Organic compounds -- part of the class 532-570 series – Organic compounds – Sulfur containing
Reexamination Certificate
2000-07-31
2002-06-04
Vollano, Jean F. (Department: 1621)
Organic compounds -- part of the class 532-570 series
Organic compounds
Sulfur containing
C568S033000, C568S035000
Reexamination Certificate
active
06399833
ABSTRACT:
TECHNICAL FIELD
The present invention relates to a process for producing an aryl vinyl sulfone solution, methods of transportation and storage of an aryl vinyl sulfone as a solution, and use thereof.
BACKGROUND ART
Aryl vinyl sulfones are useful compounds as intermediates of drugs or other products. The organic layers containing crude aryl vinyl sulfones, which can be obtained by various methods of production, may often be contaminated by impurities or the like in the production process, and it has been difficult to use these organic layers directly as intermediates of drugs or other products. Thus, there has been a need for the isolation of crystalline powder of aryl vinyl sulfones with low purity, which can be obtained by the concentration of the said organic layers, and for the subsequent purification of the crystalline powder by recrystallization or other techniques. At that time, one must handle the crystalline powder of aryl vinyl sulfones, so that some problems will be caused on the working atmosphere, such as dusting, from the viewpoints of safety and health. Therefore, handling methods without handling crystalline powder have been required.
In particular, phenyl vinyl sulfone as a typical compound has been known to exhibit irritation (Aldrich Material Safety Data). Further, it has been reported that one should pay attention for safety to the handling of vinylsulfonyl group-containing compounds (Chemtech, November, 34 (1996)). Therefore, the development of methods without handling solids of aryl vinyl sulfones, by which aryl vinyl sulfones can be handled safely and healthily, has been desired.
OBJECTS OF THE INVENTION
The main object of the present invention is to provide a method for handling aryl vinyl sulfones safely and healthily without handling solids of aryl vinyl sulfones.
This object and the other objects, as well as the advantages, of the present invention are explained below.
SUMMARY OF THE INVENTION
The present inventors have studied processes of production as well as methods of transportation and storage without handling powder of aryl vinyl sulfones, thereby completing the present invention.
That is, the present invention provides a process for producing a purified aryl vinyl sulfone solution, characterized in that an aryl vinyl sulfone is crystallized from an organic solvent solution of a crude aryl vinyl sulfone to give a crystallization mixture, and a wet cake of the aryl vinyl sulfone obtained by the separation of the solution from the said mixture is dissolved in a solution-forming solvent selected from ethers of 4 to 8 carbon atoms, aromatic hydrocarbons of 6 to 10 carbon atoms, halogenated hydrocarbons of 1 to 6 carbon atoms, ketones of 3; to 8 carbon atoms, esters of 3 to 6 carbon atoms, and nitriles of 2 to 6 carbon atoms; methods of transportation and storage of a purified aryl vinyl sulfone as a solution; and use thereof.
DETAILED DESCRIPTION OF THE INVENTION
First, the following explains a process for producing a purified aryl vinyl sulfone solution, characterized in that an aryl vinyl sulfone is crystallized from an organic solvent solution of a crude aryl vinyl sulfone to give a crystallization mixture, and a wet cake of the aryl vinyl sulfone obtained by the separation of the solution from the said mixture is dissolved in a solution-forming solvent selected from ethers of 4 to 8 carbon atoms, aromatic hydrocarbons of 6 to 10 carbon atoms, halogenated hydrocarbons of 1 to 6 carbon atoms, ketones of 3 to 8 carbon atoms, esters of 3 to 6 carbon atoms, and nitrites of 2 to 6 carbon atoms.
The organic solvent solution of a crude aryl vinyl sulfone as used in the present invention may include, for example, organic solvent solutions containing the crude aryl vinyl sulfone, which can be obtained by ordinary post-reaction treatments such as neutralization and water washing or by optional treatments such as desalting, from a reaction mixture obtained by the base treatment of a &bgr;-haloethyl aryl sulfone, a &bgr;-sulfate ethyl aryl sulfone, a &bgr;-tosyloxyethyl aryl sulfone, a &bgr;-mesyloxyethyl aryl sulfone or a &bgr;-nitrate ethyl aryl sulfone, or from a reaction mixture obtained by the oxidation of a vinyl aryl sulfide.
