formula [I] is produced.
As the solvent employable for the First Step, an inert solvent involving glyme, dioxane, ethylether, isopropylether, ethanol, propanol, benzene or the like is used, but ethers are desirably used.
As said Vilsmeyer's reagent used in the Second Step, the addition product which consists of one kind or more compound(s) of thionyl chloride, phosphorus oxychloride, oxalylchloride and/or phosgene with formamide derevative(s) involving N,N-dimethylformamide, N-formyl-morpholine or N-methylformamide are used, Desirably, the adduct material of phosphorus oxychloride and N,N-dimethylformamide is used.
As the said organic solvent, ethylene dichloride or chlorobenzene may be used and further by adding a surplus amount of dimethylformamide as the raw material, it may be simultaneously used as the solvent. The reaction is carried out at 70.degree. C. to 125.degree. C.
The usual Vilsmeyer's reaction in the hydrolysis of the Third Step is carried out with the heating and refluxing procedure in an alkaline solution containing sodium carbonate, sodium acetate or the like, but the process of the present invention is desirably carried out in the water or an aqueous alkaline solution at the room temperature.
The resulting hydrolyzed product is extracted with an appropriate organic solvent

REFERENCES:
patent: 3644374 (1972-02-01), Buijle et al.
patent: 4303667 (1981-12-01), Ueda et al.

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