Organic compounds -- part of the class 532-570 series – Organic compounds – Amino nitrogen containing
Patent
1999-05-24
2000-04-25
O'Sullivan, Peter
Organic compounds -- part of the class 532-570 series
Organic compounds
Amino nitrogen containing
564 99, C07C30344, C07C30338
Patent
active
060546131
DESCRIPTION:
BRIEF SUMMARY
The present invention relates to a process for the preparation of alkane-sulphonamides, in particular, to a process for obtaining a solution of an alkane-sulphonamide in a polar organic solvent.
Alkane- and arenesulphonamides are well known and are useful as intermediates in various aspects of chemistry, for example in the synthesis of herbicidally active compounds. Conventionally sulphonamides are produced by the reaction of a sulphonyl halide with the corresponding primary or secondary amine or ammonia, for example:
A variety of documents describe syntheses of this type in organic solvents, for example U.S. Pat. No. 5,455,377 discloses the use of an aliphatic nitrile, e.g. acetonitrile, as solvent, and EP 519235 discloses the use of dioxolane as solvent. The use of organic solvents has the disadvantage that it requires a recycle system and the containment of what are usually volatile and expensive solvents. In addition such processes result in the production of a solvent wet ammonium halide or amine hydrohalide which can cause disposal problems.
EP 439687 discloses a process for the production of alkane- and arenesulphonamides under boiling conditions in the absence of an additional solvent. This process has the drawback that it requires the use of anhydrous ammonia or amine. The ammonium halide or amine hydrohalide by-product which is produced in this reaction may be treated with an alkali metal hydroxide, e.g. sodium or potassium hydroxide, to give the corresponding alkali halide salt and free ammonia or alkylamine which can be recovered. The sulphonamide/salt mixture may be used directly for its intended purpose or the sulphonamide can be recovered from the salt by solvent extraction followed by filtration. As a comparative example EP 439687 discloses a process for the production of methanesulphonamide using aqueous ammonium hydroxide. However, in this particular example once the reaction is complete the water is evaporated under reduced pressure but no attempt is made to separate the resulting methanesulphonamide and ammonium chloride.
EP 333557 discloses a process for making arylsulphonamides from arylsulphonyl halides which results in a two-phase mixture.
The present invention provides a process for the preparation of a sulphonamide of formula: alkyl or C.sub.6 -C.sub.10 aryl; which comprises reacting the corresponding alkane- or arenesulphonyl halide of formula: mixture into a polar organic solvent.
The process of the invention may be performed as a batch, semi-continuous or continuous process.
Alkanesulphonamides produced according to the invention may contain straight chain, branched or cyclic C.sub.1 -C.sub.10 alkyl groups. The process is particularly useful for the preparation of short chain alkanesulphonamides, e.g. C.sub.1 -C.sub.4 alkanesulphonamides, especially methane- and ethanesulphonamide.
The sulphonyl halide of formula RSO.sub.2 Hal used as starting material is preferably a sulphonyl chloride.
When R.sup.1 and R.sup.2 represent C.sub.1 -C.sub.10 alkyl or C.sub.6 -C.sub.10 aryl particular groups they may represent include phenyl, naphthyl and straight chain, branched or cyclic C.sub.1 -C.sub.10 alkyl groups. However, R.sup.1 and R.sup.2 preferably represent hydrogen, i.e. the compound of formula NHR.sup.1 R.sup.2 is ammonia.
The starting materials required for the process are either commercially available or may be prepared by methods known to the skilled person.
In the process of the invention the sulphonyl halide is preferably added to an aqueous solution of the compound of formula NHR.sup.1 R.sup.2. The solution of the compound NHR.sup.1 R.sup.2 used in the reaction is preferably a 10-35% solution, more preferably a saturated solution. The mol ratio of compound NHR.sup.1 R.sup.2 to sulphonyl halide used in the reaction is preferably from about 2.5 to about 5.0, more preferably from 3.0 to 4.0. The addition of the sulphonyl halide to the reaction mixture is preferably conducted at a temperature of from ambient to about 80.degree. C., preferably at a temperature of from 25 to 50.degr
REFERENCES:
patent: 5455377 (1995-10-01), Ronchi et al.
Chem Abst., vol. 119, No. 9, Abstract No. 95095x, 1993.
Brown Stephen Martin
Gott Brian David
Muxworthy James Peter
O'Sullivan Peter
Thomson Marian T.
Zeneca Limited
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