More particularly, the crude aryl vinyl sulfone in the present invention may include those containing a compound obtained by the treatment of a compound of formula (I):
wherein R
1
and R
2
are the same or different and are independently hydrogen, halogen, lower alkyl, lower alkoxy, nitro, amino, lower alkylamino, or di(lower alkyl)amino, and L is a leaving group, with a base; or those containing a compound of formula (III):
wherein R
1
and R
2
are as defined above, which is obtained by the oxidation of an aryl vinyl sulfide compound of formula (II):
wherein R
1
and R
2
are as defined above.
The atoms or groups represented by R
1
or R
2
in formulas (I), (II), and (III) are defined as follows:
The halogen atom may include, for example, fluorine, chlorine, bromine, and iodine atoms;
The lower alkyl group may include, for example, straight chain or branched alkyl groups of 1 to 6 carbon atoms, such as methyl, ethyl, n-propyl, n-butyl, n-pentyl, i-propyl, i-butyl, sec-butyl, t-butyl, neopentyl, and n-hexyl groups.
The lower alkoxy group may include, for example, straight chain or branched alkoxy groups of 1 to 6, carbon atoms, such as methoxy, ethoxy, n-propoxy, n-butoxy, n-pentoxy, i-propoxy, i-butoxy, sec-butoxy, t-butoxy, neo-pentoxy, and n-hexyloxy groups.
The lower alkylamino group refers to an amino group substituted with one lower alkyl group, in which the lower alkyl group may include the same groups as described above. Examples of the lower alkylamino group are methylamino, ethylamino, and t-butylamino groups. The di(lower alkyl)amino group refers to an amino group substituted with two lower alkyl groups, in which the lower alkyl groups may include the same groups as described above. Examples of the di(lower alkyl)amino group are dimethylamino, diethylamino, methylethylamino, and t-butylmethylamino groups.
The leaving group represented by L in formula (I) may include sulfate (OSO
3
H), nitrate (ONO
2
), and sulfonyloxy (e.g., tosyloxy, mesyloxy) groups, and halogen (chlorine, bromine, iodine) atoms.
Specific compounds of formula (I) may include compounds containing the leaving groups as described above, respectively, in the following aryl vinyl sulfones.
The base for use in the treatment of a compound of formula (I) may include inorganic or organic bases, or mixtures thereof The inorganic base may be hydroxides (sodium hydroxide, potassium hydroxide, lithium hydroxide), or carbonates or bicarbonates (sodium carbonate, potassium carbonate, sodium hydrogencarbonate, potassium hydrogencarbonate), of alkali metals or alkaline earth metals.
The organic base may include mono-, di-, or trialkylamines (triethylamine) and pyridine compounds. For example, there can be mentioned the disclosures of [J. Org. Chem., 58, 4506 (1993), J. Chem. Soc., 1754 (1949)], [JP-A 10-251219], [German Patent No. 842,198 (1942)], [Bull. Korean Chem. Soc., 16, 670 (1995)], [JP-A 10-36337], and [JP-A 10-195039]; and methods in accordance with these disclosures.
The aryl vinyl sulfide of formula (II) may include aryl vinyl sulfide compounds corresponding to the aryl vinyl sulfones as described below.
Specific examples of the aryl vinyl sulfone are phenyl vinyl sulfone, (4-chlorophenyl) vinyl sulfone, (3,4-dichlorophenyl) vinyl sulfone, (4-bromophenyl) vinyl sulfone, (4-fluorophenyl) vinyl sulfone, (4-iodophenyl) vinyl sulfone, (4-methylphenyl) vinyl sulfone, (2,4-dimethylphenyl) vinyl sulfone, (4-ethylphenyl) vinyl sulfone, (4-i-butylphenyl) vinyl sulfone, (4-t-butylphenyl) vinyl sulfone, (4-methoxyphneyl) vinyl sulfone, (3,4-dimethoxyphenyl) vinyl sulfone, (4-t-butoxyphenyl) vinyl sulfone, (3-aminophenyl) vinyl sulfone, (3-methylaminophenyl) vinyl sulfone, (3-ethylaminophenyl) vinyl sulfone, (3-dimethylaminophenyl) vinyl sulfone, (3-dimethylaminophenyl) vinyl sulfone, and (3-nitropheny
Kurihara Akio
Kurimoto Isao
Takano Naoyuki
Birch & Stewart Kolasch & Birch, LLP
Sumitomo Chemical Company Limited
Vollano Jean F.
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